EP0271368B1 - Compositions d'oléfines polysulfurées, leur préparation et leur utilisation comme additifs pour lubrifiants - Google Patents
Compositions d'oléfines polysulfurées, leur préparation et leur utilisation comme additifs pour lubrifiants Download PDFInfo
- Publication number
- EP0271368B1 EP0271368B1 EP87402252A EP87402252A EP0271368B1 EP 0271368 B1 EP0271368 B1 EP 0271368B1 EP 87402252 A EP87402252 A EP 87402252A EP 87402252 A EP87402252 A EP 87402252A EP 0271368 B1 EP0271368 B1 EP 0271368B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition according
- polysulfide
- aliphatic
- proportion
- radical
- 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
- 239000000203 mixture Substances 0.000 title claims description 45
- 150000001336 alkenes Chemical class 0.000 title claims description 26
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title description 6
- 239000003879 lubricant additive Substances 0.000 title 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 45
- -1 aliphatic monoolefin Chemical class 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 239000011593 sulfur Substances 0.000 claims description 25
- 239000003921 oil Substances 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 125000004429 atom Chemical group 0.000 claims description 20
- 229920001021 polysulfide Polymers 0.000 claims description 20
- 239000000654 additive Substances 0.000 claims description 19
- 239000005077 polysulfide Substances 0.000 claims description 18
- 150000008117 polysulfides Polymers 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 238000010992 reflux Methods 0.000 claims description 14
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 230000000996 additive effect Effects 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 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 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 239000012208 gear oil Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 239000010688 mineral lubricating oil Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Chemical group 0.000 claims description 2
- 239000001301 oxygen Chemical group 0.000 claims description 2
- 239000010689 synthetic lubricating oil Substances 0.000 claims description 2
- 238000005555 metalworking Methods 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 235000001508 sulfur Nutrition 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 229920013639 polyalphaolefin Polymers 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 230000001476 alcoholic effect Effects 0.000 description 8
- 239000000314 lubricant Substances 0.000 description 8
- 239000005069 Extreme pressure additive Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000010687 lubricating oil Substances 0.000 description 7
- 239000011707 mineral Substances 0.000 description 7
- 235000010755 mineral Nutrition 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 229910052979 sodium sulfide Inorganic materials 0.000 description 5
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- UCYWDWSKWUEDSC-UHFFFAOYSA-M disodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[Na+].[SH-] UCYWDWSKWUEDSC-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000005673 monoalkenes Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- BDFAOUQQXJIZDG-UHFFFAOYSA-N 2-methylpropane-1-thiol Chemical compound CC(C)CS BDFAOUQQXJIZDG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- WGJCBBASTRWVJL-UHFFFAOYSA-N 1,3-thiazolidine-2-thione Chemical compound SC1=NCCS1 WGJCBBASTRWVJL-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 1
- 229940054266 2-mercaptobenzothiazole Drugs 0.000 description 1
- MPBLPZLNKKGCGP-UHFFFAOYSA-N 2-methyloctane-2-thiol Chemical compound CCCCCCC(C)(C)S MPBLPZLNKKGCGP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000013556 antirust agent Substances 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 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
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
- 229940113165 trimethylolpropane Drugs 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/02—Sulfurised compounds
- C10M135/04—Hydrocarbons
-
- 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
- C10M2203/06—Well-defined aromatic 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
- 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
-
- 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
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
-
- 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
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- 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
- C10M2207/286—Esters of polymerised unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
-
- 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
-
- 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
- C10M2223/042—Metal salts thereof
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/02—Bearings
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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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
-
- 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
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- 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
- C10N2040/20—Metal working
-
- 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
- C10N2040/20—Metal working
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
-
- 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
- C10N2040/20—Metal working
- C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
-
- 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
- C10N2040/20—Metal working
- C10N2040/241—Manufacturing joint-less pipes
-
- 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
- C10N2040/20—Metal working
- C10N2040/242—Hot working
-
- 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
- C10N2040/20—Metal working
- C10N2040/243—Cold working
-
- 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
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
-
- 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
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/245—Soft metals, e.g. aluminum
-
- 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
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/246—Iron or steel
-
- 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
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/247—Stainless steel
Definitions
- the invention relates to the field of organic sulfur additives used in particular to improve the extreme pressure properties of lubricants; it relates more particularly to new products of the polysulphurized olefin type, their preparation and their use as additives for mineral or synthetic lubricants.
- JI is indicated in the single example that the product has a sulfur content of 49% by mass and a viscosity at 37.8 ° C (100 ° F) of 8.6 mm 2 / s (cSt).
