EP3877488A1 - Use of a diester to improve the anti-wear properties of a lubricant composition - Google Patents
Use of a diester to improve the anti-wear properties of a lubricant compositionInfo
- Publication number
- EP3877488A1 EP3877488A1 EP19795025.6A EP19795025A EP3877488A1 EP 3877488 A1 EP3877488 A1 EP 3877488A1 EP 19795025 A EP19795025 A EP 19795025A EP 3877488 A1 EP3877488 A1 EP 3877488A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- linear
- formula
- branched
- weight
- methyl
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 119
- 150000005690 diesters Chemical class 0.000 title claims abstract description 63
- 239000000314 lubricant Substances 0.000 title claims abstract description 24
- 239000000654 additive Substances 0.000 claims abstract description 58
- 239000007866 anti-wear additive Substances 0.000 claims abstract description 29
- 230000000996 additive effect Effects 0.000 claims abstract description 17
- 230000001050 lubricating effect Effects 0.000 claims description 71
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 239000002199 base oil Substances 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 239000003963 antioxidant agent Substances 0.000 claims description 18
- 239000011701 zinc Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 239000003599 detergent Substances 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 229910052725 zinc Inorganic materials 0.000 claims description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 239000002270 dispersing agent Substances 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 150000002148 esters Chemical group 0.000 claims description 6
- 239000003921 oil Substances 0.000 claims description 6
- 239000002518 antifoaming agent Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000005069 Extreme pressure additive Substances 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- 239000004129 EU approved improving agent Substances 0.000 claims 1
- 239000008186 active pharmaceutical agent Substances 0.000 claims 1
- -1 amine phosphates Chemical class 0.000 description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- 239000002956 ash Substances 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 239000011574 phosphorus Substances 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229910052750 molybdenum Inorganic materials 0.000 description 4
- 239000011733 molybdenum Substances 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- BTHAQRDGBHUQMR-UHFFFAOYSA-N [S]P(=O)=O Chemical compound [S]P(=O)=O BTHAQRDGBHUQMR-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 150000003839 salts Chemical class 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
- 235000002918 Fraxinus excelsior Nutrition 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000000994 depressogenic effect Effects 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000010705 motor oil Substances 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 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
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 230000002028 premature Effects 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-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
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 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
- 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
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 230000003254 anti-foaming effect Effects 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 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
- 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
- 210000005053 lamin Anatomy 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 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 1
- 239000000178 monomer Substances 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 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
- 239000010452 phosphate Substances 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
- 229920006112 polar polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 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
- 239000007787 solid Substances 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
- 230000004936 stimulating effect Effects 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/68—Esters
- C10M129/74—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M2203/003—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
- 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
- C10M2205/02—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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
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- 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
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- 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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/071—Branched chain compounds
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- 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
- C10N2030/02—Pour-point; Viscosity index
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- 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
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- 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
- C10N2030/08—Resistance to extreme temperature
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- 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 lubricant compositions, in particular lubricant compositions for a vehicle engine, in particular for a motor vehicle engine. It relates more particularly to the use of new compounds, of the diester type, as additives in these lubricating compositions, in order to improve their anti-wear properties, while advantageously reducing the content of anti-wear additives which they comprise .
- Lubricating compositions also called “lubricants” are commonly used in engines for the main purpose of reducing the frictional forces between the various metal parts moving in the engines. They are also effective in preventing premature wear or even damage to these parts, and in particular their surface.
- a lubricating composition is conventionally composed of a base oil with which are generally associated several additives dedicated to stimulating the lubricating performance of the base oil, such as for example friction modifying additives, but also to provide additional performance.
- anti-wear additives are considered in order to reduce wear on the mechanical parts of the engine, and thus prevent degradation of the engine's durability.
- antiwear additives there may be mentioned in particular amine phosphates, or also phospho-sulfur additives, such as metal alkylthiophosphates, in particular zinc alkylthiophosphates, and more specifically zinc dialkyldithiophosphates or ZnDTP.
- Such compounds are preferably of formula Zn ((SP (S) (OR) (OR)) 2 , in which R and R, identical or different, independently represent an alkyl group, preferably an alkyl group comprising from 1 to 18 atoms of carbon.
- sulfur, phosphorus and sulphated ash can damage the post-treatment systems installed on vehicles. Ashes are harmful to particulate filters and phosphorus acts as poison for catalytic systems.
- the invention specifically aims to propose new compounds as additives to improve the anti-wear properties of a lubricating composition, in particular dedicated to an engine, and more particularly to a motor vehicle engine, comprising one or more anti-wear additives conventional.
- the present invention thus relates to the use of a diester of formula (I) below:
- - R represent, independently of each other, a hydrogen atom or a (Ci-Cs) alkyl group, linear or branched, in particular a methyl, ethyl or propyl group, in particular methyl;
- - n is 1, 2 or 3; it being understood that, when s is different from 1, n may be the same or different;
- R a and R b identical or different, represent, independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear chain of 2 to 11 carbon atoms, preferably 3 to 8 carbon atoms;
- a lubricating composition comprising one or more anti-wear additive (s).
- the anti-wear properties of a composition can be more particularly evaluated according to standard ASTM D2670.
- diesters of formula (I) thus makes it possible to lower the content of conventional anti-wear additives, and in particular in additives generating ash, phosphorus or sulfur, while retaining excellent performance in terms of anti-wear properties.
- the lowering of the content of antiwear additives advantageously makes it possible to meet the specifications of the "LOW SAPS" lubricating compositions.
- the additive used according to the invention is a diester or mixture of diesters of general formula (I) below:
- - R represent, independently of each other, a hydrogen atom or a (Ci-Cs) alkyl group, linear or branched, in particular a methyl, ethyl or propyl group, in particular methyl;
- n is 1, 2 or 3; in particular n is 2 or 3 and more particularly n is 2, it being understood that, when s is different from 1, n may be the same or different; and
- R a and R b identical or different, represent, independently of one another, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear chain of 2 to 11 carbon atoms, preferably 3 to 8 carbon atoms carbon;
- At least one of the groups R bonded to the carbon in beta position of the oxygen atoms of the ester functions represents a hydrogen atom.
- R a and R b identical or different, represent independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, comprising from 2 to 11 carbon atoms, preferably from 3 to 8 carbon atoms.
- diester of formula (I) implemented according to the invention will be designated more simply by diester of the invention.
- a carbon chain can have from t to z carbon atoms; for example Ci_ 4 a carbon chain which can have from 1 to 4 carbon atoms;
- alkyl a saturated, linear or branched aliphatic group
- a Ci-4-alkyl group represents a carbon chain of 1 to 4 carbon atoms, linear or branched, more particularly methyl, ethyl, propyl, isopropyl, butyl, isobutyl, fo / t-butylc.
- n in the above formula (I) is worth 2 or 3, and more particularly n is worth 2.
- At least one of the groups R represents a (Ci-Cs) alkyl group, in particular (Ci-C 4 ) alkyl, linear or branched, more preferably methyl, ethyl or propyl; advantageously methyl.
- the diester of formula (I) used according to the invention can more particularly be a diester of formula (F) below:
- R and R ’ represent, independently of each other, a hydrogen atom or a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, in particular a methyl group;
- R a and R b identical or different, represent, independently of one another, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear chain of 2 to 11 carbon atoms, preferably 3 to 8 carbon atoms carbon; provided that, when s is 2, at least one of the groups R or R 'represents a (Ci-Cs) alkyl group, linear or branched.
- a diester used according to the invention is of formula (F) in which at least one of the R or R ′ represents a (Ci-Cs) alkyl group, in particular (Ci-C 4 ) alkyl, linear or branched, more preferably methyl, ethyl or propyl; advantageously methyl.
- s in the above formula (I) or (F) is equal to 2.
- the diester used according to the invention can be of the following formula (Fa):
- R and R ’ represent, independently of each other, a hydrogen atom or a (Ci-Cs) alkyl group, linear or branched, in particular a methyl, ethyl or propyl group, advantageously methyl;
- R a and R b identical or different, represent independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear chain of 2 to 11 carbon atoms, preferably 3 to 8 atoms carbon;
- At least one of the groups R or R ′ represents a (Ci-Cs) alkyl group, linear or branched, in particular methyl, ethyl or propyl, advantageously methyl.
- At least one of the groups R represents a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl; and at least one of the R ’represents a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl.
- the diester used according to the invention may be of formula (Fa) in which one of the groups R represents a (Ci-Cs) alkyl group, linear or branched, in particular a methyl, ethyl or propyle, advantageously methyl; and one of the groups R ′ represents a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl; the other groups R and R ′ representing hydrogen atoms.
- one of the groups R represents a (Ci-Cs) alkyl group, linear or branched, in particular a methyl, ethyl or propyle, advantageously methyl
- one of the groups R ′ represents a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl
- the other groups R and R ′ representing hydrogen atoms.
- the diester used according to the invention can have the following formula (I ”a):
- R 1 and R 2 represents a (Ci-Cs) alkyl group, linear or branched, the other representing a hydrogen atom;
- R 3 and R 4 represents a (Ci-Cs) alkyl group, linear or branched, the other representing a hydrogen atom;
- R a and R b identical or different, are as defined above.
- diester used according to the invention can be of formula (I ”a) in which:
- R 1 and R 2 represents a methyl, ethyl or propyl group, advantageously methyl, the other representing a hydrogen atom;
- one of the groups R 3 and R 4 represents a methyl, ethyl or propyl group, advantageously methyl, the other representing a hydrogen atom.
- the diester used according to the invention can have the following formula (F b):
- - R represent, independently of each other, a hydrogen atom or a (Ci-Cs) alkyl group, linear or branched, in particular a methyl, ethyl or propyl group, advantageously methyl;
- - n is 2; - R a and R b , identical or different, represent independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear chain of 2 to 11 carbon atoms, preferably 3 to 8 atoms carbon.
- At least one of the R represents a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl.
- the diester used according to the invention may be of formula (I'b) in which one of the groups R represents a (Ci-C5) alkyl group, linear or branched, in particular a methyl, ethyl or propyl group , advantageously methyl, the others representing hydrogen atoms.
- R a and R b in formula (I), (F), (a), (I ”a) or (I'b) above, identical or different, represent hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear chain of 2 to 11 carbon atoms, preferably 3 to 8 carbon atoms.
- hydrocarbon group is understood to mean any group having a carbon atom directly attached to the rest of the molecule and having mainly an aliphatic hydrocarbon character.
- R a and R b in the formula (I), (F), (a), (I ”a) or (I'b) mentioned above, have a linear chain of 3 to 6 carbon atoms.
- R a and R b in formula (I), (F), (a), (I ”a) or (I'b) above have a linear sequence of 8 to 11 atoms of carbon.
- linear chain from t to z carbon atoms is meant a saturated or unsaturated carbon chain, preferably saturated, comprising from t to z carbon atoms one after the other, the carbon atoms possibly present at the level ramifications of the carbon chain not being taken into account in the number of carbon atoms (tz) constituting the linear chain.
- R a and R b are derived from vegetable, animal or petroleum origin.
- R a and R b identical or different, represent groups saturated.
- R a and R b identical or different, represent groups linear.
- R a and R b represent linear hydrocarbon groups saturated in C H to C II , in particular Cs to Cio.
- R a and R b are identical.
- R a and R b both represent groups "-octylc or" -undécylc, preferably "-octylc.
- R a and R b represent branched hydrocarbon groups comprising 2 to 11 carbon atoms, preferably 3 to 8 carbon atoms.
- the diesters of formula (I) used according to the invention may be commercially available or prepared according to synthesis methods described in the literature and known to those skilled in the art. These synthetic methods more particularly implement an esterification reaction between a diol compound of formula H0 - ([[C (R) 2 ] n -0) s -0H and compounds of formula R a -COOH and R b - COOH, with R a and R b , identical or different, being as defined above.
- diesters of the above formula (I), in particular of the above formula (F) can be obtained by esterification reaction between a mono- or polypropylene glycol, in particular monopropylene glycol (MPG) or dipropylene glycol (DPG), and one or more suitable carboxylic acids R a -COOH and R b -COOH.
- MPG monopropylene glycol
- DPG dipropylene glycol
- - s is 2, one of the groups R representing a (Ci-Cs) alkyl group, linear or branched, in particular a methyl, ethyl or propyl group, advantageously methyl, the others representing hydrogen atoms; and
- one of the groups R ’ representing a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl, the others representing hydrogen atoms,
- DPG dipropylene glycol
- R a -COOH and R b -COOH can be obtained via an esterification reaction between dipropylene glycol (DPG) and one or more suitable carboxylic acids R a -COOH and R b -COOH.
- one of the groups R representing a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl, the others representing hydrogen atoms,
- MPG monopropylene glycol
- R a -COOH and R b -COOH can be obtained via an esterification reaction between monopropylene glycol (MPG) and one or more suitable carboxylic acids R a -COOH and R b -COOH.
- such a diester or mixture of diesters can thus be obtained by esterification reaction between monopropylene glycol or dipropylene glycol and nonanoic acid or dodecanoic acid.
- diester of formula (I) as defined above may be in the form of a mixture of diesters of formula (I) as defined above.
- the diesters of formula (I) are used as additives in a lubricating composition, in particular in a lubricating composition for an engine, in particular for a vehicle, and more preferably for a motor vehicle engine.
- the said diesters or diesters of formula (I) can be used in a lubricating composition, in a proportion of 1% to 30% by weight, in particular from 5% to 30% by weight, in particular from 5 % to 25% by weight, preferably from 5% to 20% by weight, relative to the total weight of the lubricating composition.
- Anti-wear additives preferably from 5% to 20% by weight, relative to the total weight of the lubricating composition.
- a lubricating composition considered according to the invention comprises one or more conventional anti-wear additives.
- anti-wear additive is intended to denote a compound which, used in a lubricating composition, in particular a lubricating composition for a vehicle engine, in particular for a motor vehicle engine, makes it possible to improve the anti-wear properties of the composition.
- anti-wear additives such as for example polysulphide additives, sulfur olefin additives or phospho-sulfur 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) (OR ')) 2 , in which R and R', identical or different, represent, independently of one another, alkyl groups, linear or branched, preferably branched, preferably comprising from 1 to 18 carbon atoms, preferably at least one of the groups R and R ′ represents an alkyl group, preferably branched, having at least 6 carbon atoms, in particular having 6 to 18 carbon atoms.
- the diesters of formula (I) according to the invention are used in a lubricating composition in combination with one or more additives of the zinc dialkyldithiophosphate type, in particular of formula Zn (( SP (S) (OR) (OR ')) above.
- a lubricating composition considered according to the invention may comprise from 0.01 to 6% by weight, preferably from 0.05 to 4% by weight, more preferably from 0.1 to 2% by weight, relative to the total weight of the composition, anti-wear additives.
- the use of one or more diesters of formula (I) according to the invention advantageously makes it possible to improve the anti-wear properties of the lubricating composition. According to the invention, this results in the possibility of obtaining a lubricating composition having excellent anti-wear properties, while lowering the content of conventionally used anti-wear additives.
