EP0390664B1 - Nouveaux composés thiophosphores leur préparation et leur utilisation comme additifs pour lubrifiants - Google Patents
Nouveaux composés thiophosphores leur préparation et leur utilisation comme additifs pour lubrifiants Download PDFInfo
- Publication number
- EP0390664B1 EP0390664B1 EP90400818A EP90400818A EP0390664B1 EP 0390664 B1 EP0390664 B1 EP 0390664B1 EP 90400818 A EP90400818 A EP 90400818A EP 90400818 A EP90400818 A EP 90400818A EP 0390664 B1 EP0390664 B1 EP 0390664B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition according
- phosphorus
- mass
- masse
- additive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title description 17
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000003879 lubricant additive Substances 0.000 title 1
- 239000000654 additive Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 21
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 claims description 18
- 239000011575 calcium Substances 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 230000000996 additive effect Effects 0.000 claims description 17
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- -1 hydrogen compound Chemical class 0.000 claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 10
- 239000011707 mineral Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004327 boric acid Substances 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 230000001050 lubricating effect Effects 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 239000004519 grease Substances 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 238000001914 filtration Methods 0.000 description 9
- 239000012429 reaction media Substances 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000005069 Extreme pressure additive Substances 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 239000007866 anti-wear additive Substances 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 230000008030 elimination Effects 0.000 description 5
- 238000003379 elimination reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000010705 motor oil Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000003871 sulfonates Chemical class 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- BTHAQRDGBHUQMR-UHFFFAOYSA-N [S]P(=O)=O Chemical compound [S]P(=O)=O BTHAQRDGBHUQMR-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000001246 colloidal dispersion Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 2
- PQMFVUNERGGBPG-UHFFFAOYSA-N (6-bromopyridin-2-yl)hydrazine Chemical compound NNC1=CC=CC(Br)=N1 PQMFVUNERGGBPG-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229910001018 Cast iron Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- QBCOASQOMILNBN-UHFFFAOYSA-N didodecoxy(oxo)phosphanium Chemical compound CCCCCCCCCCCCO[P+](=O)OCCCCCCCCCCCC QBCOASQOMILNBN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- OTYNBGDFCPCPOU-UHFFFAOYSA-N phosphane sulfane Chemical compound S.P[H] OTYNBGDFCPCPOU-UHFFFAOYSA-N 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- JJJPTTANZGDADF-UHFFFAOYSA-N thiadiazole-4-thiol Chemical class SC1=CSN=N1 JJJPTTANZGDADF-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
- C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
-
- 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
- C10M125/00—Lubricating compositions characterised by the additive being an inorganic material
- C10M125/14—Water
-
- 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
- C10M125/00—Lubricating compositions characterised by the additive being an inorganic material
- C10M125/24—Compounds containing phosphorus, arsenic or antimony
-
- 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
- C10M125/00—Lubricating compositions characterised by the additive being an inorganic material
- C10M125/26—Compounds containing silicon or boron, e.g. silica, sand
-
- 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
- C10M129/04—Hydroxy compounds
- C10M129/06—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
-
- 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
- C10M129/04—Hydroxy compounds
- C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
-
- 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
- C10M129/26—Carboxylic acids; Salts thereof
- C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M129/30—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/16—Amides; Imides
-
- 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/123—Reaction products obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic compounds
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Definitions
- the present invention relates to new thiophosphorus compounds soluble in mineral oils obtained by reaction of at least one phosphorus sulfide with at least one so-called "overbased" detergent sulfonate.
- an overbased detergent sulfonate can be defined as consisting of a surfactant consisting essentially of an alkaline or alkaline earth salt of a sulfonic acid containing oleophilic groups and which keeps acid salts in colloidal dispersion.
- weak minerals such as CO2, H2S and alkaline or alkaline earth bases.
- the reaction product between the phosphorus sulfide and the overbased detergent sulfonate can optionally be treated with at least one active hydrogen compound which can be water, an alcohol, a phenol, a carboxylic acid, a ester-acid, a mineral acid, a mineral base, an amine, an amide or a mercaptan.