- the products thus prepared are polysulphurized olefins, which can have a sulfur content generally ranging up to approximately 45-65% by mass. Their kinematic viscosity at 100 ° C varies according to their sulfur content. It can be around 4 to 20 mm 2 / s. Their halogen content (mainly chlorine) is generally less than about 1% by mass and more often than about 0.6% by mass.
- PAO hydrogenated polyalphaolefins
- United States patent US-A-3 873 454 describes an extreme pressure additive for lubricants obtained by reaction of isobutylene and a sulfur halide to form an "adduct", followed by the reaction of said "adduct" with an alkaline mercaptate, in an inert medium to form the compound of formula:
- the alkaline mercaptate used can be sodium, potassium, lithium or calcium mercaptate.
- the reaction medium is generally a lower alcohol (C 1 to C 4 ).
- the desired compound (which has a sulfur content of about 53%) is obtained with a yield of about 45% by weight, the remaining 55% consisting of a mixture of sulfides and unsaturated polysulfides.
- the desired compound is finally obtained in the form of a solid, which is separated and purified.
- the monoolefin is used more particularly in an amount of 1.5 to 2.5 moles per mole of mono- and / or sulfur dichloride. It is generally introduced into the liquid mono- and / or dichloride at 20-80 ° C, more specifically at 30-50 ° C.
- the adduct, or "adduct”, obtained at the end of step (1) consists of a mixture of sulfur compounds in which the average proportion of sulfur can be approximately 1 to 2 gram atoms per mole , depending on whether sulfur dichloride, sulfur monochloride or a mixture of the two is used at the start.
- the proportion of chlorine is approximately 2 gram atoms per mole of product.
- the mercaptate polysulphides of general formula R 3- S x M used in step (2) can be more particularly prepared by reaction, preferably in alcoholic medium, of at least one mercaptan of general formula R 3 SH with a mineral base MOH, R 3 and M being defined as above, then with elemental sulfur in a suitable proportion so that the average value of x in the formula of the product obtained is approximately 1.2 to 7.
- mercaptans of formula R 3 SH which can advantageously be used to prepare mercaptate-polysulphides
- the reaction between the mercaptan and the mineral base is generally carried out at a temperature of 20 to 100 ° C.
- the alcoholic medium can comprise at least one aliphatic monoalcohol containing, for example, from 1 to 5 carbon atoms. Most often methanol is used. In general, 200 to 400 ml of aliphatic monoalcohol are used per mole of mercaptan involved.
- the product obtained is a sodium mercaptate, potassium or ammonium of formula R 3- SM (M representing Na, K or NH 4 ).
- the mercaptate thus formed is reacted with elemental sulfur, brought into play in a proportion ranging for example from about 0.2 to 10 gram atoms per mole of mercaptate. This reaction can be carried out at a temperature of 20-100 ° C.
- step (2) where the mercaptate-polysulfide of formula R 3 S X M is reacted, preferably in an alcoholic medium, with "adduct" obtained at the end of step (1 ), said "adduct” is generally added to the alcoholic solution of said mercaptate-polysulfide in a proportion such that said mercaptate-polysulfide represents a molar excess of about 0.1 to 70% relative to the stoichiometry of 2 moles per mole of said "adduct", the reaction medium being maintained for example at a temperature ranging from -10 ° C. to the reflux temperature of the alcoholic solvent involved.
- a polysulphurized olefin composition is obtained which can then be treated, in a step (3), with an alkaline aqueous solution, more particularly an aqueous solution of soda or potassium hydroxide having example a concentration of about 1 to 50% by mass.
- an alkaline aqueous solution more particularly an aqueous solution of soda or potassium hydroxide having example a concentration of about 1 to 50% by mass.
- the amount of alkaline solution used can for example be from 0.1 to 5 times the mass amount of crude polysulphurized olefin to be treated.
- the polysulfurized olefin compositions of the invention may have a sulfur content of about 25 to 60% by mass; their chlorine content is generally less than 0.1% by mass, most often less than 0.05% by mass. They can advantageously be used as extreme pressure additives for lubricating oils.
- a first application of the polysulfurized olefin compositions of the invention relates more particularly to the formulation of oils intended for the lubrication of gears.
- the base oils can be of mineral or synthetic origin.
- Synthetic oils include in particular oligomers of olefins such as triene, tetra- and pentamer of decene-1 obtained by oligomerization in the presence of LEWIS acids.
- Other ⁇ -olefins can of course be used, for example Ce to C 14 ⁇ -olefins.
- alkylbenzenes such as mono and dialkylbenzenes, or alternatively synthetic esters originating from mono- or polycarboxylic acids (such as sebacic acid, fatty acids, etc.) and monoalcohols or polyols, (such as 2-ethyl hexanol, trimethylol-propane, etc.).