- the anti-wear additive (s), in particular sulfur or phosphorus generators are present in a lubricating composition in a content less than or equal to 2% by weight, in particular less than or equal to 1% by weight.
- a lubricating composition typically comprises, in addition to one or more diesters of formula (I) as defined above, in combination with one or more conventional anti-wear additives, one or more base oils, as well as other additives, conventionally considered in lubricating compositions.
- the diester (s) of formula (I) can be added to an oil or mixture of base oils, then the other additional additives, including the anti-wear additive (s), added.
- ester (s) of formula (I) can be added to a conventional pre-existing lubricant formulation, comprising in particular one or more base oils and additional additives, in particular one or more anti-wear additives.
- a lubricant composition for an engine can be supplemented with one or more diesters of formula (I) in accordance with the invention by adding, for example, the said diester (s) directly to the reservoir previously filled with a conventional formulation of lubricant.
- a lubricating composition considered according to the invention can thus also comprise one or more base oils distinct from the diesters of formula (I).
- base oils can be chosen from the base oils conventionally used in the field of lubricating oils, such as mineral, synthetic or natural, animal or vegetable oils or their mixtures.
- It can be a mixture of several base oils, for example a mixture of two, three, or four base oils.
- the base oils of the lubricating compositions considered according to the invention may in particular be oils of mineral or synthetic origins belonging to the groups I to V according to the classes defined in the API classification (or their equivalents according to the ATIEL classification) and presented in table A below or their mixtures, provided that they are distinct from the diesters of the invention.
- Mineral base oils 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, hydrotreating, hydrocracking, hydroisomerization and hydro finish.
- the synthetic base oils can be esters of carboxylic acids and alcohols, polyalphaolefins or else polyalkylene glycol (PAG) obtained by polymerization or copolymerization of alkylene oxides comprising from 2 to 8 carbon atoms, in particular from 2 to 4 carbon atoms.
- the polyalphaolefins used as base oils are for example obtained from monomers comprising 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 standard ASTM D445.
- Their average molecular weight is generally between 250 and 3000 according to standard ASTM D5296.
- Mixtures of synthetic and mineral oils which can be bio-sourced, can also be used.
- base oils There is generally no limitation as to the use of different base oils in the lubricating composition, except that they must have properties, in particular viscosity, viscosity index, sulfur content. or resistance to oxidation, suitable for use in vehicle engines.
- a lubricating composition considered according to the invention comprises at least one base oil chosen from group II, III and IV oils of the API classification, and their mixtures.
- such a lubricating composition can comprise at least one group III base oil.
- a lubricating composition considered according to the invention may comprise at least 50% by weight of base oil (s) relative to its total weight, in particular at least 60% by weight of base oil (s), and more particularly between 60 and 99% by weight of base oil (s).
- the group III oil or oils represent (s) at least 50% by weight, in particular at least 60% by weight of the total weight of the base oils of the composition.
- a lubricant composition considered according to the invention may also further comprise all types of additives, suitable for use in a lubricant for a vehicle engine, in particular for a motor vehicle.
- additives can be introduced in isolation and / or in the form of a mixture like those already available for sale for formulations of commercial lubricants for vehicle engines, with performance levels as defined by ACEA ( Association of European Automobile Manufacturers) and / or API (American Petroleum Institute), well known to those skilled in the art.
- ACEA Association of European Automobile Manufacturers
- API American Petroleum Institute
- a lubricating composition considered according to the invention may comprise at least one friction-modifying additive.
- the friction modifying additives can be chosen from compounds providing metallic elements and ash-free compounds.
- transition metal complexes such as Mo, Sb. Sn, Fe, Cu, Zn, the ligands of which can be hydrocarbon compounds comprising oxygen, nitrogen, sulfur or phosphorus atoms.
- the ash-free friction-modifying additives are generally of organic origin and can be chosen from monoesters of fatty acids and of polyols, alkoxylated amines, alkoxylated fatty amines, fatty epoxides, fatty borate epoxides, amines fatty or fatty acid glycerol esters.
- the fatty compounds comprise at least one hydrocarbon group comprising from 10 to 24 carbon atoms.
- a lubricating composition comprises at least one friction-modifying additive, in particular based on molybdenum.
- the molybdenum-based compounds can be chosen from molybdenum dithiocarbamates (Mo-DTC), molybdenum dithiophosphates (Mo-DTP), and their mixtures.
- a lubricating composition comprises at least one Mo-DTC compound and at least one Mo-DTP compound.
- a lubricating composition can in particular comprise a molybdenum content of between 1000 and 2500 ppm.
- such a composition makes it possible to make additional fuel savings.
- a lubricating composition considered according to the invention can comprise from 0.01 to 5% by weight, preferably from 0.01 to 5% by weight, more particularly from 0.1 to 2% by weight or even more particularly from 0.1 to 1.5% by weight, relative to the total weight of the lubricating composition, of friction-modifying additives, advantageously including at least one friction-modifying additive based on molybdenum.
- a lubricating composition considered according to the invention can comprise at least one antioxidant additive.
- Antioxidant additives are essentially dedicated to delaying the degradation of the lubricating composition in service. This degradation can in particular be reflected by the formation of deposits, by the presence of sludge or by an increase in the viscosity of the lubricating composition. They act in particular as radical inhibitors or destroyers of hydroperoxides.
- antioxidant additives commonly used there may be mentioned antioxidants of the phenolic type, the antioxidant additives of the amino type, the phosphosulfurized antioxidant additives. Some of these antioxidant additives, for example phosphosulfur antioxidant additives, can generate ash.
- the phenolic antioxidant additives may be ash-free or may 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, dipheny lamines, diphenylamines substituted by 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 in which at least one vicinal carbon of the carbon carrying the alcohol function is substituted by at least one C 1 -C 10 alkyl group, preferably a C 1 -C 6 alkyl group. ,, preferably a C 4 alkyl group, preferably by the ter-butyl group.
- Amino compounds are another class of antioxidant additives that can be used, possibly in combination with phenolic antioxidant additives.
- Examples of amino compounds are the aromatic amines, for example the aromatic amines of formula NR 5 R 6 R 7 in which R 5 represents an aliphatic group or an aromatic group, optionally substituted, R 6 represents an aromatic group, optionally substituted, R 7 represents a hydrogen atom, an alkyl group, an aryl group or a group of formula R 8 S (0) z R 9 in which R 8 represents an alkylene group or an alkenylene group, R 9 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.
- a lubricating composition considered according to the invention can contain all types of antioxidant additives known to the skilled person.
- the lubricating composition comprises at least one antioxidant additive free from ash.
- a lubricating composition considered according to the invention may comprise from 0.1 to 2% by weight, relative to the total weight of the composition, of at least one antioxidant additive.
- a lubricating composition considered according to the invention may comprise at least one detergent additive.
- So-called detergent additives generally reduce the formation of deposits on the surface of metal parts by dissolving secondary oxidation and combustion products.
- Detergent additives 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 metal cation of an alkali or alkaline earth metal.
- the detergent additives are preferably chosen from the alkali metal or alkaline earth metal salts of carboxylic acids, the sulfonates, the salicylates, the naphthenates, as well as the phenate salts.
- the alkali and alkaline earth metals are preferably calcium, magnesium, sodium or barium. These metal salts generally include the metal in a stoichiometric amount or in excess, therefore in an amount greater than the stoichiometric amount.
- overbased detergent additives the excess metal bringing the overbased character to the detergent additive is then generally in the form of a metal salt insoluble in the base oil, for example a carbonate, a hydroxide, an oxalate, an acetate, a glutamate, preferably a carbonate.
- a metal salt insoluble in the base oil for example a carbonate, a hydroxide, an oxalate, an acetate, a glutamate, preferably a carbonate.
- the detergent additives are generally used in a content ranging from 0.5 to 8%, preferably from 0.5 to 4% by weight, relative to the total weight of the lubricating composition.
- they are present in a content of less than 4% by weight, in particular less than 2% by weight, in particular less than 1% by weight, or even the lubricating composition is free from detergent additive (s).
- a lubricant composition considered according to the invention may comprise at least one pour point depressant additive (also called "PPD" agents for "Pour Point Depressant” in English). By slowing the formation of paraffin crystals, pour point lowering additives generally improve the cold behavior of the lubricant composition.
- pour point reducing agents examples include polyalkyl methacrylates, polyacrylates, polyarylamides, polyalkylphenols, polyalkylnaphthalenes and alkylated polystyrenes.
- a lubricating composition considered according to the invention can also comprise at least one dispersing agent.
- the dispersing agents ensure the suspension and the evacuation of the insoluble solid contaminants constituted by the secondary oxidation products which are formed when the lubricating composition is in use. They can be chosen from Mannich bases, succinimides and their derivatives.
- a lubricating composition considered according to the invention can comprise from 0.2 to 10% by weight of dispersing agent (s), relative to the total weight of the composition.
- a lubricant composition considered according to the invention can also comprise at least one viscosity index (VI) improver.
- the viscosity index improvers (VI) make it possible to guarantee good resistance to cold and minimum viscosity at high temperature.
- polymer improving the viscosity index mention may be made of polymeric esters, homopolymers or copolymers, hydrogenated or non-hydrogenated of styrene, butadiene and isoprene, homopolymers or copolymers of olefin, such than ethylene or propylene, polyacrylates and polymethacrylates (PMA).
- a lubricating composition considered according to the invention may comprise from 1 to 15% by weight, of additive (s) improving the viscosity index, relative to the total weight of the lubricating composition.
- a lubricating composition considered according to the invention may also comprise at least anti-foam additive.
- the anti-foam additives can be chosen from polar polymers such as polymethylsiloxanes or polyacrylates.
- a lubricating composition considered according to the invention may comprise from 0.01 to 3% by weight of anti-foaming additive (s), relative to the total weight of the lubricating composition.
- the use of one or more diesters of formula (I) required according to the invention as an additive makes it possible to significantly improve the anti-wear properties of the lubricating composition comprising one or more anti-wear additives conventional.
- the anti-wear properties can be evaluated according to a procedure based on standard ASTM D2670, via the use of a tribometer, as described in the examples which follow.
- a lubricating composition considered according to the invention can more particularly be a grade composition according to the SAEJ300 classification defined by the formula (X) W (Y), in which X represents 0 or 5; and Y represents an integer ranging from 4 to 30.
- This grade qualifies a selection of lubricant compositions specially intended for an engine application of a motor vehicle and which in particular satisfy specific characteristics quantified with respect to various parameters such as the viscosity at cold at start-up, cold pumpability, kinematic viscosity at low shear rate and dynamic viscosity at high shear rate.
- the viscosity grade of a lubricating composition considered according to the invention can in particular be chosen from:
- Y represents an integer ranging from 4 to 20, in particular ranging from 4 to 16 or from 4 to 12;
- the grade according to the SAEJ300 classification of a lubricating composition considered according to the invention is chosen from 0W4, 0W8, 0W12, 0W16, 0W20, 5W4, 5W8, 5W12, 5W16 and 5W20, preferably chosen from 0W4, 0W8, 0W12, 0W16, 0W20 and 5W20.
- a lubricating composition considered according to the invention may have a grade according to the SAEJ300 classification of 0W20 or 0W16.
- the kinematic viscosity measured at 100 ° C. according to standard ASTM D445 of a lubricating composition considered according to the invention is between 3 and 15 mm 2 . s 1 , in particular between 3 and 13 mm 2 . s 1 .
- the viscosity measured at high temperature and high shear, HTHS (for “high temperature high-shear viscosity measurement” in English), measured at 150 ° C, is equal to or greater than 1.7 mPa.s, preferably between 1.7 and 3.7 mPa.s, advantageously between 2.3 and 3.7 mPa.s.
- the HTHS measurement is carried out at high shear (10 6 s 1 ) and at 150 ° C. according to the standardized methods CEC-L-36-A-90, ASTM D4683 and ASTMD4741.
- Lubricating compositions in accordance with the invention (II and 12), using a diester of formula (I), and comparative compositions (Cl and C2), free of diester of formula (I), were formulated with the components and quantities (expressed as percentage by mass) indicated in Table 1 below.
- One conventional additive package comprising an anti-wear additive (bis (dithiophosphate) and zinc bis [0,0-bis (2-ethylhexyl) phthalate], for example, sold under the name "OLOA 269R ®”), agents antioxidants, a friction modifying agent, a dispersant and detergents,
- Conventional additive package 2 including an anti-wear additive (zinc bis [0- (1,3-dimethylbutyl)] bis [0- (isopropyl)] bis (dithiophosphate)), antioxidants, a friction modifier , a dispersant and detergents,
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Abstract
The present invention relates to the use of a diester of the following formula (I): Ra-C(O)-O-([C(R)2]n-O)s-C(O)-Rb(I), as an additive to improve the anti-wear properties of a lubricant composition comprising one or more anti-wear additive(s).
Description
UTILISATION D'UN DIESTER POUR AMELIORER LES PROPRIETES ANTI-USURE USE OF A DIESTER TO IMPROVE ANTI-WEAR PROPERTIES
D'UNE COMPOSITION LUBRIFIANTE OF A LUBRICATING COMPOSITION
La présente invention concerne le domaine des compositions lubrifiantes, notamment des compositions lubrifiantes pour moteur de véhicule, en particulier pour moteur de véhicule automobile. Elle concerne plus particulièrement l’utilisation de nouveaux composés, de type diesters, à titre d’additifs dans ces compositions lubrifiantes, afin d’améliorer leurs propriétés anti-usure, tout en réduisant avantageusement la teneur en additifs anti-usure qu’elles comprennent. The present invention relates to the field of lubricant compositions, in particular lubricant compositions for a vehicle engine, in particular for a motor vehicle engine. It relates more particularly to the use of new compounds, of the diester type, as additives in these lubricating compositions, in order to improve their anti-wear properties, while advantageously reducing the content of anti-wear additives which they comprise .
Les compositions lubrifiantes, dites encore « les lubrifiants », sont communément mises en œuvre dans les moteurs à des fins principales de réduction des forces de frottement entre les différentes pièces métalliques en mouvement dans les moteurs. Elles sont en outre efficaces pour prévenir une usure prématurée voire un endommagement de ces pièces, et en particulier de leur surface. Lubricating compositions, also called "lubricants", are commonly used in engines for the main purpose of reducing the frictional forces between the various metal parts moving in the engines. They are also effective in preventing premature wear or even damage to these parts, and in particular their surface.
Pour ce faire, une composition lubrifiante est classiquement composée d’une huile de base à laquelle sont généralement associés plusieurs additifs dédiés à stimuler les performances lubrifiantes de l’huile de base, comme par exemple des additifs modificateurs de frottement, mais aussi à procurer des performances supplémentaires. To do this, a lubricating composition is conventionally composed of a base oil with which are generally associated several additives dedicated to stimulating the lubricating performance of the base oil, such as for example friction modifying additives, but also to provide additional performance.