- active hydrogen compound can be water, an alcohol, a phenol, a carboxylic acid, a ester-acid, a mineral acid, a mineral base, an amine, an amide or a mercaptan.
- the present invention also relates to the preparation of these new thiophosphorus compounds and their use as additives in mineral and synthetic lubricants.
- these new additives have anti-wear and extreme-pressure properties which are particularly advantageous for application to engine oils, gear oils, hydraulic fluids, lubricating greases or oils for working with metals. .
- Antiwear and extreme pressure additives are incorporated into lubricants when they are intended to lubricate organs subjected to significant mechanical stresses, such as distribution in heat engines, gears, bearings or stops. Significant mechanical stresses also appear during the machining of metals, whether cutting or forming.
- transmission oils two types of additive are widely used: phospho-sulfur additives and additives based on potassium borate dispersion.
- the main drawback of mineral oils containing phospho-sulfur additives is their thermal instability, which begins to manifest from 120-130 ° C. However, it is not uncommon for temperatures of 150 ° C to be reached in the transmissions of heavy goods vehicles or passenger cars used under severe conditions. Transmission oils based on potassium borate are significantly more thermally stable, but are sensitive to water, which is unacceptable for certain uses. More effective antiwear and extreme pressure additives, more thermally stable and having less interactions with other additives in the formulations are actively sought.
- micellar thiophosphorus compounds of the present invention may be generally defined as being obtained by reaction of at least one overbased sulfonate (A) with a phosphorus sulfide (B), the reaction product possibly being brought into contact with at least one hydrogen compound active (C).
- a and B, and optionally the subsequent treatment with C can advantageously be carried out in a solvent (D).
- Compound A is an overbased sulfonate obtained from at least one alkali or alkaline earth metal salt of at least one acid compound chosen from sulfonic acids, natural or synthetic.
- the overbasification of the alkali or alkaline earth metal salts of these acids is generally carried out in the presence of a promoter, by treating an excess of oxide or hydroxide of alkali or alkaline earth metal suspended in the reaction medium. , by a weak acid such as CO2, SO2, H2S, or H3BO3.
- the most used cations for overbasification are sodium, magnesium, calcium and barium used in the form of their oxide or hydroxide.
- the promoter is an alcohol, particularly methanol, an alkylphenol or an amino compound such as ammonia, an amine or an amino alcohol.
- the most commonly used weak acid is CO2.
- overbased additives The preparation of overbased additives is well known and is described for example in the patents: US 2,865,956, 3,150,088, 3,537,996, 3,830,739, 3,865,737, 4,148,740 and 4,505,830 and the French patent 2 101 813.
- overbasing reaction which use in particular preformed carbonates from alkoxides and CO2 before being brought into contact with the alkaline or alkaline earth salt of the acid compound; they are described in particular in US patents 2,956,018, 3,932,289 and 4,104,180.
- the sulfonic acids for the manufacture of overbased sulfonates which can be used according to the invention are known and described in numerous patents, for example in French patent 2 101 813, pages 5 and 6.
- the hydrocarbon portion of the molecule advantageously has a molecular weight at less than 370 to ensure the miscibility of the corresponding sulfonates in mineral oils.
- alkenyl hydrocarbons such as polyisobutenes (US patent 4,159,956)
- alkylaryl hydrocarbons such as for example post-dodecylbenzenes obtained as tail product of the manufacture of dodecylbenzene.
- overbased compounds A preferred according to the invention are the sodium or calcium sulfonates overbased with sodium carbonate or calcium carbonate.
- the overbased sulfonates A that can be used according to the invention have an alkalinity expressed in terms of TBN (equivalent alkalinity expressed in milligrams of KOH per g of product) between 50 and 550 (or from 0.9 to 10 basic equivalents per kg) and preferably between 150 and 450 (i.e. 2.7 to 8 basic equivalents per kg).
- TBN equivalent alkalinity expressed in milligrams of KOH per g of product
- 150 and 450 i.e. 2.7 to 8 basic equivalents per kg.
- Compound B is a phosphorus sulfide such as P4S7, P4S9, P4S10.
