US3775321A - Lubricating oil composition - Google Patents
Lubricating oil composition Download PDFInfo
- Publication number
- US3775321A US3775321A US00161947A US3775321DA US3775321A US 3775321 A US3775321 A US 3775321A US 00161947 A US00161947 A US 00161947A US 3775321D A US3775321D A US 3775321DA US 3775321 A US3775321 A US 3775321A
- Authority
- US
- United States
- Prior art keywords
- present
- composition
- compositions
- carbon atoms
- chlorinated
- 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 abstract description 158
- 239000010687 lubricating oil Substances 0.000 title description 40
- 150000001875 compounds Chemical class 0.000 abstract description 31
- 230000003647 oxidation Effects 0.000 abstract description 24
- 238000007254 oxidation reaction Methods 0.000 abstract description 24
- 150000004985 diamines Chemical class 0.000 abstract description 23
- 229910052709 silver Inorganic materials 0.000 abstract description 20
- 239000004332 silver Substances 0.000 abstract description 20
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract description 19
- 230000001050 lubricating effect Effects 0.000 abstract description 18
- 150000001342 alkaline earth metals Chemical class 0.000 abstract description 10
- 230000006866 deterioration Effects 0.000 abstract description 8
- 238000002485 combustion reaction Methods 0.000 abstract description 7
- 238000005461 lubrication Methods 0.000 abstract description 4
- 150000005002 naphthylamines Chemical class 0.000 abstract description 3
- -1 hydrocarbon radical Chemical class 0.000 description 63
- 125000004432 carbon atom Chemical group C* 0.000 description 47
- 229930195733 hydrocarbon Natural products 0.000 description 37
- 239000004215 Carbon black (E152) Substances 0.000 description 35
- 239000003599 detergent Substances 0.000 description 32
- 239000003921 oil Substances 0.000 description 29
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 19
- 239000011593 sulfur Substances 0.000 description 18
- 229910052717 sulfur Inorganic materials 0.000 description 18
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 16
- 229910000906 Bronze Inorganic materials 0.000 description 15
- 239000010974 bronze Substances 0.000 description 15
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 13
- 150000002430 hydrocarbons Chemical class 0.000 description 12
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 12
- 229910052791 calcium Inorganic materials 0.000 description 11
- 239000011575 calcium Substances 0.000 description 11
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002480 mineral oil Substances 0.000 description 8
- 150000003460 sulfonic acids Chemical class 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 235000010446 mineral oil Nutrition 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229920000098 polyolefin Polymers 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000002199 base oil Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- ZMRQTIAUOLVKOX-UHFFFAOYSA-L calcium;diphenoxide Chemical compound [Ca+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 ZMRQTIAUOLVKOX-UHFFFAOYSA-L 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 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 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 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 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 231100000241 scar Toxicity 0.000 description 3
- 150000003871 sulfonates Chemical class 0.000 description 3
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical class CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000002939 deleterious 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
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000010705 motor oil Substances 0.000 description 2
- YZZTZUHVGICSCS-UHFFFAOYSA-N n-butan-2-yl-4-[[4-(butan-2-ylamino)phenyl]methyl]aniline Chemical compound C1=CC(NC(C)CC)=CC=C1CC1=CC=C(NC(C)CC)C=C1 YZZTZUHVGICSCS-UHFFFAOYSA-N 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
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 239000010913 used oil Substances 0.000 description 2
- 210000000707 wrist Anatomy 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- FCTALLDRCBVIQN-UHFFFAOYSA-N 1,1'-biphenyl;naphthalen-1-amine Chemical class C1=CC=C2C(N)=CC=CC2=C1.C1=CC=CC=C1C1=CC=CC=C1 FCTALLDRCBVIQN-UHFFFAOYSA-N 0.000 description 1
- YCXSPKZLGCFDKS-UHFFFAOYSA-N 1-dodecylcyclohexane-1-sulfonic acid Chemical class CCCCCCCCCCCCC1(S(O)(=O)=O)CCCCC1 YCXSPKZLGCFDKS-UHFFFAOYSA-N 0.000 description 1
- ZRMMVODKVLXCBB-UHFFFAOYSA-N 1-n-cyclohexyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1CCCCC1NC(C=C1)=CC=C1NC1=CC=CC=C1 ZRMMVODKVLXCBB-UHFFFAOYSA-N 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical class CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- IXKVYSRDIVLASR-UHFFFAOYSA-N 2,3-dioctylphenol Chemical class CCCCCCCCC1=CC=CC(O)=C1CCCCCCCC IXKVYSRDIVLASR-UHFFFAOYSA-N 0.000 description 1
- HMWIHOZPGQRZLR-UHFFFAOYSA-N 2-hexadecylphenol Chemical class CCCCCCCCCCCCCCCCC1=CC=CC=C1O HMWIHOZPGQRZLR-UHFFFAOYSA-N 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical class CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
- JOONSONEBWTBLT-UHFFFAOYSA-N 2-tetradecylphenol Chemical class CCCCCCCCCCCCCCC1=CC=CC=C1O JOONSONEBWTBLT-UHFFFAOYSA-N 0.000 description 1
- OREKREJVUNVFJP-UHFFFAOYSA-N 2-triacontylphenol Chemical class CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1=CC=CC=C1O OREKREJVUNVFJP-UHFFFAOYSA-N 0.000 description 1
- CTTVKXMURPTCOF-UHFFFAOYSA-N 4-[2-[4-(dimethylamino)phenyl]propan-2-yl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C)(C)C1=CC=C(N(C)C)C=C1 CTTVKXMURPTCOF-UHFFFAOYSA-N 0.000 description 1