En particulier, des additifs dits « anti-usure » sont considérés afin de réduire l’usure des pièces mécaniques du moteur, et ainsi prévenir une dégradation de la durabilité du moteur. Parmi ces additifs anti-usure, on peut citer notamment les phosphates d’amine, ou encore des additifs phospho-soufrés, comme les alkylthiophosphates métalliques, en particulier les alkylthiophosphates de zinc, et plus spécifiquement les dialkyldithiophosphates de zinc ou ZnDTP. De tels composés sont préférentiellement de formule Zn((SP(S)(OR )(OR ))2, dans laquelle R et R , identiques ou différents, représentent indépendamment un groupement alkyle, préférentiellement un groupement alkyle comportant de 1 à 18 atomes de carbone. In particular, so-called “anti-wear” additives are considered in order to reduce wear on the mechanical parts of the engine, and thus prevent degradation of the engine's durability. Among these antiwear additives, there may be mentioned in particular amine phosphates, or also phospho-sulfur additives, such as metal alkylthiophosphates, in particular zinc alkylthiophosphates, and more specifically zinc dialkyldithiophosphates or ZnDTP. Such compounds are preferably of formula Zn ((SP (S) (OR) (OR)) 2 , in which R and R, identical or different, independently represent an alkyl group, preferably an alkyl group comprising from 1 to 18 atoms of carbon.
Des additifs anti-usure alternatifs, de type tungstate d’amine ou phosphate d’amine, ou encore des complexes à base de zinc de formule spécifique, ont également été décrits, en combinaison avec des polyalkylène glycols, dans les demandes WO 2017/157892 et WO 2017/157979. Alternative anti-wear additives, of the amine tungstate or amine phosphate type, or even zinc-based complexes of specific formula, have also been described, in combination with polyalkylene glycols, in applications WO 2017/157892 and WO 2017/157979.
Malheureusement, l’emploi, dans les lubrifiants moteurs, de ces additifs, à base de phosphore et/ou de souffre, et générateurs de cendres, est indésirable pour répondre aux
spécifications en termes de « bas taux de cendres » (LOW SAPS). Ces spécifications, élaborées par l’Association des Constructeurs Automobiles Européens (ACE A), imposent aux compositions lubrifiantes des teneurs limites en cendres sulfatées (générées par la présence de métaux), en soufre et en phosphore, d’où l’appellation « Low SAPS » pour « Low Sulfated Ashes, Phosphorus, Sulfur ». Unfortunately, the use in engine lubricants of these additives, based on phosphorus and / or sulfur, and ash generators, is undesirable to meet the specifications in terms of “low ash rate” (LOW SAPS). These specifications, developed by the Association of European Automobile Manufacturers (ACE A), impose limits on lubricating compositions in sulphated ash (generated by the presence of metals), sulfur and phosphorus, hence the name "Low SAPS ”for“ Low Sulfated Ashes, Phosphorus, Sulfur ”.
En effet, le soufre, le phosphore et les cendres sulfatées peuvent endommager les systèmes de post traitements installés sur les véhicules. Les cendres sont néfastes pour les filtres à particules et le phosphore agit comme poison des systèmes catalytiques. In fact, sulfur, phosphorus and sulphated ash can damage the post-treatment systems installed on vehicles. Ashes are harmful to particulate filters and phosphorus acts as poison for catalytic systems.
Abaisser les taux de cendres, de soufre et de phosphore dans les lubrifiants moteurs, tout en maintenant les hauts niveaux de performances requis, demeure un défi, car ces éléments sont présents dans les additifs les plus couramment employés. Lowering the levels of ash, sulfur and phosphorus in engine lubricants, while maintaining the high performance levels required, remains a challenge, since these elements are present in the most commonly used additives.
En particulier, il serait souhaitable de pouvoir abaisser le taux en additifs anti usure d’un lubrifiant, aux fins de respecter les teneurs limites imposées pour les lubrifiants « Low SAPS », tout en conservant, voire même en améliorant les propriétés anti-usure du lubrifiant, essentielles pour prévenir une dégradation prématurée du moteur. In particular, it would be desirable to be able to lower the level of anti-wear additives in a lubricant, in order to comply with the limit contents imposed for “Low SAPS” lubricants, while retaining or even improving the anti-wear properties of the lubricant, essential to prevent premature engine degradation.
L’invention vise précisément à proposer de nouveaux composés comme additifs pour améliorer les propriétés anti-usure d’une composition lubrifiante, en particulier dédiée à un moteur, et plus particulièrement à un moteur de véhicule automobile, comprenant un ou plusieurs additifs anti-usure conventionnels. The invention specifically aims to propose new compounds as additives to improve the anti-wear properties of a lubricating composition, in particular dedicated to an engine, and more particularly to a motor vehicle engine, comprising one or more anti-wear additives conventional.
La présente invention a ainsi pour objet l’utilisation d’un diester de formule (I) suivante : The present invention thus relates to the use of a diester of formula (I) below:
Ra-C(0)-0-([C(R)2]n-0)s-C(0)-Rb (I) R a -C (0) -0 - ([C (R) 2 ] n -0) s -C (0) -R b (I)
dans laquelle : in which :
- R représentent, indépendamment les uns des autres, un atome d’hydrogène ou un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, notamment méthyle ; - R represent, independently of each other, a hydrogen atom or a (Ci-Cs) alkyl group, linear or branched, in particular a methyl, ethyl or propyl group, in particular methyl;
- s vaut 1 ou 2 ; - s is 1 or 2;
- n vaut 1, 2 ou 3 ; étant entendu que, lorsque s est différent de 1 , n peuvent être identiques ou différents ; et - n is 1, 2 or 3; it being understood that, when s is different from 1, n may be the same or different; and
- Ra et Rb, identiques ou différents, représentent indépendamment les uns des autres, des groupements hydrocarbonés, saturés ou insaturés, linéaires ou ramifiés,
présentant un enchaînement linéaire de 2 à 11 atomes de carbone, de préférence de 3 à 8 atomes de carbone ; - R a and R b , identical or different, represent, independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear chain of 2 to 11 carbon atoms, preferably 3 to 8 carbon atoms;
sous réserve que, lorsque s vaut 2 et n, identiques, valent 2, au moins l’un des groupe R représente un groupe (Ci-Cs)alkyle, linéaire ou ramifié ; et with the proviso that, when s is 2 and n, which are identical, are 2, at least one of the group R represents a (Ci-Cs) alkyl group, linear or branched; and
sous réserve que, lorsque s vaut 1 et n vaut 3, au moins l’un des groupes R lié au carbone en position bêta des atomes d’oxygène des fonctions esters représente un atome d’hydrogène, with the proviso that, when s is 1 and n is 3, at least one of the groups R bonded to the carbon in beta position of the oxygen atoms of the ester functions represents a hydrogen atom,
à titre d’additif pour améliorer les propriétés anti-usure d’une composition lubrifiante comprenant un ou plusieurs additif(s) anti-usure. as an additive for improving the anti-wear properties of a lubricating composition comprising one or more anti-wear additive (s).
Comme illustré dans les exemples qui suivent, les inventeurs ont constaté que l’ajout de tels diesters de formule (I) dans une composition lubrifiante comprenant un ou plusieurs additifs anti-usure classiquement mis en œuvre, tels que le ZnDTP, permet d’obtenir des propriétés anti-usure signifîcativement améliorées comparativement à celles obtenues avec une composition lubrifiante mettant en œuvre uniquement un ou plusieurs additifs anti-usure. As illustrated in the examples which follow, the inventors have found that the addition of such diesters of formula (I) in a lubricating composition comprising one or more conventionally used anti-wear additives, such as ZnDTP, makes it possible to obtain significantly improved anti-wear properties compared to those obtained with a lubricating composition using only one or more anti-wear additives.
Les propriétés anti-usure d’une composition peuvent être plus particulièrement évaluées selon la norme ASTM D2670. The anti-wear properties of a composition can be more particularly evaluated according to standard ASTM D2670.
Par conséquent, de manière avantageuse, il est possible d’accéder, via la mise en œuvre d’un ou plusieurs diesters de formule (I) selon l’invention, à une composition lubrifiante présentant d’excellentes propriétés anti-usure, voire des propriétés anti-usure améliorées, tout en utilisant des quantités moindres d’additifs anti-usure, par rapport à une composition lubrifiante classique ne comprenant pas de diester selon l’invention. Consequently, advantageously, it is possible to access, via the use of one or more diesters of formula (I) according to the invention, to a lubricating composition having excellent anti-wear properties, or even improved antiwear properties, while using lower amounts of antiwear additives, compared to a conventional lubricating composition not comprising a diester according to the invention.
La mise en œuvre d’un ou plusieurs diesters de formule (I) permet ainsi d’abaisser la teneur en additifs anti-usure conventionnels, et en particulier en additifs générateurs de cendres, de phosphore ou de soufre, tout en conservant d’excellentes performances en termes de propriétés anti-usure. L’abaissement de la teneur en additifs anti usure permet avantageusement de répondre aux spécifications des compositions lubrifiantes « LOW SAPS ». The use of one or more diesters of formula (I) thus makes it possible to lower the content of conventional anti-wear additives, and in particular in additives generating ash, phosphorus or sulfur, while retaining excellent performance in terms of anti-wear properties. The lowering of the content of antiwear additives advantageously makes it possible to meet the specifications of the "LOW SAPS" lubricating compositions.
D’autres caractéristiques, variantes et avantages de la mise en œuvre des diesters de formule (I), ressortiront mieux à la lecture de la description et des exemples qui vont suivre, donnés à titre illustratif et non limitatif de l’invention.
Dans la suite du texte, les expressions « compris entre ... et ... », « allant de ... à ... » et « variant de ... à ... » sont équivalentes et entendent signifier que les bornes sont incluses, sauf mention contraire. Other characteristics, variants and advantages of the use of the diesters of formula (I) will emerge more clearly on reading the description and the examples which follow, given by way of illustration and without limitation of the invention. In the remainder of the text, the expressions “between ... and ...”, “ranging from ... to ...” and “varying from ... to ...” are equivalent and are intended to mean that the terminals are included, unless otherwise stated.
DIESTER DE FORMULE fl) DIESTER OF FORMULA f)
Comme précisé précédemment, l’additif mis en œuvre selon l’invention est un diester ou mélange de diesters de formule générale (I) suivante : As previously specified, the additive used according to the invention is a diester or mixture of diesters of general formula (I) below:
Ra-C(0)-0-([C(R)2]n-0)s-C(0)-Rb (I) R a -C (0) -0 - ([C (R) 2 ] n -0) s -C (0) -R b (I)
dans laquelle : in which :
- R représentent, indépendamment les uns des autres, un atome d’hydrogène ou un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, notamment méthyle ; - R represent, independently of each other, a hydrogen atom or a (Ci-Cs) alkyl group, linear or branched, in particular a methyl, ethyl or propyl group, in particular methyl;
- s vaut 1 ou 2 ; - s is 1 or 2;
- n vaut 1 , 2 ou 3 ; en particulier n vaut 2 ou 3 et plus particulièrement n vaut 2, étant entendu que, lorsque s est différent de 1, n peuvent être identiques ou différents ; et - n is 1, 2 or 3; in particular n is 2 or 3 and more particularly n is 2, it being understood that, when s is different from 1, n may be the same or different; and
- Ra et Rb, identiques ou différents, représentent indépendamment les uns des autres, des groupements hydrocarbonés, saturés ou insaturés, linéaires ou ramifiés, présentant un enchaînement linéaire de 2 à 11 atomes de carbone, de préférence de 3 à 8 atomes de carbone ; - R a and R b , identical or different, represent, independently of one another, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear chain of 2 to 11 carbon atoms, preferably 3 to 8 carbon atoms carbon;
sous réserve que, lorsque s vaut 2 et n, identiques, valent 2, au moins l’un des groupe R représente un groupe (Ci-Cs)alkyle, linéaire ou ramifié ; et with the proviso that, when s is 2 and n, which are identical, are 2, at least one of the group R represents a (Ci-Cs) alkyl group, linear or branched; and
sous réserve que, lorsque s vaut 1 et n vaut 3, au moins l’un des groupes R lié au carbone en position bêta des atomes d’oxygène des fonctions esters représente un atome d’hydrogène. provided that, when s is 1 and n is 3, at least one of the groups R bonded to the carbon in beta position of the oxygen atoms of the ester functions represents a hydrogen atom.
Selon un mode de réalisation, Ra et Rb, identiques ou différents, représentent indépendamment les uns des autres, des groupements hydrocarbonés, saturés ou insaturés, linéaires ou ramifiés, comprenant de 2 à 11 atomes de carbone, de préférence de 3 à 8 atomes de carbone. According to one embodiment, R a and R b , identical or different, represent independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, comprising from 2 to 11 carbon atoms, preferably from 3 to 8 carbon atoms.
On désignera plus simplement dans la suite du texte, un diester de formule (I) mis en œuvre selon l’invention, par diester de l’invention. In the following text, a diester of formula (I) implemented according to the invention will be designated more simply by diester of the invention.
De préférence, dans le cadre de l’invention, on entend par :
- « Ct-z » où t et z sont des entiers, une chaîne carbonée pouvant avoir de t à z atomes de carbone ; par exemple Ci_4 une chaîne carbonée qui peut avoir de 1 à 4 atomes de carbone ; Preferably, in the context of the invention, the following definitions are understood: - "C tz " where t and z are integers, a carbon chain can have from t to z carbon atoms; for example Ci_ 4 a carbon chain which can have from 1 to 4 carbon atoms;
- « alkyle », un groupe aliphatique saturé, linéaire ou ramifié ; par exemple un groupe Ci-4-alkyle représente une chaîne carbonée de 1 à 4 atomes de carbone, linéaire ou ramifiée, plus particulièrement un méthyle, éthyle, propyle, isopropyle, butyle, isobutyle, fô/t-butylc. - "alkyl", a saturated, linear or branched aliphatic group; for example a Ci-4-alkyl group represents a carbon chain of 1 to 4 carbon atoms, linear or branched, more particularly methyl, ethyl, propyl, isopropyl, butyl, isobutyl, fo / t-butylc.
De préférence, dans la formule (I) précitée, lorsque s est différent de 1, tous les n sont identiques. Preferably, in the above formula (I), when s is different from 1, all n are identical.
En particulier, n dans la formule (I) précitée vaut 2 ou 3, et plus particulièrement n vaut 2. In particular, n in the above formula (I) is worth 2 or 3, and more particularly n is worth 2.
De préférence, au moins l’un des groupes R représente un groupe (Ci-Cs)alkyle, en particulier (Ci-C4)alkyle, linéaire ou ramifié, plus préférentiellement méthyle, éthyle ou propyle ; avantageusement méthyle. Preferably, at least one of the groups R represents a (Ci-Cs) alkyl group, in particular (Ci-C 4 ) alkyl, linear or branched, more preferably methyl, ethyl or propyl; advantageously methyl.
