EP0588561A1 - Motorölzusammensetzungen mit niedrigem Phosphorgehalt und Additivzusammensetzungen - Google Patents
Motorölzusammensetzungen mit niedrigem Phosphorgehalt und Additivzusammensetzungen Download PDFInfo
- Publication number
- EP0588561A1 EP0588561A1 EP93307133A EP93307133A EP0588561A1 EP 0588561 A1 EP0588561 A1 EP 0588561A1 EP 93307133 A EP93307133 A EP 93307133A EP 93307133 A EP93307133 A EP 93307133A EP 0588561 A1 EP0588561 A1 EP 0588561A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- sulfur
- phenol derivative
- containing phenol
- low
- 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 31
- 239000000654 additive Substances 0.000 title claims description 20
- 230000000996 additive effect Effects 0.000 title claims description 6
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 title claims 2
- 239000010705 motor oil Substances 0.000 title abstract description 56
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 46
- 150000002989 phenols Chemical class 0.000 claims abstract description 36
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000011593 sulfur Substances 0.000 claims abstract description 34
- 229910052751 metal Inorganic materials 0.000 claims abstract description 26
- 239000002184 metal Substances 0.000 claims abstract description 26
- 239000003599 detergent Substances 0.000 claims abstract description 22
- 239000002270 dispersing agent Substances 0.000 claims abstract description 20
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 claims abstract description 16
- 239000002199 base oil Substances 0.000 claims abstract description 15
- UYQYTUYNNYZATF-UHFFFAOYSA-N 6-methyl-4,6-bis(octylsulfanylmethyl)cyclohexa-1,3-dien-1-ol Chemical compound CCCCCCCCSCC1=CC=C(O)C(C)(CSCCCCCCCC)C1 UYQYTUYNNYZATF-UHFFFAOYSA-N 0.000 claims abstract description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 5
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- -1 dithiocarbamate compound Chemical class 0.000 claims description 19
- 239000010687 lubricating oil Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000003921 oil Substances 0.000 claims description 12
- 239000012990 dithiocarbamate Substances 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- LMODBLQHQHXPEI-UHFFFAOYSA-N dibutylcarbamothioylsulfanylmethyl n,n-dibutylcarbamodithioate Chemical compound CCCCN(CCCC)C(=S)SCSC(=S)N(CCCC)CCCC LMODBLQHQHXPEI-UHFFFAOYSA-N 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 4
- 230000001050 lubricating effect Effects 0.000 claims description 4
- 238000002485 combustion reaction Methods 0.000 claims description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 43
- 239000003112 inhibitor Substances 0.000 description 16
- 230000003647 oxidation Effects 0.000 description 14
- 238000007254 oxidation reaction Methods 0.000 description 14
- 239000007789 gas Substances 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 239000002480 mineral oil Substances 0.000 description 7
- 230000006866 deterioration Effects 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 150000004659 dithiocarbamates Chemical class 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- 0 *c1cc(*)c(*)c(*)c1 Chemical compound *c1cc(*)c(*)c(*)c1 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052750 molybdenum Inorganic materials 0.000 description 4
- 239000011733 molybdenum Substances 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 239000003502 gasoline Substances 0.000 description 3
- LJKQIQSBHFNMDV-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-2,4-dien-6-ol Chemical class C1=CC=CC2(O)C1S2 LJKQIQSBHFNMDV-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007866 anti-wear additive Substances 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 2
- 239000000567 combustion gas Substances 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000002542 deteriorative effect Effects 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical class C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- XYRMLECORMNZEY-UHFFFAOYSA-B [Mo+4].[Mo+4].[Mo+4].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S Chemical compound [Mo+4].[Mo+4].[Mo+4].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S XYRMLECORMNZEY-UHFFFAOYSA-B 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- IYRDVAUFQZOLSB-UHFFFAOYSA-N copper iron Chemical compound [Fe].[Cu] IYRDVAUFQZOLSB-UHFFFAOYSA-N 0.000 description 1
- KGGZTXSNARMULX-UHFFFAOYSA-L copper;dicarbamodithioate Chemical compound [Cu+2].NC([S-])=S.NC([S-])=S KGGZTXSNARMULX-UHFFFAOYSA-L 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- HKOUMIFWHSIIBQ-UHFFFAOYSA-N dioctylcarbamothioylsulfanyl n,n-dioctylcarbamodithioate Chemical compound CCCCCCCCN(CCCCCCCC)C(=S)SSC(=S)N(CCCCCCCC)CCCCCCCC HKOUMIFWHSIIBQ-UHFFFAOYSA-N 0.000 description 1
- HDKVJYLPNIUCJJ-UHFFFAOYSA-N dipentylcarbamothioylsulfanyl n,n-dipentylcarbamodithioate Chemical compound CCCCCN(CCCCC)C(=S)SSC(=S)N(CCCCC)CCCCC HDKVJYLPNIUCJJ-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000005027 hydroxyaryl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001463 metal phosphate Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