- mono- or polycarboxylic acids such as sebacic acid, fatty acids, etc.
- monoalcohols or polyols such as 2-ethyl hexanol, trimethylol-propane, etc.
- the polysulphurized olefins considered can then be added to the lubricating oils at concentrations ranging for example from 0.5 to 10% by mass.
- additives can be used in combination with phosphorus additives, such as metallic dialkyl- or diaryldithiophosphates, phosphites and organic phosphates.
- antioxidants such as antioxidants, anti-rust agents, copper passivators, anti-foam agents, friction reducers, in the usual proportions.
- a second application of the polysulphurized olefin compositions of the invention as extreme pressure additives for lubricants relates more particularly to the formulation of oils intended for working with metals (cutting, forming, etc.).
- the concentration of additive used is generally from 0.1 to 20% and preferably from 0.5 to 5% by mass relative to the lubricating oil.
- other conventional additives can be added, such as chlorinated paraffins in a proportion corresponding for example to 2-10% by mass of chlorine relative to the lubricating oil.
- Example 4 is given for comparison.
- Example 1 The experiment of Example 1 is repeated under the same operating conditions, but this time 76.8 g of sulfur in flower (2.4 gram atoms) is used; the S / mercaptan molar ratio used is then 1/1.
- Example 1 The experiment of Example 1 was repeated once again, but this time no elemental sulfur was used.
- Tests have been carried out demonstrating the extreme pressure properties of additives prepared according to some of the preceding examples on the one hand in formulations of the gear oil type and, on the other hand, in formulations of the working oil type metals.
- Example 3 The extreme pressure properties of the additive obtained in Example 3 are evaluated from a formulation of the metal cutting oil type, using a 4-ball machine according to the ASTM D 2783 procedure.
- the lubricant formulation used consists of a 100 Neutral Solvent oil containing 3% of chlorine in the form of chlorinated paraffin, and 1% of sulfur in the form of sulfur additive of Example 2; the results obtained are collated in table 2 below.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8614576A FR2605328B1 (fr) | 1986-10-17 | 1986-10-17 | Compositions d'olefines polysulfurees, leur preparation et leur utilisation comme additifs pour lubrifiants. |
FR8614576 | 1986-10-17 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0271368A1 EP0271368A1 (fr) | 1988-06-15 |
EP0271368B1 true EP0271368B1 (fr) | 1990-05-23 |
Family
ID=9340010
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP87402252A Expired - Lifetime EP0271368B1 (fr) | 1986-10-17 | 1987-10-09 | Compositions d'oléfines polysulfurées, leur préparation et leur utilisation comme additifs pour lubrifiants |
Country Status (12)
Country | Link |
---|---|
US (1) | US4839069A (ja) |
EP (1) | EP0271368B1 (ja) |
JP (1) | JP2619654B2 (ja) |
CN (1) | CN87107001A (ja) |
AU (1) | AU600983B2 (ja) |
BR (1) | BR8705541A (ja) |
CA (1) | CA1299173C (ja) |
DE (1) | DE3762879D1 (ja) |
ES (1) | ES2016642B3 (ja) |
FR (1) | FR2605328B1 (ja) |
IN (1) | IN168668B (ja) |
MX (1) | MX172211B (ja) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4730034A (en) * | 1987-01-23 | 1988-03-08 | Phillips Petroleum Company | Recovering poly(arylene sulfide) oligomers from a poly(arylene sulfide) reaction mixture |
ES2021149B3 (es) * | 1987-05-27 | 1991-10-16 | Inst Francais Du Petrole | Composiciones de olefinas polisulforadas de contenido en azufre elevado y de muy debil contenido en cloro, su preparacion y su utilizacion como aditivos para lubrificantes. |
FR2624133B1 (fr) * | 1987-12-02 | 1990-09-14 | Inst Francais Du Petrole | Compositions d'olefines polysulfurees, leur preparation et leur utilisation comme additifs pour lubrifiants |
FR2627105B3 (fr) * | 1988-02-16 | 1990-06-08 | Inst Francais Du Petrole | Procede de presulfuration de catalyseur de traitement d'hydrocarbures |