Selon un mode de réalisation particulièrement préféré, le diester de formule (I) mis en œuvre selon l’invention peut être plus particulièrement un diester de formule (F) suivante : According to a particularly preferred embodiment, the diester of formula (I) used according to the invention can more particularly be a diester of formula (F) below:
Ra-C(0)-0-([C(R)2]n-0)-([C(R’)2]m-0)s-i-C(0)-Rb (r) dans laquelle : R a -C (0) -0 - ([C (R) 2 ] n -0) - ([C (R ') 2 ] m -0) if -C (0) -R b (r) in which :
- R et R’ représentent, indépendamment les uns des autres, un atome d’hydrogène ou un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, notamment un groupe méthyle ; - R and R ’represent, independently of each other, a hydrogen atom or a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, in particular a methyl group;
- s vaut 1 ou 2 ; - s is 1 or 2;
- n vaut 2 ; - n is 2;
- m vaut 2 ; - m is 2;
- Ra et Rb, identiques ou différents, représentent indépendamment les uns des autres, des groupements hydrocarbonés, saturés ou insaturés, linéaires ou ramifiés, présentant un enchaînement linéaire de 2 à 11 atomes de carbone, de préférence de 3 à 8 atomes de carbone ;
sous réserve que, lorsque s vaut 2, au moins l’un des groupes R ou R’ représente un groupe (Ci-Cs)alkyle, linéaire ou ramifié. - R a and R b , identical or different, represent, independently of one another, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear chain of 2 to 11 carbon atoms, preferably 3 to 8 carbon atoms carbon; provided that, when s is 2, at least one of the groups R or R 'represents a (Ci-Cs) alkyl group, linear or branched.
De préférence, un diester mis en œuvre selon l’invention est de formule (F) dans laquelle au moins l’un des R ou R’ représente un groupe (Ci-Cs)alkyle, en particulier (Ci- C4)alkyle, linéaire ou ramifié, plus préférentiellement méthyle, éthyle ou propyle ; avantageusement méthyle. Preferably, a diester used according to the invention is of formula (F) in which at least one of the R or R ′ represents a (Ci-Cs) alkyl group, in particular (Ci-C 4 ) alkyl, linear or branched, more preferably methyl, ethyl or propyl; advantageously methyl.
Selon une variante de réalisation, s dans la formule (I) ou (F) précitée vaut 2. En particulier, le diester mis en œuvre selon l’invention peut être de formule (Fa) suivante : According to an alternative embodiment, s in the above formula (I) or (F) is equal to 2. In particular, the diester used according to the invention can be of the following formula (Fa):
Ra-C(0)-0-([C(R)2]n-0)-([C(R’)2]m-0)-C(0)-Rb R a -C (0) -0 - ([C (R) 2 ] n -0) - ([C (R ') 2 ] m -0) -C (0) -R b
(l’a) (the)
dans laquelle : in which :
- R et R’ représentent, indépendamment les uns des autres, un atome d’hydrogène ou un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, avantageusement méthyle ; - R and R ’represent, independently of each other, a hydrogen atom or a (Ci-Cs) alkyl group, linear or branched, in particular a methyl, ethyl or propyl group, advantageously methyl;
- n vaut 2 ; - n is 2;
- m vaut 2 ; - m is 2;
- Ra et Rb, identiques ou différents, représentent indépendamment les uns des autres, des groupements hydrocarbonés, saturés ou insaturés, linéaires ou ramifiés, présentant un enchaînement linéaire de 2 à 11 atomes de carbone, de préférence de 3 à 8 atomes de carbone ; - R a and R b , identical or different, represent independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear chain of 2 to 11 carbon atoms, preferably 3 to 8 atoms carbon;
sous réserve qu’au moins l’un des groupes R ou R’ représente un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier méthyle, éthyle ou propyle, avantageusement méthyle. with the proviso that at least one of the groups R or R ′ represents a (Ci-Cs) alkyl group, linear or branched, in particular methyl, ethyl or propyl, advantageously methyl.
De préférence, au moins l’un des groupes R représente un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, avantageusement méthyle ; et au moins l’un des R’ représente un groupe (Ci-Cs)alkylc, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, avantageusement méthyle. Preferably, at least one of the groups R represents a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl; and at least one of the R ’represents a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl.
Encore plus préférentiellement, le diester mis en œuvre selon l’invention peut être de formule (Fa) dans laquelle l’un des groupes R représente un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, avantageusement
méthyle ; et l’un des groupes R’ représente un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, avantageusement méthyle ; les autres groupes R et R’ représentant des atomes d’hydrogène. Even more preferably, the diester used according to the invention may be of formula (Fa) in which one of the groups R represents a (Ci-Cs) alkyl group, linear or branched, in particular a methyl, ethyl or propyle, advantageously methyl; and one of the groups R ′ represents a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl; the other groups R and R ′ representing hydrogen atoms.
Autrement dit, selon un mode de réalisation particulier, le diester mis en œuvre selon l’invention peut être de formule (I”a) suivante : In other words, according to a particular embodiment, the diester used according to the invention can have the following formula (I ”a):
Ra-C(0)-0-CHR1-CHR2-0-CHR3-CHR4-0-C(0)-Rb R a -C (0) -0-CHR 1 -CHR 2 -0-CHR 3 -CHR 4 -0-C (0) -R b
(I”a) (I ”a)
dans laquelle : in which :
- l’un des groupes R1 et R2 représente un groupe (Ci-Cs)alkyle, linéaire ou ramifié, l’autre représentant un atome d’hydrogène ; - one of the groups R 1 and R 2 represents a (Ci-Cs) alkyl group, linear or branched, the other representing a hydrogen atom;
- l’un des groupes R3 et R4 représente un groupe (Ci-Cs)alkyle, linéaire ou ramifié, l’autre représentant un atome d’hydrogène ; et - one of the groups R 3 and R 4 represents a (Ci-Cs) alkyl group, linear or branched, the other representing a hydrogen atom; and
- Ra et Rb, identiques ou différents, sont tels que définis précédemment. - R a and R b , identical or different, are as defined above.
En particulier, le diester mis en œuvre selon l’invention peut être de formule (I”a) dans laquelle : In particular, the diester used according to the invention can be of formula (I ”a) in which:
- l’un des groupes R1 et R2 représente un groupe méthyle, éthyle ou propyle, avantageusement méthyle, l’autre représentant un atome d’hydrogène ; et - one of the groups R 1 and R 2 represents a methyl, ethyl or propyl group, advantageously methyl, the other representing a hydrogen atom; and
- l’un des groupes R3 et R4 représente un groupe méthyle, éthyle ou propyle, avantageusement méthyle, l’autre représentant un atome d’hydrogène. one of the groups R 3 and R 4 represents a methyl, ethyl or propyl group, advantageously methyl, the other representing a hydrogen atom.
Selon une autre variante de réalisation, s dans la formule (I) ou (G) précitée vautAccording to another alternative embodiment, s in the above formula (I) or (G) is
1. 1.
Autrement dit, le diester mis en œuvre selon l’invention peut être de formule (F b) suivante : In other words, the diester used according to the invention can have the following formula (F b):
Ra-C(0)-0-([C(R)2]n-0)-C(0)-Rb R a -C (0) -0 - ([C (R) 2 ] n -0) -C (0) -R b
(I’b) (I’b)
dans laquelle : in which :
- R représentent, indépendamment les uns des autres, un atome d’hydrogène ou un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, avantageusement méthyle ; - R represent, independently of each other, a hydrogen atom or a (Ci-Cs) alkyl group, linear or branched, in particular a methyl, ethyl or propyl group, advantageously methyl;
- n vaut 2 ;
- Ra et Rb, identiques ou différents, représentent indépendamment les uns des autres, des groupements hydrocarbonés, saturés ou insaturés, linéaires ou ramifiés, présentant un enchaînement linéaire de 2 à 11 atomes de carbone, de préférence de 3 à 8 atomes de carbone. - n is 2; - R a and R b , identical or different, represent independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear chain of 2 to 11 carbon atoms, preferably 3 to 8 atoms carbon.
De préférence, dans la formule (I’b) précitée, au moins l’un des R représente un groupe (Ci-Cs)alkylc, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, avantageusement méthyle. Preferably, in the above formula (I’b), at least one of the R represents a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl.
En particulier, le diester mis en œuvre selon l’invention peut être de formule (I’b) dans laquelle un des groupes R représente un groupe (Ci-C5)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, avantageusement méthyle, les autres représentant des atomes d’hydrogène. In particular, the diester used according to the invention may be of formula (I'b) in which one of the groups R represents a (Ci-C5) alkyl group, linear or branched, in particular a methyl, ethyl or propyl group , advantageously methyl, the others representing hydrogen atoms.
Comme indiqué précédemment, Ra et Rb dans la formule (I), (F), (l’a), (I”a) ou (I’b) précitée, identiques ou différents, représentent des groupements hydrocarbonés, saturés ou insaturés, linéaires ou ramifiés, présentant un enchaînement linéaire de 2 à 11 atomes de carbone, de préférence de 3 à 8 atomes de carbone. As indicated above, R a and R b in formula (I), (F), (a), (I ”a) or (I'b) above, identical or different, represent hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear chain of 2 to 11 carbon atoms, preferably 3 to 8 carbon atoms.
On entend par groupement « hydrocarboné », tout groupement ayant un atome de carbone directement fixé au reste de la molécule et ayant principalement un caractère hydrocarboné aliphatique. The term “hydrocarbon” group is understood to mean any group having a carbon atom directly attached to the rest of the molecule and having mainly an aliphatic hydrocarbon character.
De préférence, Ra et Rb dans la formule (I), (F), (l’a), (I”a) ou (I’b) précitée, présentent un enchaînement linéaire de 3 à 6 atomes de carbone. Preferably, R a and R b in the formula (I), (F), (a), (I ”a) or (I'b) mentioned above, have a linear chain of 3 to 6 carbon atoms.
Selon une variante de réalisation, Ra et Rb dans la formule (I), (F), (l’a), (I”a) ou (I’b) précitée, présentent un enchaînement linéaire de 8 à 11 atomes de carbone. According to an alternative embodiment, R a and R b in formula (I), (F), (a), (I ”a) or (I'b) above, have a linear sequence of 8 to 11 atoms of carbon.
Par « enchaînement linéaire de t à z atomes de carbone », on entend une chaîne carbonée saturée ou insaturée, de préférence saturée, comprenant de t à z atomes de carbone les uns à la suite des autres, les atomes de carbone présents éventuellement au niveau des ramifications de la chaîne carbonée n’étant pas pris en compte dans le nombre d’atomes de carbone (t-z) constituant l’enchaînement linéaire. By “linear chain from t to z carbon atoms” is meant a saturated or unsaturated carbon chain, preferably saturated, comprising from t to z carbon atoms one after the other, the carbon atoms possibly present at the level ramifications of the carbon chain not being taken into account in the number of carbon atoms (tz) constituting the linear chain.
Selon un mode de réalisation particulier, dans la formule (I), (F), (l’a), (I”a) ou (I’b) précitée, Ra et Rb, identiques ou différents, sont issus d’origine végétale, animale ou pétrolière.
Selon un mode de réalisation particulier, dans la formule (I), (G), (l’a), (I”a) ou (I’b) précitée, Ra et Rb, identiques ou différents, représentent des groupements saturés. According to a particular embodiment, in formula (I), (F), (a), (I ”a) or (I'b) above, R a and R b , identical or different, are derived from vegetable, animal or petroleum origin. According to a particular embodiment, in formula (I), (G), (a), (I ”a) or (I'b) above, R a and R b , identical or different, represent groups saturated.
Selon un autre mode de réalisation particulièrement préféré, dans la formule (I), (F), (Fa), (I”a) ou (I’b) précitée, Ra et Rb, identiques ou différents, représentent des groupements linéaires. According to another particularly preferred embodiment, in formula (I), (F), (Fa), (I ”a) or (I'b) above, R a and R b , identical or different, represent groups linear.
Selon un autre mode de réalisation particulier, dans la formule (I), (F), (l’a), (I”a) ou (I’b) précitée, Ra et Rb représentent des groupements hydrocarbonés linéaires saturés en CH à CI I , en particulier en Cs à Cio. According to another particular embodiment, in formula (I), (F), (a), (I ”a) or (I'b) above, R a and R b represent linear hydrocarbon groups saturated in C H to C II , in particular Cs to Cio.
En particulier, Ra et Rb sont identiques. In particular, R a and R b are identical.
De préférence, Ra et Rb représentent tous les deux des groupements «-octylc ou «-undécylc, de préférence «-octylc. Preferably, R a and R b both represent groups "-octylc or" -undécylc, preferably "-octylc.
Selon un autre mode de réalisation particulier, dans la formule (I), (F), (l’a), (I”a) ou (I’b) précitée, Ra et Rb représentent des groupements hydrocarbonés ramifiés comprenant de 2 à 11 atomes de carbone, de préférence de 3 à 8 atomes de carbone. According to another particular embodiment, in formula (I), (F), (a), (I ”a) or (I'b) above, R a and R b represent branched hydrocarbon groups comprising 2 to 11 carbon atoms, preferably 3 to 8 carbon atoms.
Les diesters de formule (I) mis en œuvre selon l’invention peuvent être disponibles dans le commerce ou préparés selon des méthodes de synthèse décrites dans la littérature et connues de l’homme du métier. Ces méthodes de synthèse mettent plus particulièrement en œuvre une réaction d’estérification entre un composé diol de formule H0-([C(R)2]n-0)s-0H et des composés de formule Ra-COOH et Rb-COOH, avec Ra et Rb, identiques ou différents, étant tels que définis précédemment. The diesters of formula (I) used according to the invention may be commercially available or prepared according to synthesis methods described in the literature and known to those skilled in the art. These synthetic methods more particularly implement an esterification reaction between a diol compound of formula H0 - ([[C (R) 2 ] n -0) s -0H and compounds of formula R a -COOH and R b - COOH, with R a and R b , identical or different, being as defined above.
Bien entendu, il appartient à l’homme du métier d’ajuster les conditions de synthèse pour obtenir les diesters requis selon l’invention. Of course, it is up to the person skilled in the art to adjust the synthesis conditions in order to obtain the diesters required according to the invention.
A titre d’exemples, des diesters de formule (I) précitée, en particulier de formule (F) précitée, peuvent être obtenus par réaction d’estérification entre un mono- ou poly- propylène glycol, en particulier le monopropylène glycol (MPG) ou le dipropylène glycol (DPG), et un ou plusieurs acides carboxyliques Ra-COOH et Rb-COOH adéquats. By way of examples, diesters of the above formula (I), in particular of the above formula (F), can be obtained by esterification reaction between a mono- or polypropylene glycol, in particular monopropylene glycol (MPG) or dipropylene glycol (DPG), and one or more suitable carboxylic acids R a -COOH and R b -COOH.