- 150000002752 molybdenum compounds Chemical class 0.000 description 1
- KHYKFSXXGRUKRE-UHFFFAOYSA-J molybdenum(4+) tetracarbamodithioate Chemical compound C(N)([S-])=S.[Mo+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S KHYKFSXXGRUKRE-UHFFFAOYSA-J 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001195 polyisoprene 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
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- INNSFNJTGFCSRN-UHFFFAOYSA-N tridecyl 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCCCCCCOC(=O)CSCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 INNSFNJTGFCSRN-UHFFFAOYSA-N 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical compound [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 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
- 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
- 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
- C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
- C10M129/95—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
- 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
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
- C10M135/10—Sulfonic acids or derivatives 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
- C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
- C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the groups
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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
- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M135/24—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
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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
- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M135/26—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
- C10M2219/066—Thiocarbamic type compounds
- C10M2219/068—Thiocarbamate metal salts
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
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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
- 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
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/061—Esters derived from boron
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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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
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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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
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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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/12—Groups 6 or 16
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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
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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
- C10N2040/251—Alcohol-fuelled engines
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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
- C10N2040/255—Gasoline engines
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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
- C10N2040/255—Gasoline engines
- C10N2040/28—Rotary engines
Definitions
- This invention relates to improved lubricating oils having excellent characteristics in anti-wear, detergency, oxidation stability and viscosity-temperature correlation. Especially, this invention relates to an engine oil that is hardly deteriorated on contact with nitrogen oxide gas (NOx) and that can work stably for a long time.
- NOx nitrogen oxide gas
- Automobile spark ignition and diesel engines have valve train systems, including valves, cams and rocker arms, which present special lubrication concerns. It is extremely important that the engine oil protects these parts from wear. Further, it is important for engine oils to suppress the production of deposits in the engines. Such deposits are produced from non-combustibles and incomplete combustibles of hydrocarbon fuels (e.g., gasoline, diesel fuel oil) and by the deterioration of the engine oil employed.
- hydrocarbon fuels e.g., gasoline, diesel fuel oil
- Base oils use a mineral oil or a synthetic oil as a base oil.
- simple base oils alone do not provide the necessary properties to provide the necessary wear protection, deposit control, etc., required to protect internal combustion engines.
- base oils are formulated with various additives, for imparting auxiliary functions, such as ashless dispersants, metallic detergents (i.e., metal-containing detergents), antiwear agents, antioxidants (i.e., oxidation inhibitors), viscosity index improvers and the like to give a compounded oil (i.e., a lubricating oil composition).
- combustion gas produced in a gasoline engine or a diesel engine is mostly exhausted from the exhaust pipe as exhaust gas, but a portion of the combustion gas leaks through a gap between piston and cylinder to blow into the crankcase as blow-by gas.
- the blow-by gas contains nitrogen oxide gas (NO X ) of high concentration, it oxidizes and deteriorates an engine oil (crank case oil) charged in the crank case.