- KZNDXCVEWRZEEU-UHFFFAOYSA-N 4-n-cyclohexyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC=CC=1)C1CCCCC1 KZNDXCVEWRZEEU-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical class C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Chemical class CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical class OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 230000002708 enhancing effect Effects 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
- 239000000446 fuel Substances 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001802 myricyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VIVZTUCNTFHGLE-UHFFFAOYSA-N n-dodecyl-n-phenylnaphthalen-1-amine Chemical class C=1C=CC2=CC=CC=C2C=1N(CCCCCCCCCCCC)C1=CC=CC=C1 VIVZTUCNTFHGLE-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000005608 naphthenic acid group Chemical group 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M141/08—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 sulfur-, selenium- or tellurium-containing compound
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2219/106—Thiadiazoles
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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
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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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
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
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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
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
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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
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
- C10M2225/041—Hydrocarbon polymers
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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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/02—Unspecified siloxanes; Silicones
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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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
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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
- C10N2040/135—Steam engines or turbines
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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 new and improved lubricating oil compositions. More particularly, it releates to lubricating oil compositions which exhibit improved wear resistance toward metals such as both silver and bronze. The invention also relates to lubricating compositions having improved resistance to deterioration by oxidation.
- Mineral oil lubricating compositions which are used in severe service, for example, as lubricants for railroad diesel engines, are advantageously alkaline in nature.
- the alkalinity is desired to neutralize certain acids which are formed in the engine during operation.
- Typical among the conventional sources of alkalinity are the normal alkali metal and alkaline earth metal phenates.
- the incorporation of these phenates and other additives into engine lubricants can cause excessive wear in silver engine components such as, for example, silver wrist pin bushings in railroad engines and the silver bearing surfaces in aircraft engines.
- one of the objects of the present invention is to provide a lubricating oil composition which imparts improved wear properties to engine components of metals such as silver, bronze and the'like.
- Another object of the present invention is to provide a lubricating oil composition having improved resistance toward deterioration by oxidation. Other objects and advantages of the present invention will become apparent hereinafter.
- the present invention is a lubricating oil composition which comprises a major proportion of oil of lubricating viscosity; a minor amount of a least one phenate selected from the group consisting of alkali metal phenate, alkaline earth metal phenate and mixtures thereof, said phenate being present in an amount 3,775,321 Patented Nov.
- At least one chlorinated hydrocarbonaceous component which comprises at least about 5%, preferably at least about 20%, by weight of chlorine, said chlorinated hydrocarbonaceous component being present in an amount sufficient to improve the wear properties of said lubricating oil composition toward bronze; at least one sulfur-containing compound having the following structure:
- each R is a monovalent hydrocarbon radical containing from 1 to about 30 carbon atoms, at and y each are integers from 1 to 9, the sum of x and y being at least 2, said sulfur-containing compound being present in an amount sufiicient to improve the wear properties of said lubricating oil composition toward silver; at least one naphthyl amine having the following structure:
- R is selected from the group consisting of hydrogen and monovalent hydrocarbon radicals containing from 1 to about 30, preferably from about 6 to about 18 carbon atoms, a is an integer from zero to 7, preferably zero to 1 inclusive and D is a monovalent hydrocarbon radical containing from 1 to about 30, preferably from about 1 to about 18 carbon atoms; at least one diamine component having the following structure:
- R R R and R are independently selected from the group consisting of hydrogen, alkyl having from 1 to about 12 carbon atoms, and aryl, aralkyl, alkaryl having from 6 to about 22 carbon atoms
- B is selected from the group consisting of divalent aromaticcontaining hydrocarbon radicals and substituted divalent aromatic-containing hydrocarbon radicals containing 6 to about 30, preferably from about 6 to about 24, carbon atoms, said naphthyl amine and diamine component each being present in an amount sufiicient to improve the resistance to oxidation of said lubricating oil composition.