- P4S10 is the preferred phosphorus sulfide according to the invention.
- the molar quantity of compound C introduced relative to the molar quantity of phosphorus provided by the phosphorus sulphide can vary in a ratio of between 0.1 and 5, and preferably between 0.3 and 3.
- the preferred compounds C according to the invention are ammonia, isopropanol, dialkylphosphites, boric acid, mercaptans, in particular derivatives of dimercaptothiadiazole.
- the solvent D possibly used makes it possible to reduce the viscosity of the reaction medium and thus to improve the contact of the reactants.
- solvents which can be used according to the invention, mention may be made of cyclohexane, toluene, xylenes and generally hydrocarbon fractions having a boiling range of between 60 and 150 ° C and preferably between 90 and 120 ° C.
- the additives obtained according to the invention may have a certain reactivity with respect to copper alloys.
- the use of sequestering additives of the dimercaptothiadiazole type at doses of between 0.25 and 0.75% by mass in the final formulations leads to entirely satisfactory behavior with respect to copper.
- the required dose is lower when compound C is itself a mercaptothiadiazole derivative. It can range, for example, up to 0.5% by mass.
- Another characteristic of the present invention is that, within the defined limits, the products obtained retain the colloidal state by giving solutions in the hydrocarbons perfectly clear and stable over time.
- the process for manufacturing the compounds according to the invention comprises the following stages:
- Step 1
- the reaction of phosphorus sulfide on overbased sulfonate can be carried out at a pressure between atmospheric pressure and about 5 bar absolute (0.5 MPa), at a temperature between 60 and 130 ° C and preferably between 85 and 120 ° C.
- the reaction between the phosphorus sulfide, solid reagent and the overbased additive is facilitated by good stirring of the reaction medium and by the possible use of a hydrocarbon solvent D.
- the phosphorus sulfide can be gradually introduced into the reaction medium, but it can also be introduced entirely at the start of handling into the overbased compound optionally dissolved in a hydrocarbon solvent, provided that the temperature of the reaction medium is less than about 60 ° C.
- the reaction is then started by gradually raising the temperature in the ranges indicated above.
- Compound C with active hydrogen can be in gaseous, liquid or solid form and the means of introduction into the reaction medium will be appropriate to its physical state.
- the reaction can be carried out at a pressure between atmospheric pressure and about 5 bar absolute (0.5 MPa), at a temperature between 60 and 130 ° C and preferably between 85 and 120 ° C.
- filtration and elimination of solvents and any excess of reagent.
- the filtration step is not always necessary, steps 1 and 2 leading in most cases to homogeneous liquid mixtures.
- filtration can be carried out before the elimination of solvent D, for example on simple cellulose disks, or on layers of filtering agents of the diatomite type or of natural silica of volcanic origin. Filtration can also be carried out after removal of the solvents. In this case, it is advantageous to perform the filtration hot, for example from 90 to 120 ° C and under a pressure of 2 to 5 bars.
- the distillation of the solvent can be carried out in the reactor itself.
- the elimination of the last traces is facilitated by a nitrogen stripping. It can also be carried out in a thin film evaporator.
- Example 6 The procedure is as in Example 6 until complete reaction of the P4S10. The temperature being maintained at 90 ° C., 49.5 g of didodecylphosphite dissolved in 50 ml of toluene are introduced over 1 hour. Then the temperature is brought to 115 ° C. and is maintained for 3 hours.
- the anti-wear efficiency is evaluated on a 4-ball machine operating for 1 hour under loads of 40 and 60 daN at a speed of 1500 rpm, according to the NF E48-617 method.
- the average footprint diameter observed on the 3 lower balls are as follows:
- the extreme pressure properties in the lubricating oils of the products according to the invention were measured on an FZG gear machine according to the CEC method L-07-A-71 with the procedure A / 16.6 / 90, that is to say that is, using the type A gear, with a circumferential speed at the pitch diameter of 16.6 m / s and at a temperature of 90 ° C at the start of each load bearing.
- the mineral oil used is the base 130 N described above. Method B of visual rating was used.
- the extreme pressure efficiency is all the more pronounced the higher the load level reached.