- the crank cases of the engines are apt to be made small. Therefore, the amount of the engine oil charged in such a small crank case is lowered and the relative amount of nitrogen oxide introduced into the crank case as blow-by gas per the amount of the charged engine oil is increased. Consequently, the deterioration of engine oil is apt to be promoted.
- the concentration of nitrogen oxide in blow-by gas is further increasing.
- U.S. Patent No. 3,236,770 discloses a lubricating oil having a dialkylthiocarbonate, and either a metal dialkyl dithiophosphate; a basic alkaline earth metal sulfonate; or a basic alkaline earth metal alkyl phenol sulfide.
- U.S. Patent No. 3,240,705 discloses a 2,2'-trithiobis-(4-halo-6-alkylphenol).
- U.S. Patent No. 4,302,683 discloses an organo-molybdenum complex prepared by reacting a hydrocarbyl substituted thio-bis-phenol with a molybdenum source.
- U.S. Patent No. 4,764,294 discloses an engine oil having a base oil, a metal phosphate, a metal carbamate, and a para alkyl hydroxy-aryl sulfide.
- dithiocarbamates in lubricating oils is well known in the art.
- U.S. Patent No. 3,876,550 discloses lubricating compositions containing an alkylene bis(dithiocarbamate), as an antioxidant, and a substituted succinic acid as a rust inhibitor.
- the alkylene dithiocarbamate is represented in the patent by the formula R 1 R 2 N-C(S)-S-alkylene-S-C(S)-NR 3 R 4 .
- Example 5 of the patent describes a crankcase lubricant containing a viscosity improver, an ashless dispersant and methylene bis(dibutyldithiocarbamate).
- composition may also contain various other additives, for example, detergents, dispersants, viscosity improvers, extreme pressure agents, antiwear additives, etc., as well as other oxidation inhibitors and corrosion inhibitors and cites an extensive list of extreme pressure agents, corrosion inhibitors and antioxidants, including zinc salts of phosphorodithoic acid.
- additives for example, detergents, dispersants, viscosity improvers, extreme pressure agents, antiwear additives, etc.
- oxidation inhibitors and corrosion inhibitors include zinc salts of phosphorodithoic acid.
- U.S. Patent No. 4,879,054 is directed to cold temperature greases and teaches using dithiocarbamates such as Vanlube 7723, i.e., 4,4'-methylene bis(dithiocarbamate), in such greases to provide extreme pressure antiwear properties.
- dithiocarbamates such as Vanlube 7723, i.e., 4,4'-methylene bis(dithiocarbamate)
- Examples 13-18 describe using Vanlube 7723 and triarylphosphate as replacements for lead naphthenate and zinc dithiophosphate.
- dithiocarbamates as extreme pressure antiwear additives is also taught by U.S. Patent No. 4,859,352, and U.S. Patent No. 4,648,985 teaches that the combination of dithiocarbamates with zinc dithiophosphate and copper salts of carboxylic acid provide lubricants with extreme pressure properties.
- U.S. Patent No. 4,383,931 discloses using lubricating oils containing an oil-soluble molybdenyl bis- ⁇ -di- ketonate in combination with zinc dithiophosphate.
- Methylene bis(dihydrocarbyldithiocarbamates) are used as ashless antioxidants and extreme pressure agents.
- U.S. Patent No. 4,501,678 discloses using lubricating oils containing an alkyl thiocarbamoyl compound and either a molybdenum thiocarbamoyl compound or a molybdenum organophosphorodithioate.
- U.S. Patent No. 4,609,480 discloses using lubricating oils containing an alkyl thiocarbamoyl compound and a 1,3,4-thiadiazole compound.
- the oils can also contain, among other things, sulfurized oxymolydenum orga- nophosphorodithioates.
- the present invention provides a low-phosphorous lubricating oil composition that is hardly deteriorated on contact with nitrogen oxide gas (NO X ) and which can work stably for a long time.