A titre d’exemple, un diester ou mélange de diesters de formule (F) telle que définie précédemment, où : By way of example, a diester or mixture of diesters of formula (F) as defined above, where:
- s vaut 2,
- l’un des groupes R représentant un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, avantageusement méthyle, les autres représentant des atomes d’hydrogène ; et - s is 2, one of the groups R representing a (Ci-Cs) alkyl group, linear or branched, in particular a methyl, ethyl or propyl group, advantageously methyl, the others representing hydrogen atoms; and
- l’un des groupes R’ représentant un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, avantageusement méthyle, les autres représentant des atomes d’hydrogène, one of the groups R ’representing a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl, the others representing hydrogen atoms,
peut être obtenu via une réaction d’estérification entre le dipropylène glycol (DPG) et un ou plusieurs acides carboxyliques Ra-COOH et Rb-COOH adéquats. can be obtained via an esterification reaction between dipropylene glycol (DPG) and one or more suitable carboxylic acids R a -COOH and R b -COOH.
Un diester de formule (F) telle que définie précédemment, où A diester of formula (F) as defined above, where
- s vaut 1 , - s is 1,
- l’un des groupes R représentant un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, avantageusement méthyle, les autres représentant des atomes d’hydrogène, one of the groups R representing a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl, the others representing hydrogen atoms,
peut être obtenu via une réaction d’estérification entre le monopropylène glycol (MPG) et un ou plusieurs acides carboxyliques Ra-COOH et Rb-COOH adéquats. can be obtained via an esterification reaction between monopropylene glycol (MPG) and one or more suitable carboxylic acids R a -COOH and R b -COOH.
En particulier, dans le cas où Ra et Rb représentent tous les deux des groupements «-octylc ou «-undécylc, un tel diester ou mélange de diesters peut être ainsi obtenu par réaction d’estérification entre le monopropylène glycol ou dipropylène glycol et l’acide nonanoïque ou l’acide dodécanoïque. In particular, in the case where R a and R b both represent “-octylc” or “-undecylc” groups, such a diester or mixture of diesters can thus be obtained by esterification reaction between monopropylene glycol or dipropylene glycol and nonanoic acid or dodecanoic acid.
Il est entendu dans le cadre de la présente invention que le diester de formule (I) telle que définie précédemment peut être sous forme d’un mélange de diesters de formule (I) telle que définie précédemment. It is understood in the context of the present invention that the diester of formula (I) as defined above may be in the form of a mixture of diesters of formula (I) as defined above.
APPLICATION DANS UNE COMPOSITION LUBRIFIANTE APPLICATION IN A LUBRICATING COMPOSITION
Les diesters de formule (I) sont mis en œuvre à titre d’additifs dans une composition lubrifiante, en particulier dans une composition lubrifiante pour moteur, en particulier de véhicule, et plus préférentiellement pour moteur de véhicule automobile. The diesters of formula (I) are used as additives in a lubricating composition, in particular in a lubricating composition for an engine, in particular for a vehicle, and more preferably for a motor vehicle engine.
D’une manière générale, le ou lesdits diesters de formule (I) peuvent être mis en œuvre dans une composition lubrifiante, à raison de 1 % à 30 % en poids, en particulier de 5 % à 30 % à poids, notamment de 5 % à 25 % en poids, de préférence de 5 % à 20 % en poids, par rapport au poids total de la composition lubrifiante.
Additifs anti-usure In general, the said diesters or diesters of formula (I) can be used in a lubricating composition, in a proportion of 1% to 30% by weight, in particular from 5% to 30% by weight, in particular from 5 % to 25% by weight, preferably from 5% to 20% by weight, relative to the total weight of the lubricating composition. Anti-wear additives
Comme indiqué précédemment, une composition lubrifiante considérée selon l’invention comprend un ou plusieurs additifs anti-usure conventionnels. As indicated above, a lubricating composition considered according to the invention comprises one or more conventional anti-wear additives.
Par « additif anti-usure », on entend désigner un composé qui, mis en œuvre dans une composition lubrifiante, notamment une composition lubrifiante pour moteur de véhicule, en particulier pour moteur de véhicule automobile, permet d’améliorer les propriétés anti-usure de la composition. The term “anti-wear additive” is intended to denote a compound which, used in a lubricating composition, in particular a lubricating composition for a vehicle engine, in particular for a motor vehicle engine, makes it possible to improve the anti-wear properties of the composition.
Il existe une grande variété d’additifs anti-usure, comme par exemple des additifs polysulfures, des additifs oléfïnes soufrées ou encore les additifs phospho-soufrés comme les alkylthiophosphates métalliques, en particulier les alkylthiophosphates de zinc, et plus spécifiquement les dialkyldithiophosphates de zinc ou ZnDTP. Les composés préférés sont de formule Zn((SP(S)(OR)(OR’))2, dans laquelle R et R’, identiques ou différents, représentent, indépendamment les uns des autres, des groupements alkyles, linéaires ou ramifiés, de préférence ramifiés, comportant préférentiellement de 1 à 18 atomes de carbone. De préférence, au moins l’un des groupements R et R’ représente un groupement alkyle, de préférence ramifié, présentant au moins 6 atomes de carbone, en particulier ayant de 6 à 18 atomes de carbone. There are a wide variety of anti-wear additives, such as for example polysulphide additives, sulfur olefin additives or phospho-sulfur 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) (OR ')) 2 , in which R and R', identical or different, represent, independently of one another, alkyl groups, linear or branched, preferably branched, preferably comprising from 1 to 18 carbon atoms, preferably at least one of the groups R and R ′ represents an alkyl group, preferably branched, having at least 6 carbon atoms, in particular having 6 to 18 carbon atoms.
Ainsi, selon un mode de réalisation particulier, le ou les diesters de formule (I) selon l’invention sont mis en œuvre dans une composition lubrifiante en combinaison avec un ou plusieurs additifs de type dialkyldithiophosphate de zinc, en particulier de formule Zn((SP(S)(OR)(OR’)) précitée. Thus, according to a particular embodiment, the diesters of formula (I) according to the invention are used in a lubricating composition in combination with one or more additives of the zinc dialkyldithiophosphate type, in particular of formula Zn (( SP (S) (OR) (OR ')) above.
Une composition lubrifiante considérée selon l’invention peut comprendre de 0,01 à 6 % en poids, préférentiellement de 0,05 à 4 % en poids, plus préférentiellement de 0,1 à 2 % en poids, par rapport au poids total de la composition, d’additifs anti-usure. A lubricating composition considered according to the invention may comprise from 0.01 to 6% by weight, preferably from 0.05 to 4% by weight, more preferably from 0.1 to 2% by weight, relative to the total weight of the composition, anti-wear additives.
Comme évoqué précédemment, la mise en œuvre d’un ou plusieurs diesters de formule (I) selon l’invention permet avantageusement d’améliorer les propriétés anti-usure de la composition lubrifiante. Il en résulte selon l’invention la possibilité d’obtenir une composition lubrifiante présentant d’excellentes propriétés anti-usure, tout en abaissant la teneur en additifs anti-usure classiquement utilisés. As mentioned above, the use of one or more diesters of formula (I) according to the invention advantageously makes it possible to improve the anti-wear properties of the lubricating composition. According to the invention, this results in the possibility of obtaining a lubricating composition having excellent anti-wear properties, while lowering the content of conventionally used anti-wear additives.
Ainsi, selon une variante de réalisation particulièrement avantageuse, le ou les additif(s) anti-usure, en particulier générateurs de soufre ou de phosphore, sont présents dans
une composition lubrifiante en une teneur inférieure ou égale à 2 % en poids, en particulier inférieure ou égale à 1 % en poids. Thus, according to a particularly advantageous alternative embodiment, the anti-wear additive (s), in particular sulfur or phosphorus generators, are present in a lubricating composition in a content less than or equal to 2% by weight, in particular less than or equal to 1% by weight.
Plus particulièrement, de manière avantageuse, il est possible d’abaisser la teneur en additifs anti-usure classiques, tels que des dialkyldithiophosphates de zinc, pour répondre aux spécifications « LOW SAPS » recherchées pour la composition lubrifiante. More particularly, advantageously, it is possible to lower the content of conventional antiwear additives, such as zinc dialkyldithiophosphates, to meet the "LOW SAPS" specifications sought for the lubricant composition.
Une composition lubrifiante comprend typiquement, outre un ou plusieurs diesters de formule (I) tels que définis précédemment, en combinaison avec un ou plusieurs additifs anti-usure conventionnels, une ou plusieurs huiles de base, ainsi que d’autres additifs, classiquement considérés dans les compositions lubrifiantes. A lubricating composition typically comprises, in addition to one or more diesters of formula (I) as defined above, in combination with one or more conventional anti-wear additives, one or more base oils, as well as other additives, conventionally considered in lubricating compositions.
En termes de formulation d’une telle composition lubrifiante, le ou les diesters de formule (I) peuvent être additionnés à une huile ou mélange d’huiles de base, puis les autres additifs complémentaires, y compris le ou les additifs anti-usure, ajoutés. In terms of the formulation of such a lubricating composition, the diester (s) of formula (I) can be added to an oil or mixture of base oils, then the other additional additives, including the anti-wear additive (s), added.
Alternativement, le ou lesdits esters de formule (I) peuvent être additionnés à une formulation lubrifiante conventionnelle préexistante, comprenant notamment une ou plusieurs huiles de base et des additifs complémentaires, en particulier un ou plusieurs additifs anti-usure. Alternatively, the said ester (s) of formula (I) can be added to a conventional pre-existing lubricant formulation, comprising in particular one or more base oils and additional additives, in particular one or more anti-wear additives.
Par exemple, une composition lubrifiante pour moteur peut être supplémentée avec un ou plusieurs diesters de formule (I) conformes à l’invention en ajoutant, par exemple, le ou lesdits diesters directement au sein du réservoir préalablement rempli avec une formulation classique de lubrifiant. For example, a lubricant composition for an engine can be supplemented with one or more diesters of formula (I) in accordance with the invention by adding, for example, the said diester (s) directly to the reservoir previously filled with a conventional formulation of lubricant.
Huiles de base Base oils
Une composition lubrifiante considérée selon l’invention peut ainsi comprendre en outre une ou plusieurs huiles de base distinctes des diesters de formule (I). A lubricating composition considered according to the invention can thus also comprise one or more base oils distinct from the diesters of formula (I).
Ces huiles de base peuvent être choisies parmi les huiles de base conventionnellement utilisées dans le domaine des huiles lubrifiantes, telles que les huiles minérales, synthétiques ou naturelles, animales ou végétales ou leurs mélanges. These base oils can be chosen from the base oils conventionally used in the field of lubricating oils, such as mineral, synthetic or natural, animal or vegetable oils or their mixtures.
Il peut s’agir d’un mélange de plusieurs huiles de base, par exemple un mélange de deux, trois, ou quatre huiles de base. It can be a mixture of several base oils, for example a mixture of two, three, or four base oils.
Les huiles de base des compositions lubrifiantes considérées selon l’invention peuvent être en particulier des huiles d’origines minérales ou synthétiques appartenant aux
groupes I à V selon les classes définies dans la classification API (ou leurs équivalents selon la classification ATIEL) et présentées dans le tableau A ci-dessous ou leurs mélanges, pour autant qu’elles soient distinctes des diesters de l’invention. The base oils of the lubricating compositions considered according to the invention may in particular be oils of mineral or synthetic origins belonging to the groups I to V according to the classes defined in the API classification (or their equivalents according to the ATIEL classification) and presented in table A below or their mixtures, provided that they are distinct from the diesters of the invention.
Tableau A Table A
Les huiles de base minérales incluent tous types d’huiles de base obtenues par distillation atmosphérique et sous vide du pétrole brut, suivies d’opérations de raffinage telles qu’ extraction au solvant, désalphatage, déparaffinage au solvant, hydrotraitement, hydrocraquage, hydroisomérisation et hydro finition. Mineral base oils 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, hydrotreating, hydrocracking, hydroisomerization and hydro finish.
Les huiles de base synthétiques peuvent être des esters d’acides carboxyliques et d’alcools, des polyalphaoléfines ou encore des polyalkylène glycol (PAG) obtenus par polymérisation ou copolymérisation d’oxydes d’alkylène comprenant de 2 à 8 atomes de carbone, en particulier de 2 à 4 atomes de carbone. Les polyalphaoléfines utilisées comme huiles de base sont par exemple obtenues à partir de monomères comprenant 4 à 32 atomes de carbone, par exemple à partir de décène, d’octène ou de dodécène, et dont la viscosité à l00°C est comprise entre 1,5 et 15 mm2. s 1 selon la norme ASTM D445. Leur masse moléculaire moyenne est généralement comprise entre 250 et 3000 selon la norme ASTM D5296. The synthetic base oils can be esters of carboxylic acids and alcohols, polyalphaolefins or else polyalkylene glycol (PAG) obtained by polymerization or copolymerization of alkylene oxides comprising from 2 to 8 carbon atoms, in particular from 2 to 4 carbon atoms. The polyalphaolefins used as base oils are for example obtained from monomers comprising 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 standard ASTM D445. Their average molecular weight is generally between 250 and 3000 according to standard ASTM D5296.
Des mélanges d’huiles synthétiques et minérales, pouvant être biosourcées, peuvent également être employés.
Il n’existe généralement aucune limitation quant à l’emploi d’huiles de base différentes dans la composition lubrifiante, si ce n’est qu’elles doivent avoir des propriétés, notamment de viscosité, d’indice de viscosité, de teneur en soufre ou de résistance à l’oxydation, adaptées à une utilisation pour des moteurs de véhicule. Mixtures of synthetic and mineral oils, which can be bio-sourced, can also be used. There is generally no limitation as to the use of different base oils in the lubricating composition, except that they must have properties, in particular viscosity, viscosity index, sulfur content. or resistance to oxidation, suitable for use in vehicle engines.
De préférence, une composition lubrifiante considérée selon l’invention comprend au moins une huile de base choisie parmi les huiles de groupe II, III et IV de la classification API, et leurs mélanges. Preferably, a lubricating composition considered according to the invention comprises at least one base oil chosen from group II, III and IV oils of the API classification, and their mixtures.
En particulier, une telle composition lubrifiante peut comprendre au moins une huile de base de groupe III. In particular, such a lubricating composition can comprise at least one group III base oil.
Une composition lubrifiante considérée selon l’invention peut comprendre au moins 50 % en poids d’huile(s) de base par rapport à son poids total, en particulier au moins 60 % en poids d’huile(s) de base, et plus particulièrement entre 60 et 99 % en poids d’huile(s) de base. A lubricating composition considered according to the invention may comprise at least 50% by weight of base oil (s) relative to its total weight, in particular at least 60% by weight of base oil (s), and more particularly between 60 and 99% by weight of base oil (s).
De préférence, l’huile ou les huiles de groupe III représente(nt) au moins 50 % en poids, en particulier au moins 60 % en poids du poids total des huiles de base de la composition. Preferably, the group III oil or oils represent (s) at least 50% by weight, in particular at least 60% by weight of the total weight of the base oils of the composition.
Autres additifs Other additives
Une composition lubrifiante considérée selon l’invention peut également comprendre en outre tous types d’additifs, adaptés à une utilisation dans un lubrifiant pour moteur de véhicule, en particulier de véhicule automobile. A lubricant composition considered according to the invention may also further comprise all types of additives, suitable for use in a lubricant for a vehicle engine, in particular for a motor vehicle.