US5116523A (en) * | 1988-06-23 | 1992-05-26 | Mobil Oil Corporation | Sulfide adducts of high viscosity index polyalphaolefins |
FR2636070B1 (fr) * | 1988-09-07 | 1994-05-06 | Institut Francais Petrole | Compositions d'olefines polysulfurees, leur preparation et leur utilisation comme additifs pour lubrifiants |
FR2650290B1 (fr) * | 1989-07-27 | 1994-02-11 | Institut Francais Petrole | Compositions polysulfurees de corps gras insatures? et/ou d'esters d'acides (poly) insatures, et eventuellement d'olefines, leur preparation et leur utilisation |
CA2021224A1 (en) * | 1989-08-03 | 1991-02-04 | Scott Anthony Culley | Sulfurized olefin polymers soluble in polyalphaolefin lubricant oils |
US5538651A (en) * | 1995-06-19 | 1996-07-23 | The Lubrizol Corporation | Additive to improve fluidity of oil solutions of sheared polymers |
DE112019005587T5 (de) | 2018-11-09 | 2021-09-30 | Dic Corporation | Schmierölzusammensetzung |
CN113430033A (zh) * | 2021-06-22 | 2021-09-24 | 苏州安美润滑科技有限公司 | 强力高速磨削加工用油及其制备方法 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2708199A (en) * | 1951-10-24 | 1955-05-10 | Continental Oil Co | Preparation of organic polysulfides |
US2744070A (en) * | 1952-12-22 | 1956-05-01 | Continental Oil Co | Soluble cutting oil |
US3022351A (en) * | 1957-03-07 | 1962-02-20 | Phillips Petroleum Co | Production of organic polysulfides |
US3471404A (en) * | 1967-03-06 | 1969-10-07 | Mobil Oil Corp | Lubricating compositions containing polysulfurized olefin |
US3663624A (en) * | 1969-10-27 | 1972-05-16 | Du Pont | Preparation of anhydrous alkali mercaptides |
US3925414A (en) * | 1974-03-22 | 1975-12-09 | Mobil Oil Corp | Reaction product of isobutylene, sulfur monohalide and alkali metal mercaptide |
US3873454A (en) * | 1974-03-22 | 1975-03-25 | Mobil Oil | Lubricant composition |
US3994979A (en) * | 1975-05-01 | 1976-11-30 | Phillips Petroleum Company | Disulfide process |
US4204969A (en) * | 1978-10-10 | 1980-05-27 | Edwin Cooper, Inc. | Lubricant composition containing sulfurized olefin extreme pressure additive |
US4563302A (en) * | 1983-12-01 | 1986-01-07 | Edwin Cooper, Inc. | Sulfurized olefin process |
DE3560285D1 (en) * | 1984-04-20 | 1987-07-30 | Inst Francais Du Petrole | Process for the preparation of polysulfurised olefins, products so obtained and their use as additives for lubricants |
FR2563231B1 (fr) * | 1984-04-20 | 1986-06-27 | Inst Francais Du Petrole | Procede de preparation d'olefines polysulfurees, les produits obtenus et leur utilisation comme additifs pour lubrifiants |
-
1986
- 1986-10-17 FR FR8614576A patent/FR2605328B1/fr not_active Expired
-
1987
- 1987-10-09 DE DE8787402252T patent/DE3762879D1/de not_active Expired - Fee Related
- 1987-10-09 EP EP87402252A patent/EP0271368B1/fr not_active Expired - Lifetime
- 1987-10-09 ES ES87402252T patent/ES2016642B3/es not_active Expired - Lifetime
- 1987-10-16 BR BR8705541A patent/BR8705541A/pt not_active IP Right Cessation
- 1987-10-16 MX MX026961A patent/MX172211B/es unknown
- 1987-10-16 CA CA000549481A patent/CA1299173C/fr not_active Expired - Fee Related
- 1987-10-16 JP JP62262568A patent/JP2619654B2/ja not_active Expired - Lifetime
- 1987-10-16 US US07/109,006 patent/US4839069A/en not_active Expired - Fee Related
- 1987-10-16 AU AU79868/87A patent/AU600983B2/en not_active Ceased
- 1987-10-17 CN CN198787107001A patent/CN87107001A/zh active Pending
- 1987-10-19 IN IN751/MAS/87A patent/IN168668B/en unknown
Also Published As
Publication number | Publication date |
---|---|
DE3762879D1 (de) | 1990-06-28 |
FR2605328A1 (fr) | 1988-04-22 |
US4839069A (en) | 1989-06-13 |
JP2619654B2 (ja) | 1997-06-11 |
BR8705541A (pt) | 1988-05-24 |
CN87107001A (zh) | 1988-04-27 |
AU600983B2 (en) | 1990-08-30 |
IN168668B (ja) | 1991-05-18 |
AU7986887A (en) | 1988-04-21 |
ES2016642B3 (es) | 1990-11-16 |
CA1299173C (fr) | 1992-04-21 |
EP0271368A1 (fr) | 1988-06-15 |
JPS63110289A (ja) | 1988-05-14 |
MX172211B (es) | 1993-12-07 |
FR2605328B1 (fr) | 1989-08-04 |
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