- That composition has a major amount of a base oil of lubricating viscosity, from 0.5 to 20 wt.% of metal-containing detergent, from 0.1 to 3 wt.% of zinc dithiophosphate, from 0.5 to 15 wt.% of ashless dispersant, and from 0.05 to 5 wt.% of a sulfur-containing phenol derivative.
- the sulfur-containing phenol derivative is selected from the group consisting of: and wherein R 1 , R 2 , R 3 , and R 8 are the same or different and each represents an alkyl group of 1 to 18 carbon atoms; R 4 , R 5 , R 6 , and R 7 are the same or different and each represents an alkylene group of 1 to 3 carbon atoms; and R' represents an alkyl group of 1 to 4 carbon atoms.
- the sulfur-containing phenol derivative comprises 0.1 to 3 wt.% of the composition.
- the alkyl groups of the sulfur-containing phenol derivative should have 1-14 carbon atoms.
- Examples of preferred sulfur-containing phenol derivatives are 2,4-bis ⁇ (octylthio)methyl ⁇ -o-cresol, 2,2-thio-diethylenebis ⁇ 3-(3,5-di-t-butyl-4-hydroxyphenyl) propionate ⁇ , or tridecyl 2-(3,5-di-t-butyl-4-hydroxybenzylthio)acetate.
- the low-phosphorous lubricating oil composition also has from 0.05 to 8 wt.% of an alkylthiocarbamoyl compound represented by the formula: wherein R 9 , R 10 , R11 and R 12 are the same or different and each represents an alkyl group of 1-18 carbon atoms, and (X) represents S, S-S, S-CH 2 -S, S-CH 2 -CH 2 -S, S-CH 2 -CH 2 -CH 2 -S or S-CH 2 -CH(CH 3 )-S.
- R 9 , R 10 , R 11 and R 12 are independently selected from alkyl groups having 1 to 6 carbon atoms. More preferably, the dithiocarbamate compound is methylene bis(dibutyldithiocarbamate).
- the zinc dithiophosphate is a secondary alkyl type.
- This invention can further involve an additive concentrate having 100 weight parts of a metal-containing detergent, from 10 to 700 weight parts of an ashless dispersant, and from 2 to 200 weight parts of the sulfur-containing phenol derivative described above.
- NO X nitrogen oxide gas
- the present invention is an engine oil composition
- a base oil comprising a base oil, an ashless dispersant, a metal-containing detergent, zinc dithiophosphate and a sulfur- containing phenol derivative.
- sulfur-containing phenol derivative employed for the invention are the compounds represented by the following formulae (1), (2) and (3): and wherein R 1 , R 2 , R 3 and R 8 are the same or different and each represents an alkyl group of 1-18 carbon atoms; R 4 , R 5 , R 6 and R 7 are the same or different and each represents an alkylene group of 1-3 carbon atoms; and R' represents an alkyl group of 1 to 4 carbon atoms.
- the sulfur-containing phenol derivative of the formulae (I), (II) or (III) is dissolved or dispersed in a base oil together with various additives, such as metal-containing detergents, ashless dispersants, zinc dithiophosphate, viscosity index improvers and the like, in the same manner as known engine oil compositions (i.e., engine oils).
- metal-containing detergents ashless dispersants, zinc dithiophosphates, viscosity index improvers and base oils are known. These known materials or their analogous compounds can be employed for the preparation of the engine oil of the invention. Representative examples of these materials are described below.
- the base oil may be a mineral oil or synthetic oil or a blend of mineral oils and/or synthetic oils blended to give a base oil of the desired internal combustion engine oil viscosity.
- individually the oils used as its base oil will have a viscosity range of about from 10 to 120 cST at 40°C and will be selected or blended depending on the desired end use and the additives in the finished oil to give the desired grade of engine oil.
- the metal-containing detergent may be a metal phenate or a metal sulfonate.
- the metal phenate is an alkaline earth metal salt of sulfide of alkylphenol having an alkyl group of about 8-30 carbon atoms. Generally employed alkaline earth metals are calcium, magnesium and barium.