Ces additifs peuvent être introduits isolément et/ou sous la forme d’un mélange à l’image de ceux déjà disponibles à la vente pour les formulations de lubrifiants commerciaux pour moteurs de véhicules, de niveau de performance tels que définis par l’ACEA (Association des Constructeurs Européens d’ Automobiles) et/ou l’API (American Petroleum Institute), bien connus de l’homme du métier. These additives can be introduced in isolation and / or in the form of a mixture like those already available for sale for formulations of commercial lubricants for vehicle engines, with performance levels as defined by ACEA ( Association of European Automobile Manufacturers) and / or API (American Petroleum Institute), well known to those skilled in the art.
Ces additifs peuvent notamment être choisis parmi les additifs modificateurs de frottement, les additifs extrême pression, les additifs détergents, les additifs antioxydants, les améliorants de l’indice de viscosité (VI), les additifs abaisseurs du point d’écoulement (PPD), les agents dispersants, les agents anti-mousse, les épaississants, et leurs mélanges.
Une composition lubrifiante considérée selon l’invention peut comprendre au moins un additif modificateur de frottement. These additives can in particular be chosen from friction modifying additives, extreme pressure additives, detergent additives, antioxidant additives, viscosity index improvers (VI), pour point lowering additives (PPD), dispersing agents, anti-foaming agents, thickeners, and mixtures thereof. A lubricating composition considered according to the invention may comprise at least one friction-modifying additive.
Les additifs modificateurs de frottement peuvent être choisis parmi des composés apportant des éléments métalliques et des composés exempts de cendres. The friction modifying additives can be chosen from compounds providing metallic elements and ash-free compounds.
Parmi les composés apportant des éléments métalliques, on peut citer les complexes de métaux de transition tels que Mo, Sb. Sn, Fe, Cu, Zn dont les ligands peuvent être des composés hydrocarbonés comprenant des atomes d’oxygène, d’azote, de soufre ou de phosphore. Among the compounds providing metallic elements, mention may be made of transition metal complexes such as Mo, Sb. Sn, Fe, Cu, Zn, the ligands of which can be hydrocarbon compounds comprising oxygen, nitrogen, sulfur or phosphorus atoms.
Les additifs modificateurs de frottement exempts de cendres sont généralement d’origine organique et peuvent être choisis parmi les monoesters d’acides gras et de polyols, les amines alcoxylées, les amines grasses alcoxylées, les époxydes gras, les époxydes gras de borate, les amines grasses ou les esters de glycérol d’acide gras. Selon l’invention, les composés gras comprennent au moins un groupement hydrocarboné comprenant de 10 à 24 atomes de carbone. The ash-free friction-modifying additives are generally of organic origin and can be chosen from monoesters of fatty acids and of polyols, alkoxylated amines, alkoxylated fatty amines, fatty epoxides, fatty borate epoxides, amines fatty or fatty acid glycerol esters. According to the invention, the fatty compounds comprise at least one hydrocarbon group comprising from 10 to 24 carbon atoms.
Selon une variante avantageuse, une composition lubrifiante comprend au moins un additif modificateur de frottement, en particulier à base de molybdène. According to an advantageous variant, a lubricating composition comprises at least one friction-modifying additive, in particular based on molybdenum.
En particulier, les composés à base de molybdène peuvent être choisis parmi les dithiocarbamates de molybdène (Mo-DTC), les dithiophosphates de molybdène (Mo-DTP), et leurs mélanges. In particular, the molybdenum-based compounds can be chosen from molybdenum dithiocarbamates (Mo-DTC), molybdenum dithiophosphates (Mo-DTP), and their mixtures.
Selon un mode de réalisation particulier, une composition lubrifiante comprend au moins un composé Mo-DTC et au moins un composé Mo-DTP. Une composition lubrifiante peut notamment comprendre une teneur en molybdène comprise entre 1000 et 2500 ppm. According to a particular embodiment, a lubricating composition comprises at least one Mo-DTC compound and at least one Mo-DTP compound. A lubricating composition can in particular comprise a molybdenum content of between 1000 and 2500 ppm.
De manière avantageuse, une telle composition permet d’effectuer des économies de carburant supplémentaires. Advantageously, such a composition makes it possible to make additional fuel savings.
De manière avantageuse, une composition lubrifiante considérée selon l’invention peut comprendre de 0,01 à 5 % en poids, de préférence de 0,01 à 5 % en poids, plus particulièrement de 0,1 à 2 % en poids ou encore plus particulièrement de 0,1 à 1,5 % en poids, par rapport au poids total de la composition lubrifiante, d’additifs modificateurs de frottement, incluant avantageusement au moins un additif modificateur de frottement à base de molybdène.
Une composition lubrifiante considérée selon l’invention peut comprendre au moins un additif antioxydant. Les additifs antioxydants sont pour l’essentiel dédiés à retarder la dégradation de la composition lubrifiante en service. Cette dégradation peut notamment se traduire par la formation de dépôts, par la présence de boues ou par une augmentation de la viscosité de la composition lubrifiante. Ils agissent notamment comme inhibiteurs radicalaires ou destructeurs d’hydroperoxydes. Advantageously, a lubricating composition considered according to the invention can comprise from 0.01 to 5% by weight, preferably from 0.01 to 5% by weight, more particularly from 0.1 to 2% by weight or even more particularly from 0.1 to 1.5% by weight, relative to the total weight of the lubricating composition, of friction-modifying additives, advantageously including at least one friction-modifying additive based on molybdenum. A lubricating composition considered according to the invention can comprise at least one antioxidant additive. Antioxidant additives are essentially dedicated to delaying the degradation of the lubricating composition in service. This degradation can in particular be reflected by the formation of deposits, by the presence of sludge or by an increase in the viscosity of the lubricating composition. They act in particular as radical inhibitors or destroyers of hydroperoxides.
Parmi les additifs antioxydants couramment employés on peut citer les antioxydants de type phénolique, las additifs antioxydant de type aminé, les additifs antioxydants phosphosoufrés. Certains de ces additifs antioxydants, par exemple les additifs antioxydants phosphosoufrés, peuvent être générateurs de cendres. Les additifs antioxydants phénoliques peuvent être exempts de cendres ou bien être sous forme de sels métalliques neutres ou basiques. Les additifs antioxydants peuvent notamment être choisis parmi les phénols stériquement encombrés, les esters de phénol stériquement encombrés et les phénols stériquement encombrés comprenant un pont thioéther, les diphény lamines, les diphénylamines substituées par au moins un groupement alkyle en C1-C12, les N,N’-dialkyle- aryle-diamines et leurs mélanges. Among the antioxidant additives commonly used there may be mentioned antioxidants of the phenolic type, the antioxidant additives of the amino type, the phosphosulfurized antioxidant additives. Some of these antioxidant additives, for example phosphosulfur antioxidant additives, can generate ash. The phenolic antioxidant additives may be ash-free or may 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, dipheny lamines, diphenylamines substituted by at least one C1-C12 alkyl group, N, N'-dialkyl-aryl-diamines and mixtures thereof.
De préférence, les phénols stériquement encombrés sont choisis parmi les composés comprenant un groupement phénol dont au moins un carbone vicinal du carbone portant la fonction alcool est substitué par au moins un groupement alkyle en C1-C10, de préférence un groupement alkyle en Ci -CY,, de préférence un groupement alkyle en C4, de préférence par le groupement ter-butyle. Preferably, the sterically hindered phenols are chosen from compounds comprising a phenol group in which at least one vicinal carbon of the carbon carrying the alcohol function is substituted by at least one C 1 -C 10 alkyl group, preferably a C 1 -C 6 alkyl group. ,, preferably a C 4 alkyl group, preferably by the ter-butyl group.
Les composés aminés sont une autre classe d’additifs antioxydants pouvant être utilisés, éventuellement en combinaison avec les additifs antioxydants phénoliques. Des exemples de composés aminés sont les amines aromatiques, par exemple les amines aromatiques de formule NR5R6R7 dans laquelle R5 représente un groupement aliphatique ou un groupement aromatique, éventuellement substitué, R6 représente un groupement aromatique, éventuellement substitué, R7 représente un atome d’hydrogène, un groupement alkyle, un groupement aryle ou un groupement de formule R8S(0)zR9 dans laquelle R8 représente un groupement alkylène ou un groupement alkenylène, R9 représente un groupement alkyle, un groupement alcényle ou un groupement aryle et z représente 0, 1 ou 2.
Des alkyl phénols sulfurisés ou leurs sels de métaux alcalins et alcalino-terreux peuvent également être utilisés comme additifs antioxydants. Amino compounds are another class of antioxidant additives that can be used, possibly in combination with phenolic antioxidant additives. Examples of amino compounds are the aromatic amines, for example the aromatic amines of formula NR 5 R 6 R 7 in which R 5 represents an aliphatic group or an aromatic group, optionally substituted, R 6 represents an aromatic group, optionally substituted, R 7 represents a hydrogen atom, an alkyl group, an aryl group or a group of formula R 8 S (0) z R 9 in which R 8 represents an alkylene group or an alkenylene group, R 9 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.
Une composition lubrifiante considérée selon l’invention peut contenir tous types d’additifs antioxydants connus de l’homme du métier. De manière avantageuse, la composition lubrifiante comprend au moins un additif antioxydant exempt de cendres. A lubricating composition considered according to the invention can contain all types of antioxidant additives known to the skilled person. Advantageously, the lubricating composition comprises at least one antioxidant additive free from ash.
De manière également avantageuse, une composition lubrifiante considérée selon l’invention peut comprendre de 0,1 à 2 % en poids, par rapport au poids total de la composition, d’au moins un additif antioxydant. Also advantageously, a lubricating composition considered according to the invention may comprise from 0.1 to 2% by weight, relative to the total weight of the composition, of at least one antioxidant additive.
Une composition lubrifiante considérée selon l’invention peut comprendre au moins un additif détergent. Les additifs dits détergents permettent généralement de réduire la formation de dépôts à la surface des pièces métalliques par dissolution des produits secondaires d’oxydation et de combustion. A lubricating composition considered according to the invention may comprise at least one detergent additive. So-called detergent additives generally reduce the formation of deposits on the surface of metal parts by dissolving secondary oxidation and combustion products.
Les additifs détergents sont généralement connus de l’homme de métier. Les additifs détergents peuvent être des composés anioniques comprenant une longue chaîne hydrocarbonée lipophile et une tête hydrophile. Le cation associé peut être un cation métallique d’un métal alcalin ou alcalinoterreux. Detergent additives 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 metal cation of an alkali or alkaline earth metal.
Les additifs détergents sont préférentiellement choisis parmi les sels de métaux alcalins ou de métaux alcalino-terreux d’acides carboxyliques, les sulfonates, les salicylates, les naphténates, ainsi que les sels de phénates. Les métaux alcalins et alcalino-terreux sont préférentiellement le calcium, le magnésium, le sodium ou le baryum. Ces sels métalliques comprennent généralement le métal en quantité stœchiométrique ou bien en excès, donc en quantité supérieure à la quantité stœchiométrique. Il s’agit alors d’additifs détergents surbasés ; le métal en excès apportant le caractère surbasé à l’additif détergent est alors généralement sous la forme d’un sel métallique insoluble dans l’huile de base, par exemple un carbonate, un hydroxyde, un oxalate, un acétate, un glutamate, préférentiellement un carbonate. The detergent additives are preferably chosen from the alkali metal or alkaline earth metal salts of carboxylic acids, the sulfonates, the salicylates, the naphthenates, as well as the phenate salts. The alkali and alkaline earth metals are preferably calcium, magnesium, sodium or barium. These metal salts generally include the metal in a stoichiometric amount or in excess, therefore in an amount greater than the stoichiometric amount. These are overbased detergent additives; the excess metal bringing the overbased character to the detergent additive is then generally in the form of a metal salt insoluble in the base oil, for example a carbonate, a hydroxide, an oxalate, an acetate, a glutamate, preferably a carbonate.
Les additifs détergent sont généralement mis en œuvre en une teneur allant de 0,5 à 8 %, de préférence de 0,5 à 4 % en poids, par rapport au poids total de la composition lubrifiante. Avantageusement, ils sont présents en une teneur inférieure à 4 % en poids, en particulier inférieure à 2 % en poids, notamment inférieure à 1 % en poids, voire la composition lubrifiante est exempte d’additif(s) détergent.
Une composition lubrifiante considérée selon l’invention peut comprendre au moins un additif abaisseur de point d’écoulement (dits encore agents « PPD » pour « Pour Point Depressant » en langue anglaise). En ralentissant la formation de cristaux de paraffine, les additifs abaisseurs de point d’écoulement améliorent généralement le comportement à froid de la composition lubrifiante. The detergent additives are generally used in a content ranging from 0.5 to 8%, preferably from 0.5 to 4% by weight, relative to the total weight of the lubricating composition. Advantageously, they are present in a content of less than 4% by weight, in particular less than 2% by weight, in particular less than 1% by weight, or even the lubricating composition is free from detergent additive (s). A lubricant composition considered according to the invention may comprise at least one pour point depressant additive (also called "PPD" agents for "Pour Point Depressant" in English). By slowing the formation of paraffin crystals, pour point lowering additives generally improve the cold behavior of the lubricant composition.
Comme exemple d’agents de réduction du point d’écoulement, on peut citer les polyméthacrylates d’alkyle, les polyacrylates, les polyarylamides, les polyalkylphénols, les polyalkylnaphtalènes et les polystyrènes alkylés. Examples of pour point reducing agents include polyalkyl methacrylates, polyacrylates, polyarylamides, polyalkylphenols, polyalkylnaphthalenes and alkylated polystyrenes.
Une composition lubrifiante considérée selon l’invention peut également comprendre au moins un agent dispersant. Les agents dispersants assurent le maintien en suspension et l’évacuation des contaminants solides insolubles constitués par les produits secondaires d’oxydation qui se forment lorsque la composition lubrifiante est en service. Ils peuvent être choisis parmi les bases de Mannich, les succinimides et leurs dérivés. A lubricating composition considered according to the invention can also comprise at least one dispersing agent. The dispersing agents ensure the suspension and the evacuation of the insoluble solid contaminants constituted by the secondary oxidation products which are formed when the lubricating composition is in use. They can be chosen from Mannich bases, succinimides and their derivatives.
En particulier, une composition lubrifiante considérée selon l’invention peut comprendre de 0,2 à 10 % en poids d’agent(s) dispersant(s), par rapport au poids total de la composition. In particular, a lubricating composition considered according to the invention can comprise from 0.2 to 10% by weight of dispersing agent (s), relative to the total weight of the composition.