- the phenate (expressed in terms of active ingredients) be present in an amount from about 1% to about 10%, more preferably from about 2% to about 7%, by weight of the total compositions.
- the preferred concentration of the chlorinated hydrocarbonaceous component is from about 0.05% to about 2.0%, more preferably from about 0.05% to about 0.5%, by weight of the total composition.
- the preferred concentration of the sulfur-containing compound is from about 0.02% to about 10%, more preferably from about 0.05 to about 2.0%, by weight of the total composition.
- the incorporation of a combination of at least one naphthyl amine and diamine component into a lubricating oil composition provides the lubricating oil composition with outstanding resistance to deterioration by oxidation.
- the naphthyl amine be present in a concentration of at least about 0.05 more preferably at least about 0.10%, by weight of the total composition.
- the naphthyl amine be present in a 3 concentration from about 0.05% to about 2.0%, more preferably from about 0.1% to about 1.0%, by weight of the total composition.
- the concentration of the diamine component is preferably at least about 0.01% by weight of the total composition.
- the diamine component concentration is preferably within the range from about 0.01% to about 2%, more preferably from about 0.01% to about 0.5%, by weight of the total composition.
- the base oils used in the compositions of the present invention are those conventionally used in lubricant manufacture.
- suitable lubricating oils include those having a viscosity within the range of about 50 SUS to about 2000 SUS, preferably from about 500 SUS to about 1200 SUS, at 100 F. These oils may be refined or otherwise processed to produce the desired quality.
- mineral oils are preferred the base oil may be synthetic in nature.
- a specific example of the oils used in the prsent invention is a mineral oil mixture having a viscosity of about 900 SUS at 100 F. Combinations or mixtures of two or more different base oils in a single lubricating composition are often used to provide the desired physical properties and these mixtures are, therefore, within the scope of the present invention.
- the base oil comprises a major portion, preferably at least about 70%, still more preferably at least about 85%, by weight of the total composition.
- the alkali metal and alkaline earth metal phenates which can be incorporated into the compositions of the present invention may be monomeric or polymeric in nature, with the polymeric phenates being preferred.
- the phenate may be polymerized, for example, by reaction with elemental sulfur to form sulfurized phenates.
- Other polyphenates, for example, carbon bridged polyphenates, are also suitable for use in the present invention.
- sulfurized phenates containing only mono-sulfide linkages be used when these phenates are used to contribute alkalinity to the compositions of the present invention.
- the preferred phenates for use in the present invention are the alkaline earth metal, more preferably calcium, phenates.
- A is an essentially hydrocarbon aromatic radical, preferably a benzene radical
- R is a cyclic, straight-chained or branched-chained, saturated, essentially hydrocarbon radical having from 4 to 30 carbon atoms, represents oxygen
- b is an integer having a value of 1 to 5.
- hydrocarbon i.e., hydrocarbonaceous radical
- hydrocarbonaceous radical those radicals which are composed mainly of hydrogen and carbon, and include such radicals which contain, in addition, minor amounts of substituents,such as chlorine, bromine, oxygen, sulfur, nitrogen and the like, which do not substantially affect their hydrocarbon character.
- hydrocarbonaceous radicals examples include alkyl radicals such as butyl, hexyl, octyl, decyl, dodecyl, hexadecyl, eicosyl, triacontyl, etc.; radicals derived from petroleum hydrocarbons, such as white oil, wax, olefin polymers (e.g., polypropylene and polybutylene), etc.; aryl radicals such as phenyl, naphthyl, etc.; aralykyl radicals such as benzyl, phenylethyl, phenyloctyl, phenyldecyl, phenyloctadecyl, etc.; alkaryl radicals such as amylphenyl, octylphenyl, nonylphenyl, cetylphenyl,
- cyclic non-benzenoid radicals such as cyclohexyl, bornyl, etc.
- Examples of calcium phenates include the calcium salts of octyl phenol, nonyl phenol, dodecyl phenol, tetradecyl phenol, hexadecyl phenol, triacontyl phenol, dioctyl phenol, dinonyl phenol and the like.
- the chlorinated hydrocarbonaceous components sultable for use in the present invention may vary widely in structure and composition provided that the chlorine content of these components is at least about 5%, preferably at least about 20%, by weight.
- suitable chlorinated components include the chlorinated parafiins (including paraflin wax, kerosene and the like), chlorinated olefins and chlorinated polyolefins, chlorinated cycloaliphatic compounds, chlorinated aromatics (including chlorinated biphenyls and chlorinated naphthenes), chlorinated esters of fatty, naphthenic and resin acids and the like and mixtures thereof which contain less than about 70 carbon atoms per molecule.