- the metal sulfonate is an alkaline earth metal salt of a sulfonated aromatic compound or a sulfonated mineral oil derived from lubricating oil having a molecular weight of about 400-600. Generally employed alkaline earth metals are also calcium, magnesium and barium.
- the metal phenate and metal sulfonate can be used singly or in combination.
- metal-containing detergents such as salicylate, phosphonate and naphthenate of alkaline earth metals. These detergents can be employed single or in combination. The aforementioned phenate and sulfonate can be employed in combination with these other metal-containing detergents.
- the metal-containing detergents may be of a neutral type or of an over-based type having an alkalinity value of 150-300 or more.
- the metal-containing detergent is generally incorporated into an engine oil in an amount of 0.5-20 wt.% per total amount of the engine oil.
- ashless dispersant used for the invention examples include succinimides, succinic esters, and benzylamine, each of which has an alkyl or alkenyl group of a molecular weight of about 700-3,000. In addition to these compounds, their derivatives (e.g., borated derivatives) are also employable.
- the ashless dispersant is generally incorporated into an engine oil in an amount of 0.5-15 wt.% per total amount of the engine oil.
- the zinc dithiophosphate used as an anti-wear agent or an oxidation inhibitor, generally is zinc dihydrocarbyl-dithiophosphate having an alkyl group of 3-18 carbon atoms or an alkylaryl group having an alkyl group of 3-18 carbon atoms.
- This agent is generally incorporated into an engine oil in an amount of 0.1-3 wt.% per total amount of the engine oil.
- viscosity index improvers examples include poly-(alkyl methacrylate), ethylene-propylene copolymer, styrene-butadiene copolymer, and polyisoprene. Viscosity index improvers of dispersant type (having increased dispersancy) or multi-function type are also employed. These viscosity index improvers can be used singly or in combination.
- the amount of viscosity index improver to be incorporated into an engine oil varies with desired viscosity of the compounded engine oil, and generally in the range of 0.5-20 wt.% per total amount of the engine oil.
- the engine oil of the invention may contain various additional additives other than those described above, if desired.
- additional additives include known extreme pressure agents, corrosion inhibitors, rust inhibitors, friction modifiers, anti-foaming agents and pour point depressants.
- other oxidation inhibitors e.g., hindered phenol
- anti-wear agents e.g., organic molybdenum compounds such as molybdenum dithiophosphate
- multi-functional additives e.g., organic molybdenum compounds such as molybdenum dithiophosphate
- the sulfur-containing phenol derivative preferably used for the invention is a compound represented by one of the following formulae (I), (11), and (III): and wherein R 1 , R 2 , R 3 and R 8 are the same or different and each represents an alkyl group of 1-18 carbon atoms; R 4 , R 5 , R 6 , and R 7 are the same or different and each represents an alkylene group of 1-3 carbon atoms; and R' represents an alkyl group of 1 to 4 carbon atoms.
- the alkyl groups in the above formulae may be of straight chain type or branched chain type. Examples of them include methyl, ethyl, propyl, n-butyl, isobutyl, pentyl, isopentyl group, heptyl group, octyl group, 2-ethylhexyl, nonyl, decyl, dodecyl and tridecyl. Particularly preferred are alkyl groups having 1-14 carbon atoms. Examples of the alkylene group in the formulae are methylene, ethylene and propylene.
- Each of the sulfur-containing phenol derivatives of the formulae (I), (11), and (III) can be used singly or in combination with other sulfur-containing phenol derivatives.
- the sulfur-containing phenol derivative of the formula (I) is used in combination with the sulfur-containing phenols derivative of formulae (II) or (III).
- the sulfur-containing phenol derivative is generally incorporated into an engine oil in an amount of 0.05 to 5 wt.%, preferably 0.1 to 3 wt.%, per total amount of the engine oil.
- the sulfur-containing phenol derivative is used in combination with a dithiophosphate such as zinc dialkyldithiophosphate or zinc dihydrocarbyldithiophosphate, which are known oxidation inhibitors for engine oils.