Une composition lubrifiante considérée selon l’invention peut également comprendre au moins un améliorant de l’indice de viscosité (VI). Les améliorants de l’indice de viscosité (VI), en particulier les polymères améliorant l’indice de viscosité, permettent de garantir une bonne tenue à froid et une viscosité minimale à haute température. Comme exemples de polymère améliorant l’indice de viscosité, on peut citer les esters polymères, les homopolymères ou les copolymères, hydrogénés ou non-hydrogénés du styrène, du butadiène et de l’isoprène, les homopolymères ou les copolymères d’oléfïne, telle que l’éthylène ou le propylène, les polyacrylates et polyméthacrylates (PMA). A lubricant composition considered according to the invention can also comprise at least one viscosity index (VI) improver. The viscosity index improvers (VI), in particular the viscosity index improving polymers, make it possible to guarantee good resistance to cold and minimum viscosity at high temperature. As examples of polymer improving the viscosity index, mention may be made of polymeric esters, homopolymers or copolymers, hydrogenated or non-hydrogenated of styrene, butadiene and isoprene, homopolymers or copolymers of olefin, such than ethylene or propylene, polyacrylates and polymethacrylates (PMA).
En particulier, une composition lubrifiante considérée selon l’invention peut comprendre de 1 à 15 % en poids, d’additif(s) améliorant l’indice de viscosité, par rapport au poids total de la composition lubrifiante.
Une composition lubrifiante considérée selon l’invention peut comprendre également au moins additif anti-mousse. Les additifs anti-mousse peuvent être choisis parmi les polymères polaires tels que les polyméthylsiloxanes ou les polyacrylates. In particular, a lubricating composition considered according to the invention may comprise from 1 to 15% by weight, of additive (s) improving the viscosity index, relative to the total weight of the lubricating composition. A lubricating composition considered according to the invention may also comprise at least anti-foam additive. The anti-foam additives can be chosen from polar polymers such as polymethylsiloxanes or polyacrylates.
En particulier, une composition lubrifiante considérée selon l’invention peut comprendre de 0,01 à 3% en poids d’additif(s) anti-mousse, par rapport au poids total de la composition lubrifiante. In particular, a lubricating composition considered according to the invention may comprise from 0.01 to 3% by weight of anti-foaming additive (s), relative to the total weight of the lubricating composition.
Comme évoqué précédemment, la mise en œuvre d’un ou plusieurs diesters de formule (I) requis selon l’invention à titre d’additif permet d’améliorer significativement les propriétés anti-usure de la composition lubrifiante comprenant un ou plusieurs additifs anti usure conventionnels. As mentioned above, the use of one or more diesters of formula (I) required according to the invention as an additive makes it possible to significantly improve the anti-wear properties of the lubricating composition comprising one or more anti-wear additives conventional.
Les propriétés anti-usure peuvent être évaluées selon une procédure basée sur la norme ASTM D2670, via l’utilisation d’un tribomètre, comme décrit dans les exemples qui suivent. The anti-wear properties can be evaluated according to a procedure based on standard ASTM D2670, via the use of a tribometer, as described in the examples which follow.
Une composition lubrifiante considérée selon l’invention peut être plus particulièrement une composition de grade selon la classification SAEJ300 défini par la formule (X)W(Y), dans laquelle X représente 0 ou 5 ; et Y représente un nombre entier allant de 4 à 30. Ce grade qualifie une sélection de compositions lubrifiantes spécialement destinées à une application moteur de véhicule automobile et qui satisfont notamment à des spécificités quantifiées vis-à-vis de différents paramètres tels que la viscosité à froid au démarrage, la pompabilité à froid, la viscosité cinématique à faible taux de cisaillement et la viscosité dynamique à fort taux de cisaillement. A lubricating composition considered according to the invention can more particularly be a grade composition according to the SAEJ300 classification defined by the formula (X) W (Y), in which X represents 0 or 5; and Y represents an integer ranging from 4 to 30. This grade qualifies a selection of lubricant compositions specially intended for an engine application of a motor vehicle and which in particular satisfy specific characteristics quantified with respect to various parameters such as the viscosity at cold at start-up, cold pumpability, kinematic viscosity at low shear rate and dynamic viscosity at high shear rate.
Le grade de viscosité d’une composition lubrifiante considérée selon l’invention peut être notamment choisi parmi : The viscosity grade of a lubricating composition considered according to the invention can in particular be chosen from:
- un grade selon la classification SAEJ300 défini par les formules (II) ou (III) - a grade according to the SAEJ300 classification defined by formulas (II) or (III)
0 W (Y) 5 W (Y) 0 W (Y) 5 W (Y)
(II) (III) (II) (III)
dans lesquelles Y représente un nombre entier allant de 4 à 20, en particulier allant de 4 à 16 ou de 4 à 12 ; ou in which Y represents an integer ranging from 4 to 20, in particular ranging from 4 to 16 or from 4 to 12; or
- un grade selon la classification SAEJ300 défini par les formules (IV) ou (V° - a grade according to the SAEJ300 classification defined by the formulas (IV) or (V °
(X) W 8 (X) W 12 (X) W 8 (X) W 12
(IV) (V)
dans lesquelles X représente 0 ou 5. (IV) (V) in which X represents 0 or 5.
Selon un mode de réalisation particulier, le grade selon la classification SAEJ300 d’une composition lubrifiante considérée selon l’invention est choisi parmi 0W4, 0W8, 0W12, 0W16, 0W20, 5W4, 5W8, 5W12, 5W16 et 5W20, de préférence choisi parmi 0W4, 0W8, 0W12, 0W16, 0W20 et 5W20. According to a particular embodiment, the grade according to the SAEJ300 classification of a lubricating composition considered according to the invention is chosen from 0W4, 0W8, 0W12, 0W16, 0W20, 5W4, 5W8, 5W12, 5W16 and 5W20, preferably chosen from 0W4, 0W8, 0W12, 0W16, 0W20 and 5W20.
En particulier, une composition lubrifiante considérée selon l’invention peut posséder un grade selon la classification SAEJ300 de 0W20 ou de 0W16. In particular, a lubricating composition considered according to the invention may have a grade according to the SAEJ300 classification of 0W20 or 0W16.
De manière avantageuse, la viscosité cinématique mesurée à 100 °C selon la norme ASTM D445 d’une composition lubrifiante considérée selon l’invention est comprise entre 3 et 15 mm2. s 1, en particulier entre 3 et 13 mm2. s 1. Advantageously, the kinematic viscosity measured at 100 ° C. according to standard ASTM D445 of a lubricating composition considered according to the invention is between 3 and 15 mm 2 . s 1 , in particular between 3 and 13 mm 2 . s 1 .
De manière avantageuse, la viscosité mesurée à haute température et haut cisaillement, HTHS (pour « high température high-shear viscosity measurement » en langue anglaise), mesurée à 150 °C, est égale ou supérieure à 1,7 mPa.s, de préférence comprise entre 1,7 et 3,7 mPa.s, avantageusement compris entre 2,3 et 3,7 mPa.s. Advantageously, the viscosity measured at high temperature and high shear, HTHS (for “high temperature high-shear viscosity measurement” in English), measured at 150 ° C, is equal to or greater than 1.7 mPa.s, preferably between 1.7 and 3.7 mPa.s, advantageously between 2.3 and 3.7 mPa.s.
La mesure HTHS est effectuée à haut cisaillement (106 s 1) et à 150 °C selon les méthodes normalisées CEC-L-36-A-90, ASTM D4683 et ASTMD4741. The HTHS measurement is carried out at high shear (10 6 s 1 ) and at 150 ° C. according to the standardized methods CEC-L-36-A-90, ASTM D4683 and ASTMD4741.
L’invention va maintenant être décrite au moyen des exemples suivants donnés bien entendu à titre illustratif et non limitatif de l’invention. The invention will now be described by means of the following examples, of course, given by way of illustration and without limitation of the invention.
EXEMPLESEXAMPLES
EXEMPLE 1 EXAMPLE 1
Préparation de compositions lubrifiantes comprenant un diester requis selon l’invention et de compositions comparatives Preparation of lubricating compositions comprising a diester required according to the invention and of comparative compositions
Des compositions lubrifiantes conformes à l’invention (Il et 12), mettant en œuvre un diester de formule (I), et des compositions comparatives (Cl et C2), exemptes de diester de formule (I), ont été formulées avec les composants et quantités (exprimées en pourcentage massique) indiqués dans le tableau 1 suivant. Lubricating compositions in accordance with the invention (II and 12), using a diester of formula (I), and comparative compositions (Cl and C2), free of diester of formula (I), were formulated with the components and quantities (expressed as percentage by mass) indicated in Table 1 below.
Les compositions lubrifiantes sont obtenues par simple mélange à température ambiante, des composants suivants :
Huile de base de groupe III (KV100 = 4,2 mm2/s, KV40 = 19,1 mm2/s, VI de 126) disponible commercialement par exemple auprès de la société SK Lubricantes sous le nom commercial « Yubase® 4 », The lubricating compositions are obtained by simple mixing at room temperature, of the following components: Group III base oil (KV100 = 4.2 mm 2 / s, KV40 = 19.1 mm 2 / s, VI of 126) commercially available, for example, from SK Lubricantes under the trade name "Yubase ® 4" ,
Paquet d’additifs 1 conventionnel comprenant un additif anti-usure (bis(dithiophosphate) de zinc et de bis[0,0-bis(2-éthylhexyle)], par exemple commercialisé sous le nom « OLOA® 269R »), des agents antioxydants, un agent modificateur de frottement, un dispersant et des détergents, One conventional additive package comprising an anti-wear additive (bis (dithiophosphate) and zinc bis [0,0-bis (2-ethylhexyl) phthalate], for example, sold under the name "OLOA 269R ®"), agents antioxidants, a friction modifying agent, a dispersant and detergents,
Paquet d’additifs 2 conventionnel comprenant un additif anti-usure (le zinc bis[0- (l,3-diméthylbutyl)] bis[0-(isopropyl)] bis(dithiophosphate)), des agents antioxydants, un agent modificateur de frottement, un dispersant et des détergents, Conventional additive package 2 including an anti-wear additive (zinc bis [0- (1,3-dimethylbutyl)] bis [0- (isopropyl)] bis (dithiophosphate)), antioxidants, a friction modifier , a dispersant and detergents,
Un polymère peigne polyméthacrylate disponible commercialement auprès de la société Evonik sous le nom commercial « Viscoplex® V3-200 », et éventuellement Un diester de formule (I) selon l’invention, obtenu par réaction d’estérification entre le dipropylène glycol et au moins deux acides gras nonanoïques. A comb polymer polymethylmethacrylate commercially available from Evonik under the trade name "Viscoplex ® V3-200", and optionally a diester of formula (I) according to the invention, obtained by esterification reaction of dipropylene glycol and at least two nonanoic fatty acids.
Tableau 1 Table 1
Les caractéristiques des compositions ainsi préparées sont présentées dans le tableau 2 suivant. The characteristics of the compositions thus prepared are presented in Table 2 below.
Tableau 2
( l 1 mesure de la viscosité à haute température et à haut cisaillement (HTHS pour l’acronyme anglais « high température high shear »), à un cisaillement de 106 s 1 et à 150 °C selon la méthode normalisée ASTM D4683 ; Table 2 (l 1 measurement of viscosity at high temperature and high shear (HTHS for the acronym “high temperature high shear”), at a shear of 10 6 s 1 and at 150 ° C according to the standardized method ASTM D4683;
(2) (3) viscosité cinématique à 40°C (KV40) et à l00°C (KV100) mesurées selon la norme ASTM D445-97 ; ( 2 ) (3) kinematic viscosity at 40 ° C (KV40) and at 100 ° C (KV100) measured according to standard ASTM D445-97;
(4) indice de viscosité (VI), mesuré selon la norme ASTM D2270-93 (4) viscosity index (VI), measured according to standard ASTM D2270-93
EXEMPLE 2 EXAMPLE 2
Evaluation des propriétés anti-usure Evaluation of anti-wear properties
Méthode d’évaluation Assessment method
Cette évaluation est basée sur une procédure selon la norme ASTM D2670, nécessitant Tutilisation d’un tribomètre FALEX et dont les conditions d’essai sont décrites ci-dessous. This evaluation is based on a procedure according to standard ASTM D2670, requiring the use of a FALEX tribometer and the test conditions of which are described below.
- éprouvettes : acier FALEX - test pieces: FALEX steel
- durée de rodage : 300 s ; - running-in time: 300 s;
- durée d’essai ; 180 min ; - test duration; 180 min;
- charge de rodage : 445 N ; - running-in load: 445 N;
- charge d’essai : 1335 N - test load: 1335 N
- vitesse : 290 tr/min ; - speed: 290 rpm;
- température ambiante. - ambient temperature.
Les résultats de l’essai sont présentés dans le tableau 3 suivant, et sont exprimés plus spécifiquement en pm ; plus la valeur obtenue est faible, meilleures sont les propriétés anti-usure de la composition évaluée. The results of the test are presented in Table 3 below, and are expressed more specifically in pm; the lower the value obtained, the better the antiwear properties of the composition evaluated.
Tableau 3
Les résultats montrent que l’ajout d’un diester de formule (I) selon l’invention aux compositions lubrifiantes permettent d’améliorer de manière significative leurs propriétés anti-usure.
Table 3 The results show that the addition of a diester of formula (I) according to the invention to the lubricating compositions makes it possible to significantly improve their anti-wear properties.
Claims
REVENDICATIONS
1. Utilisation d’un diester de formule (I) suivante : 1. Use of a diester of formula (I) below:
Ra-C(0)-0-([C(R)2]n-0)s-C(0)-Rb (I) R a -C (0) -0 - ([C (R) 2 ] n -0) s -C (0) -R b (I)
dans laquelle : in which :
- R représentent, indépendamment les uns des autres, un atome d’hydrogène ou un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, notamment méthyle ; - R represent, independently of each other, a hydrogen atom or a (Ci-Cs) alkyl group, linear or branched, in particular a methyl, ethyl or propyl group, in particular methyl;
- s vaut 1 ou 2 ; - s is 1 or 2;
- n vaut 1 , 2 ou 3 ; étant entendu que, lorsque s est différent de 1 , n peuvent être identiques ou différents ; et - n is 1, 2 or 3; it being understood that, when s is different from 1, n may be the same or different; and
- Ra et Rb, identiques ou différents, représentent indépendamment les uns des autres, des groupements hydrocarbonés, saturés ou insaturés, linéaires ou ramifiés, présentant un enchaînement linéaire de 2 à 11 atomes de carbone, de préférence de 3 à 8 atomes de carbone ; - R a and R b , identical or different, represent independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear chain of 2 to 11 carbon atoms, preferably 3 to 8 atoms carbon;
sous réserve que, lorsque s vaut 2 et n, identiques, valent 2, au moins l’un des groupe R représente un groupe (Ci-Cs)alkyle, linéaire ou ramifié ; et with the proviso that, when s is 2 and n, which are identical, are 2, at least one of the group R represents a (Ci-Cs) alkyl group, linear or branched; and
sous réserve que, lorsque s vaut 1 et n vaut 3, au moins l’un des groupes R lié au carbone en position bêta des atomes d’oxygène des fonctions esters représente un atome d’hydrogène, with the proviso that, when s is 1 and n is 3, at least one of the groups R bonded to the carbon in beta position of the oxygen atoms of the ester functions represents a hydrogen atom,
à titre d’additif pour améliorer les propriétés anti-usure d’une composition lubrifiante comprenant un ou plusieurs additif(s) anti-usure. as an additive for improving the anti-wear properties of a lubricating composition comprising one or more anti-wear additive (s).