- the temperature of the oil was also recorded at the end of the bearing 12 which is in relation to the forces dissipated in the friction. A lower temperature translates to a lower coefficient of friction under the conditions of the test.
- the results obtained are shown in the following table:
- the objective of this test was to replace the antiwear additive and the detergent additive with an additive according to the invention.
- a conventional dispersant additive of the succinimide type usually used to meet the requirements of cold dispersivity was used.
- test bench is driven by an electric motor and operates according to the following cycle: 1 minute at 750 rpm 2 minutes at 1500 rpm
- the springs, under maximum lift, are rated at 1200 N.
- the duration of the test is 50 hours and the oil temperature is regulated at 50 ° C.
- the rockers are weighed and rated according to a scale which defines four standard aspects.
- This test uses a PEUGEOT PC7 bridge to which torque peaks of the order of 340 Nm are applied.
- the crown is examined without dismantling all the series of 20 torque peaks.
- the test is continued up to 80 peaks of torque, after which the bridge is dismantled and the surfaces of the pinion and the crown are examined.
- the result is given as a percentage of the bearing surface deteriorated by seizing (scoring).
- the additives are compared in an identical base oil (100 neutral solvent).
- a comparative test was carried out with an extreme pressure additive marketed under the name of ANGLAMOL 99 (registered trademark), extreme pressure additive widely used in hypoid bridges.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8904345A FR2645168B1 (fr) | 1989-03-30 | 1989-03-30 | Nouveaux composes thiophosphores, leur preparation et leur utilisation comme additifs pour lubrifiants |
| FR8904345 | 1989-03-30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0390664A2 EP0390664A2 (fr) | 1990-10-03 |
| EP0390664A3 EP0390664A3 (en) | 1990-12-12 |
| EP0390664B1 true EP0390664B1 (fr) | 1993-08-04 |
Family
ID=9380324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90400818A Expired - Lifetime EP0390664B1 (fr) | 1989-03-30 | 1990-03-23 | Nouveaux composés thiophosphores leur préparation et leur utilisation comme additifs pour lubrifiants |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5080812A (ja) |
| EP (1) | EP0390664B1 (ja) |
| JP (1) | JP2916644B2 (ja) |
| CA (1) | CA2013458C (ja) |
| DE (1) | DE69002511T2 (ja) |
| DK (1) | DK0390664T3 (ja) |
| ES (1) | ES2060085T3 (ja) |
| FR (1) | FR2645168B1 (ja) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5256319A (en) * | 1989-03-30 | 1993-10-26 | Institut Francais Du Petrole | New thiophosphoretted compounds, their preparation and their use as additives for lubricants |
| FR2681872B1 (fr) * | 1991-09-30 | 1993-12-24 | Inst Francais Du Petrole | Produits collouidaux renfermant du bore et du phosphore, leur preparation et leur utilisation comme additifs pour lubrifiants. |
| MX9305120A (es) * | 1992-09-04 | 1994-03-31 | Lubrizol Corp | Composiciones sobrebasificadas sulfuradas. |
| FR2698018B1 (fr) * | 1992-11-18 | 1995-01-20 | Inst Francais Du Petrole | Produits colloïdaux renfermant du bore, et/ou du soufre, et/ou du phosphore, leur préparation et leur utilisation comme additifs pour lubrifiants. |
| FR2698019B1 (fr) * | 1992-11-18 | 1995-02-24 | Inst Francais Du Petrole | Produits colloïdaux contenant du calcium et/ou du magnésium, ainsi que du bore et/ou du phosphore et/ou du soufre, leur préparation et leur utilisation comme additifs pour lubrifiants. |