- a dithiophosphate such as zinc dialkyldithiophosphate or zinc dihydrocarbyldithiophosphate, which are known oxidation inhibitors for engine oils.
- the engine oil composition of the invention further contains an alkylthiocarbamoyl compound represented by the following formula: wherein R 9 , R 10 , R11 and R 12 are the same or different and each represents an alkyl group of 1-18 carbon atoms, and (X) represents S, S-S, S-CH 2 -S, S-CH 2 -CH 2 -S, S-CH 2 -CH 2 -CH 2 -S or S-CH 2 -CH(CH 3 )-S.
- R 9 , R 10 , R11 and R 12 are the same or different and each represents an alkyl group of 1-18 carbon atoms
- (X) represents S, S-S, S-CH 2 -S, S-CH 2 -CH 2 -S, S-CH 2 -CH 2 -CH 2 -S or S-CH 2 -CH(CH 3 )-S.
- the alkylthiocarbamoyl compounds of the above formula are known compounds, which are employed as a vulcanization accelerator or an additive of gear oils and turbine oils.
- the alkyl group in this formula may be of straight chain type or branched chain type. Examples of the alkyl group are methyl, ethyl, propyl, n-butyl, isobutyl, pentyl, isopentyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, and dodecyl.
- Preferred are alkyl groups having 1-10 carbon atoms.
- alkylthiocarbamoyl compounds include methylene bis(dibutyl dithiocarbamate), bis(dimethylthiocarbamoyl)-monosulfide, bis(dimethylthiocarbamoyl)disulfide, bis(diamylthiocarbamoyl)disulfide, and bis(dioctylthiocarbamoyl)disulfide.
- metal dithiocarbamates such as zinc dithiocarbamate, copper dithiocarbamate and molybdenum dithiocarbamate are also employable. These compounds can be used singly or in combination of two or more compounds.
- the alkylthiocarbamoyl compound is generally incorporated into an engine oil in an amount of 0.05-8 wt.%., preferably 0.1-4 wt.%, per total amount of the engine oil.
- Various engine oils set forth in Table 1 were prepared from the same components such as paraffinic mineral oil (viscosity index value: 100), viscosity index improver and additives package (i.e., a mineral oil in which the same ashless dispersant, metal- containing detergent and zinc dialkyldithiophosphate are dissolved), and various additives set forth in Table 1.
- the viscosity of each prepared engine oil was adjusted to SAE 10W30.
- the engine oil was periodically sampled and charged in an optical cell of 0.1 mm thickness to measure IR absorption spectrum.
- the amount of nitrate ester formed in the sampled oil was evaluated by the absorbance at 1630 cm- 1 .
- the lifetime of the sampled engine oil was determined by the time when the absorbance was reached to 0.2.
- paraffinic mineral oil (viscosity index value: 100) was used for the engine oils set forth in Table 1 as a base oil, and each of the engine oils was prepared to satisfy the viscosity condition regulated in SAE 10W30 of API service. Further, other supplemental additives such as anti-foaming agents were added when they were required. Details of the additives set forth in Table 1 are as follows:
- each of the engine oils of the present invention i.e., the engine oils of No. 4 - No. 8
- the sulfur-containing phenol derivative had been added
- the engine oils of No. 7 and No. 8 in which the sulfur-containing phenol derivative had been incorporated with an alkylthiocarbamoyl compound, exhibited longer lifetimes than others.
- the engine oil composition of the present invention which is prepared by incorporating a sulfur-containing phenol derivative to a composition of a lubricating base oil, an ashless dispersant, a metal-containing detergent and zinc dithiophosphate, is hardly deteriorated on contact with nitrogen oxide (NO X ) gas of high concentration and can work stably for a long time.