2. Utilisation selon la revendication précédente, ledit diester de formule (I) étant de formule (F) : 2. Use according to the preceding claim, said diester of formula (I) being of formula (F):
Ra-C(0)-0-([C(R)2]n-0)-([C(R’)2]m-0)s-i-C(0)-Rb (r) dans laquelle : R a -C (0) -0 - ([C (R) 2 ] n -0) - ([C (R ') 2 ] m -0) if -C (0) -R b (r) in which :
- R et R’ représentent, indépendamment les uns des autres, un atome d’hydrogène ou un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, notamment un groupe méthyle ; - R and R ’represent, independently of each other, a hydrogen atom or a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, in particular a methyl group;
- s vaut 1 ou 2 ; - s is 1 or 2;
- n vaut 2 ; - n is 2;
- m vaut 2 ;
- Ra et Rb, identiques ou différents, représentent indépendamment les uns des autres, des groupements hydrocarbonés, saturés ou insaturés, linéaires ou ramifiés, présentant un enchaînement linéaire de 2 à 11 atomes de carbone, de préférence de 3 à 8 atomes de carbone ; - m is 2; - R a and R b , identical or different, represent independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear chain of 2 to 11 carbon atoms, preferably 3 to 8 atoms carbon;
sous réserve que, lorsque s vaut 2, au moins l’un des groupes R ou R’ représente un groupe (Ci-Cs)alkyle, linéaire ou ramifié. with the proviso that, when s is 2, at least one of the groups R or R ’represents a (Ci-Cs) alkyl group, linear or branched.
3. Utilisation selon la revendication précédente, ledit diester étant de formule (G), dans laquelle : 3. Use according to the preceding claim, said diester being of formula (G), in which:
- s vaut 2, - s is 2,
- l’un des groupes R représente un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, avantageusement méthyle, les autres représentant des atomes d’hydrogène ; et - one of the groups R represents a (Ci-Cs) alkyl group, linear or branched, in particular a methyl, ethyl or propyl group, advantageously methyl, the others representing hydrogen atoms; and
- l’un des groupes R’ représente un groupe (Ci-C5)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, avantageusement méthyle, les autres représentant des atomes d’hydrogène. - one of the groups R ’represents a linear or branched (Ci-C5) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl, the others representing hydrogen atoms.
4. Utilisation selon la revendication 2, le diester étant de formule (F) dans laquelle : 4. Use according to claim 2, the diester being of formula (F) in which:
- s vaut 1 , et - s is 1, and
- l’un des groupes R représente un groupe (Ci-Cs)alkyle, linéaire ou ramifié, en particulier un groupe méthyle, éthyle ou propyle, avantageusement méthyle, les autres représentant des atomes d’hydrogène. one of the groups R represents a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl, the others representing hydrogen atoms.
5. Utilisation selon l’une quelconque des revendications précédentes, dans laquelle le ou les diester(s) de formule (I) sont mis en œuvre à raison de 1 % à 30 % en poids, en particulier de 5 % à 30 % en poids, notamment de 5 % à 25 % en poids, de préférence de 5 % à 20 % en poids, par rapport au poids total de la composition lubrifiante. 5. Use according to any one of the preceding claims, in which the diester (s) of formula (I) are used in an amount of 1% to 30% by weight, in particular from 5% to 30% by weight. weight, in particular from 5% to 25% by weight, preferably from 5% to 20% by weight, relative to the total weight of the lubricating composition.
6. Utilisation selon l’une quelconque des revendications précédentes, ladite composition lubrifiante comprenant un ou plusieurs additif(s) anti-usure choisi(s) parmi les alkylthiophosphates métalliques, en particulier les alkylthiophosphates de zinc, et plus spécifiquement les dialkyldithiophosphates de zinc, de préférence choisi(s) parmi les composés de formule Zn((SP(S)(OR)(OR’))2, dans laquelle R et R’, identiques ou différents représentent, indépendamment les uns des autres, des groupements alkyles, linéaires ou ramifiés, comportant préférentiellement de 1 à 18 atomes de carbone.
6. Use according to any one of the preceding claims, said lubricant composition comprising one or more anti-wear additive (s) chosen from metal alkylthiophosphates, in particular zinc alkylthiophosphates, and more specifically zinc dialkyldithiophosphates, preferably chosen from the compounds of formula Zn ((SP (S) (OR) (OR ')) 2 , in which R and R', identical or different, represent, independently of one another, alkyl groups, linear or branched, preferably comprising from 1 to 18 carbon atoms.
7. Utilisation selon l’une quelconque des revendications précédentes, dans laquelle le ou lesdits additif(s) anti-usure sont présents en une teneur allant de 0,01 à 6 % en poids, en particulier de 0,05 à 4 % en poids, notamment de 0,1 à 2 % en poids, de préférence en une teneur inférieure ou égale à 1 % en poids, par rapport au poids total de ladite composition. 7. Use according to any one of the preceding claims, in which the said anti-wear additive (s) are present in a content ranging from 0.01 to 6% by weight, in particular from 0.05 to 4% by weight. weight, in particular from 0.1 to 2% by weight, preferably in a content less than or equal to 1% by weight, relative to the total weight of said composition.
8. Utilisation selon l’une quelconque des revendications précédentes, ladite composition lubrifiante étant une composition lubrifiante pour moteur, en particulier pour moteur de véhicule. 8. Use according to any one of the preceding claims, said lubricant composition being a lubricant composition for an engine, in particular for a vehicle engine.
9. Utilisation selon l’une quelconque des revendications précédentes, ladite composition lubrifiante comprenant au moins une huile de base choisie parmi les huiles de groupe II, III et IV de la classification API, en particulier au moins une huile de base de groupe III. 9. Use according to any one of the preceding claims, said lubricating composition comprising at least one base oil chosen from group II, III and IV oils of the API classification, in particular at least one group III base oil.
10. Utilisation selon l’une quelconque des revendications précédentes, ladite composition lubrifiante étant de grade selon la classification SAEJ300 défini par la formule (X)W(Y), dans laquelle X représente 0 ou 5 ; et Y représente un nombre entier allant de 4 à 10. Use according to any one of the preceding claims, said lubricant composition being of grade according to the classification SAEJ300 defined by the formula (X) W (Y), in which X represents 0 or 5; and Y represents an integer ranging from 4 to
30. 30.
11. Utilisation selon l’une quelconque des revendications précédentes, ladite composition lubrifiante comprenant en outre un ou plusieurs additifs choisis parmi les additifs modificateurs de frottement, les additifs extrême pression, les additifs détergents, les additifs antioxydants, les améliorants de l’indice de viscosité, les additifs abaisseurs du point d’écoulement, les agents dispersant, les agents anti-mousse, les épaississants, et leurs mélanges.
11. Use according to any one of the preceding claims, said lubricant composition further comprising one or more additives chosen from friction modifying additives, extreme pressure additives, detergent additives, antioxidant additives, index improving agents. viscosity, pour point lowering additives, dispersing agents, anti-foaming agents, thickeners, and mixtures thereof.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1860151A FR3088073B1 (en) | 2018-11-05 | 2018-11-05 | USE OF A DIESTER TO IMPROVE THE ANTI-WEAR PROPERTIES OF A LUBRICANT COMPOSITION |
| PCT/EP2019/080044 WO2020094546A1 (en) | 2018-11-05 | 2019-11-04 | Use of a diester to improve the anti-wear properties of a lubricant composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP3877488A1 true EP3877488A1 (en) | 2021-09-15 |
| EP3877488B1 EP3877488B1 (en) | 2023-06-07 |
Family
ID=65494388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19795025.6A Active EP3877488B1 (en) | 2018-11-05 | 2019-11-04 | Use of a diester to improve the anti-wear properties of a lubricant composition |
Country Status (8)
| Country | Link |
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| US (1) | US11820958B2 (en) |
| EP (1) | EP3877488B1 (en) |
| JP (1) | JP2022512880A (en) |
| KR (1) | KR20210110799A (en) |
| CN (1) | CN113166668B (en) |
| ES (1) | ES2953746T3 (en) |
| FR (1) | FR3088073B1 (en) |
| WO (1) | WO2020094546A1 (en) |
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| FR3083244B1 (en) | 2018-07-02 | 2020-07-17 | Total Marketing Services | COMPOSITION FOR COOLING AND LUBRICATING A PROPULSION SYSTEM OF AN ELECTRIC OR HYBRID VEHICLE |
| FR3105221B1 (en) * | 2019-12-20 | 2022-08-05 | Total Marketing Services | METHOD FOR PREPARING DIESTERS FROM UNSATURATED FATTY ALCOHOL AND DIESTERS THUS OBTAINED |
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| US3003968A (en) | 1958-03-03 | 1961-10-10 | Dow Chemical Co | Method of hydraulic transmission of power |
| US20050070450A1 (en) * | 2003-09-30 | 2005-03-31 | Roby Stephen H. | Engine oil compositions |
| JP4827381B2 (en) * | 2004-01-30 | 2011-11-30 | 出光興産株式会社 | Biodegradable lubricating oil composition |
| CN1786495B (en) * | 2004-12-07 | 2010-05-05 | 松下电器产业株式会社 | Hydrodynamic bearing device, and spindle motor and information device using the same |
| JP2006193723A (en) * | 2004-12-07 | 2006-07-27 | Matsushita Electric Ind Co Ltd | Liquid bearing device, spindle motor given by using the same, and information device |
| GB0703831D0 (en) * | 2007-02-28 | 2007-04-11 | Croda Int Plc | Engine lubricants |
| JP5288861B2 (en) | 2008-04-07 | 2013-09-11 | Ｊｘ日鉱日石エネルギー株式会社 | Lubricating oil composition |
| JP2010138316A (en) * | 2008-12-12 | 2010-06-24 | Alphana Technology Co Ltd | Bearing lubricant, bearing and disc driving unit |
| EP2440640A1 (en) * | 2009-06-12 | 2012-04-18 | Evonik RohMax Additives GmbH | A fluid having improved viscosity index |
| JP2011148970A (en) | 2009-12-24 | 2011-08-04 | Idemitsu Kosan Co Ltd | Base oil for cooling device, device-cooling oil obtained through blending of the base oil, device to be cooled by the cooling oil, and device cooling method using the cooling oil |
| US20120283162A1 (en) | 2009-12-28 | 2012-11-08 | Idemitsu Kosan Co., Ltd | Base oil for cooling of device, device-cooling oil containing the base oil, device to be cooled by the cooling oil, and device cooling method using the cooling oil |
| EP2547753A1 (en) | 2010-03-17 | 2013-01-23 | Shell Internationale Research Maatschappij B.V. | Lubricating composition |
| JP5647036B2 (en) | 2011-03-07 | 2014-12-24 | 出光興産株式会社 | Lubricating oil composition |
| US20130005622A1 (en) * | 2011-06-29 | 2013-01-03 | Exxonmobil Research And Engineering Company | Low viscosity engine oil with superior engine wear protection |
| JP2013032435A (en) * | 2011-08-01 | 2013-02-14 | Sanyo Chem Ind Ltd | Lubricant composition for bearing |
| CN102660362A (en) * | 2012-05-09 | 2012-09-12 | 上海金兆节能科技有限公司 | Trace lubricating oil for high-speed motor bearing and preparation method of trace lubricating oil |
| DE102013112454A1 (en) * | 2013-11-13 | 2015-05-28 | Pantere Gmbh & Co. Kg | lubricant composition |
| JP6218695B2 (en) * | 2013-12-16 | 2017-10-25 | 富士フイルム株式会社 | Lubricating oil composition for internal combustion engines of passenger and commercial four-wheeled vehicles |
| JP6300686B2 (en) * | 2014-01-31 | 2018-03-28 | Ｅｍｇルブリカンツ合同会社 | Lubricating oil composition |
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| CN104498136A (en) * | 2014-11-28 | 2015-04-08 | 苏州阿莫夫工贸有限公司 | Total-efficiency anti-wear additive for engine lubricating oil |
| KR102595396B1 (en) * | 2015-03-20 | 2023-10-27 | 산요가세이고교 가부시키가이샤 | Viscosity index improver, lubricant composition, and method for manufacturing lubricant composition |
| JP6789615B2 (en) | 2015-03-31 | 2020-11-25 | 出光興産株式会社 | Lubricating oil composition for transmission |
| JP6155414B1 (en) * | 2015-12-04 | 2017-06-28 | Ｎｏｋクリューバー株式会社 | Lubricant composition |
| FR3048976B1 (en) | 2016-03-15 | 2020-02-07 | Total Marketing Services | LUBRICATING COMPOSITION BASED ON POLYALKYLENE GLYCOLS |
| FR3048977B1 (en) | 2016-03-15 | 2020-02-07 | Total Marketing Services | LUBRICATING COMPOSITION BASED ON POLYALKYLENE GLYCOLS |
| US20180100117A1 (en) | 2016-10-07 | 2018-04-12 | Exxonmobil Research And Engineering Company | Lubricating oil compositions for electric vehicle powertrains |
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| US20180258365A1 (en) * | 2017-03-08 | 2018-09-13 | Chevron Japan Ltd. | Low viscosity lubricating oil composition |
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| FR3083244B1 (en) | 2018-07-02 | 2020-07-17 | Total Marketing Services | COMPOSITION FOR COOLING AND LUBRICATING A PROPULSION SYSTEM OF AN ELECTRIC OR HYBRID VEHICLE |
-
2018
- 2018-11-05 FR FR1860151A patent/FR3088073B1/en active Active
-
2019
- 2019-11-04 CN CN201980080816.0A patent/CN113166668B/en active Active
- 2019-11-04 WO PCT/EP2019/080044 patent/WO2020094546A1/en unknown
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- 2019-11-04 US US17/291,118 patent/US11820958B2/en active Active
- 2019-11-04 EP EP19795025.6A patent/EP3877488B1/en active Active
- 2019-11-04 KR KR1020217017243A patent/KR20210110799A/en unknown
- 2019-11-04 JP JP2021523694A patent/JP2022512880A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP3877488B1 (en) | 2023-06-07 |
| ES2953746T3 (en) | 2023-11-15 |
| CN113166668A (en) | 2021-07-23 |
| KR20210110799A (en) | 2021-09-09 |
| JP2022512880A (en) | 2022-02-07 |
| CN113166668B (en) | 2022-09-27 |
| FR3088073B1 (en) | 2021-07-23 |
| US11820958B2 (en) | 2023-11-21 |
| US20210380898A1 (en) | 2021-12-09 |
| WO2020094546A1 (en) | 2020-05-14 |
| FR3088073A1 (en) | 2020-05-08 |
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