| FR2709076B1 (fr) * | 1993-08-18 | 1995-10-06 | Inst Francais Du Petrole | Produits colloïdaux renfermant du calcium, et/ou du magnésium, ainsi que du souffre et de l'azote, leur préparation et leur utilisation notamment comme additifs dans les huiles lubrifiantes. |
| FR2716891B1 (fr) * | 1994-03-03 | 1996-06-14 | Inst Francais Du Petrole | Produits colloïdaux contenant du calcium, du baryum et/ou du magnésium ainsi que du bismuth, modifiés par action d'acides carboxyliques contenant du soufre et éventuellement de l'azote. |
| FR2755377B1 (fr) * | 1996-11-06 | 1999-01-08 | Inst Francais Du Petrole | Produits thio-phosphores colloidaux derives de chaux colloidale, preparation et utilisations |
| US5985805A (en) * | 1994-07-06 | 1999-11-16 | Institut Francais Du Petrole | Colloidal thio-phosphorous products derived from colloidal lime, their preparation and uses |
| FR2733165B1 (fr) * | 1995-04-20 | 1997-06-13 | Inst Francais Du Petrole | Carbonates alcalins ou alcalino-terreux colloidaux contenant un compose de calcium,de phospore et de soufre sous forme miscellisee |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB590885A (en) * | 1944-01-17 | 1947-07-31 | Standard Oil Dev Co | Improvements relating to petroleum hydrocarbon products and the manufacture of addition agents therefor |
| US2451345A (en) * | 1944-10-24 | 1948-10-12 | Standard Oil Dev Co | Compounded lubricating oil |
| US2698296A (en) * | 1952-07-28 | 1954-12-28 | Standard Oil Co | Process for preparing lubricating oil additive and products |
| US2956018A (en) * | 1955-07-01 | 1960-10-11 | Continental Oil Co | Metal containing organic compositions and method of preparing the same |
| US3132101A (en) * | 1956-05-21 | 1964-05-05 | Sinclair Research Inc | Detergent and anti-oxidant lubricant |
| BE668916A (ja) * | 1957-12-06 | |||
| US3492231A (en) * | 1966-03-17 | 1970-01-27 | Lubrizol Corp | Non-newtonian colloidal disperse system |
| US3474035A (en) * | 1967-03-20 | 1969-10-21 | Texaco Inc | Lubricating oil containing overbased sulfurized calcium alkylphenolate |
| US3489682A (en) * | 1968-03-01 | 1970-01-13 | Lubrizol Corp | Metal salt compositions |
| GB1235896A (en) * | 1968-05-24 | 1971-06-16 | Mobil Oil Corp | Multifunctional fluid |
| US4328111A (en) * | 1978-11-20 | 1982-05-04 | Standard Oil Company (Indiana) | Modified overbased sulfonates and phenates |
| US4804489A (en) * | 1987-10-29 | 1989-02-14 | The Lubrizol Corporation | Low molecular weight viscosity modifying compositions |
-
1989
- 1989-03-30 FR FR8904345A patent/FR2645168B1/fr not_active Expired - Fee Related
-
1990
- 1990-03-23 DK DK90400818.2T patent/DK0390664T3/da active
- 1990-03-23 EP EP90400818A patent/EP0390664B1/fr not_active Expired - Lifetime
- 1990-03-23 DE DE90400818T patent/DE69002511T2/de not_active Expired - Fee Related
- 1990-03-23 ES ES90400818T patent/ES2060085T3/es not_active Expired - Lifetime
- 1990-03-29 US US07/500,827 patent/US5080812A/en not_active Expired - Fee Related
- 1990-03-30 JP JP2087308A patent/JP2916644B2/ja not_active Expired - Lifetime
- 1990-03-30 CA CA002013458A patent/CA2013458C/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02286791A (ja) | 1990-11-26 |
| FR2645168B1 (fr) | 1993-02-05 |
| DE69002511T2 (de) | 1993-11-18 |
| EP0390664A3 (en) | 1990-12-12 |
| JP2916644B2 (ja) | 1999-07-05 |
| FR2645168A1 (fr) | 1990-10-05 |
| EP0390664A2 (fr) | 1990-10-03 |
| CA2013458C (fr) | 2002-04-23 |
| ES2060085T3 (es) | 1994-11-16 |
| CA2013458A1 (fr) | 1990-09-30 |
| US5080812A (en) | 1992-01-14 |
| DE69002511D1 (de) | 1993-09-09 |
| DK0390664T3 (da) | 1993-12-06 |
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