- NO X nitrogen oxide
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Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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US113868 | 1987-10-27 | ||
JP272424/92 | 1992-09-14 | ||
JP4272424A JPH0693281A (ja) | 1992-09-14 | 1992-09-14 | エンジン油組成物 |
US08/113,868 US5569405A (en) | 1992-09-14 | 1993-08-27 | Low phosphorous engine oil compositions and additive compositions |
Publications (2)
Publication Number | Publication Date |
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EP0588561A1 true EP0588561A1 (de) | 1994-03-23 |
EP0588561B1 EP0588561B1 (de) | 1998-12-02 |
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EP93307133A Expired - Lifetime EP0588561B1 (de) | 1992-09-14 | 1993-09-09 | Motorölzusammensetzungen mit niedrigem Phosphorgehalt und Additivzusammensetzungen |
Country Status (3)
Country | Link |
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EP (1) | EP0588561B1 (de) |
DE (1) | DE69322344T2 (de) |
SG (1) | SG48102A1 (de) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
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WO1996006904A1 (en) * | 1994-09-01 | 1996-03-07 | Tonen Corporation | Lubricants with sustained fuel economy performance |
EP0816477A1 (de) * | 1995-03-14 | 1998-01-07 | Idemitsu Kosan Company Limited | Motorölzusammensetzung für brennkraftmaschinen |
EP1006173A1 (de) * | 1998-11-30 | 2000-06-07 | Ethyl Petroleum Additives Limited | Schmierölzusammensetzungen mit erhöhter Stabilität |
EP1104800A2 (de) * | 1999-12-02 | 2001-06-06 | Oronite Japan Limited | Schmiermittelzusammensetzung für Gasmotoren |
US6326336B1 (en) | 1998-10-16 | 2001-12-04 | Ethyl Corporation | Turbine oils with excellent high temperature oxidative stability |
WO2005026301A1 (en) * | 2003-09-05 | 2005-03-24 | Exxonmobil Research And Engineering Company | Long life lubricating oil composition using particular antioxidant components |
EP2692840A1 (de) * | 2012-07-31 | 2014-02-05 | Infineum International Limited | Schmierölzusammensetzung |
CN115678646A (zh) * | 2022-08-05 | 2023-02-03 | 黎光泰富(苏州)科技有限公司 | 一种超低温启动性能的柴油机油 |
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US3876550A (en) * | 1974-04-15 | 1975-04-08 | Lubrizol Corp | Lubricant compositions |
US3923669A (en) * | 1974-10-31 | 1975-12-02 | Sun Oil Co Pennsylvania | Antiwear hydraulic oil |
GB1569433A (en) * | 1978-05-16 | 1980-06-18 | Ciba Geigy Ag | Lubricant compositions |
EP0059168A1 (de) * | 1981-02-19 | 1982-09-01 | Ciba-Geigy Ag | Organische Elastomere und mineralische und synthetische Schmieröle, enthaltend Phenol-mercaptocarbonsäureester als Stabilisatoren |
US4394276A (en) * | 1981-10-26 | 1983-07-19 | Chevron Research Company | Method for improving fuel economy of internal combustion engines using sulfur-containing alkanediols |
EP0224442A1 (de) * | 1985-11-13 | 1987-06-03 | Ciba-Geigy Ag | Substituierte Phenole als Stabilisatoren |
EP0281992A2 (de) * | 1987-03-12 | 1988-09-14 | Idemitsu Kosan Company Limited | Schmierölgemische und ein Zusatz für Schmieröl |
EP0346283A2 (de) * | 1988-06-09 | 1989-12-13 | Ciba-Geigy Ag | Schmierölzusammensetzung |
EP0480734A1 (de) * | 1990-10-11 | 1992-04-15 | The Lubrizol Corporation | Antioxydationsmittel |
EP0528610A1 (de) * | 1991-08-09 | 1993-02-24 | Oronite Japan Limited | Motorölzusammensetzung mit niedrigem Phosphongehalt und Additivzusammensetzungen |
-
1993
- 1993-09-09 DE DE69322344T patent/DE69322344T2/de not_active Expired - Lifetime
- 1993-09-09 SG SG1996007046A patent/SG48102A1/en unknown
- 1993-09-09 EP EP93307133A patent/EP0588561B1/de not_active Expired - Lifetime
Patent Citations (10)
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US3876550A (en) * | 1974-04-15 | 1975-04-08 | Lubrizol Corp | Lubricant compositions |
US3923669A (en) * | 1974-10-31 | 1975-12-02 | Sun Oil Co Pennsylvania | Antiwear hydraulic oil |
GB1569433A (en) * | 1978-05-16 | 1980-06-18 | Ciba Geigy Ag | Lubricant compositions |
EP0059168A1 (de) * | 1981-02-19 | 1982-09-01 | Ciba-Geigy Ag | Organische Elastomere und mineralische und synthetische Schmieröle, enthaltend Phenol-mercaptocarbonsäureester als Stabilisatoren |
US4394276A (en) * | 1981-10-26 | 1983-07-19 | Chevron Research Company | Method for improving fuel economy of internal combustion engines using sulfur-containing alkanediols |
EP0224442A1 (de) * | 1985-11-13 | 1987-06-03 | Ciba-Geigy Ag | Substituierte Phenole als Stabilisatoren |
EP0281992A2 (de) * | 1987-03-12 | 1988-09-14 | Idemitsu Kosan Company Limited | Schmierölgemische und ein Zusatz für Schmieröl |
EP0346283A2 (de) * | 1988-06-09 | 1989-12-13 | Ciba-Geigy Ag | Schmierölzusammensetzung |
EP0480734A1 (de) * | 1990-10-11 | 1992-04-15 | The Lubrizol Corporation | Antioxydationsmittel |
EP0528610A1 (de) * | 1991-08-09 | 1993-02-24 | Oronite Japan Limited | Motorölzusammensetzung mit niedrigem Phosphongehalt und Additivzusammensetzungen |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996006904A1 (en) * | 1994-09-01 | 1996-03-07 | Tonen Corporation | Lubricants with sustained fuel economy performance |
EP0816477A1 (de) * | 1995-03-14 | 1998-01-07 | Idemitsu Kosan Company Limited | Motorölzusammensetzung für brennkraftmaschinen |
EP0816477B1 (de) * | 1995-03-14 | 2001-06-13 | Idemitsu Kosan Company Limited | Motorölzusammensetzung für brennkraftmaschinen |
US6326336B1 (en) | 1998-10-16 | 2001-12-04 | Ethyl Corporation | Turbine oils with excellent high temperature oxidative stability |
EP1006173A1 (de) * | 1998-11-30 | 2000-06-07 | Ethyl Petroleum Additives Limited | Schmierölzusammensetzungen mit erhöhter Stabilität |
EP1104800A2 (de) * | 1999-12-02 | 2001-06-06 | Oronite Japan Limited | Schmiermittelzusammensetzung für Gasmotoren |
EP1104800A3 (de) * | 1999-12-02 | 2001-06-20 | Oronite Japan Limited | Schmiermittelzusammensetzung für Gasmotoren |
SG97992A1 (en) * | 1999-12-02 | 2003-08-20 | Oronite Japan Ltd | Lubricating oil composition for gas engines |
WO2005026301A1 (en) * | 2003-09-05 | 2005-03-24 | Exxonmobil Research And Engineering Company | Long life lubricating oil composition using particular antioxidant components |
EP2692840A1 (de) * | 2012-07-31 | 2014-02-05 | Infineum International Limited | Schmierölzusammensetzung |
JP2014031514A (ja) * | 2012-07-31 | 2014-02-20 | Infineum Internatl Ltd | 潤滑油組成物 |
US9080126B2 (en) | 2012-07-31 | 2015-07-14 | Infineum International Limited | Lubricating oil composition |
CN115678646A (zh) * | 2022-08-05 | 2023-02-03 | 黎光泰富(苏州)科技有限公司 | 一种超低温启动性能的柴油机油 |
Also Published As
Publication number | Publication date |
---|---|
DE69322344T2 (de) | 1999-04-29 |
EP0588561B1 (de) | 1998-12-02 |
DE69322344D1 (de) | 1999-01-14 |
SG48102A1 (en) | 1998-04-17 |
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