- chlorinated component may be used in a single composition, and such a composition is within the scope of the present invention. It is preferred to use chlorinated parafiins, chlorinated olefins and polyolefins, chlorinated cycloaliphatic compounds, chlorinated esters of fatty, naphthenic and resin acids and mixtures thereof which contain less than about 70, preferably from about 10 to about 40 carbon atoms per molecule. Still more preferably, chlorinated parafiin containing from about 10 to about 40 carbon atoms per molecule can be used.
- the chlorinated components useful in the present invention may be prepared in any conventional manner, such as, for example, contacting molecular chlorine with the hydrocarbonaceous material to be chlorinated.
- hydrocarbonaceous material is meant those materials (e.g., parafiins, waxes, olefins, polyolefins and the like) which are composed mainly of hydrogen and carbon, and include such materials which contain, in addition, minor amounts of substituents, such as oxygen, sulfur, nitrogen, etc., which do not substantially alfect their hydrocarbon character.
- substituents such as oxygen, sulfur, nitrogen, etc.
- each R is the same or different monovalent hydrocarbon radicals, x and y each are integers from 1 to about 9 and the sum of x and y is at least 2, and preferably 4 to about 16.
- the radicals R can be aliphatic or aromatic including acyclic, alicyclic, aralkyl, aryl and alkaryl radicals and mixtures of such radicals.
- the hydrocarbon radicals can contain from 1 to about 30 car bon atoms, and preferably from about 1 to about 18 carbon atoms.
- the most preferred sulfur containing compounds are those in which each R is alkyl having from 1 to about 18 carbon atoms and x and y each are integers from 1 to 3.
- Suitable monovalent hydrocarbon radicals are ethyl, propyl, butyl, hexyl, octyl, nonyl, decyl, dodecyl, tridecyl, hexadecyl, octadecyl, cycle-hexyl, phenyl, tolyl, benzyl, naphthyl, styryl and the like.
- the sulfur-containing compound may be present in the compositions of the present invention in an amount sufficient to improve the wear properties of the composition toward silver.
- the preferred concentration of these sulfur-containing compounds is from about 0.02% to about 10.0%, more preferably from about 0.05% to about 2.0%, by weight of the total composition.
- the naphthyl aminessuitablefor use in the present invention comprise a broad class of: compounds.
- the general structural formula for these-compounds is "asfollows: a w
- R is selected from the group consisting of hy drogen and monovalent hydrocarbon radicals containing from 1 to about 30, preferably from about 6 to about 18 carbon atoms, a is aninteger from zero to 7, preferably zero to 1 inclusive, D is a monovalent hydrocarbon radical containing from 1 to about 30, preferably from about 1 to about 18 carbon atoms. Included among the monovalent hydrocarbon radicals contemplated by the present invention are, for example, a1kyl, aryl, aralkyl, alkaryl and substituted counterparts of these radicals.
- phenyl alphaor beta-naphthylamine octylphenyl alphaor beta-naphthylamine, alpha-alpha, alpha-beta or beta-beta dinaphthylamines, various phen'anthryl-anthryl-naphthylamines, xylyl naphthylamines, dodecyl phenyl naphthylamines, biphenyl naphthylamines and phenyl naphthylamines alkylated with olefins containing from about 8 to about 24 carbon atoms per molecule.
- olefins include pinene, a-methylstyrene, and the like.
- R is a radical selected from the group consisting of aryl and alka'ryl containing from 6 to about 18 carbon atoms; are of particular usefulness in the present invention and are, therefore, the more preferred class of compounds for use in the present invention.
- R and R be H, i.e., hydrogen.
- alkyl groups from which R R R and R may be selected include methyl, ethyl, isopropyl, sec-butyl, cyclohexyl, octyl, nonyl,.decyl and the like.
- Examples of the aryl, aralkyl and alkaryl groups from which R R R and R may be selected include phenyl, benzyl, phenyl ethyl, phenyl isopropyl, phenyl octyl, phenyl decyl, tolyl, isopropyl phenyl, octyl phenyl, decyl phenyl and the like.
- Examples of the divalent aromatic-containing hydrocarbon radicals from which B may be selected include phenylene, alkylene diphenylene and phenylene dialkylene wherein the alkylene groups contain from 1 to about 12 carbon atoms, and the like radicals. These divalent hydrocarbon radicals may be substituted with minor amounts of oxygen, sulfur and the like.
- Examples of the suitable substituted divalent aromatic-containing hydrocarbon radicals include divalent diphenyl ethers, and diphenyl sulfides and the like.
- the following diamine components are among thosepreferred: Bis-(N-sec-butyl-p -amino phenyl) methane, N-isopropyl-N'-phenyl-pphenylene diamine, N-cyclohexyl-N-phenyl-p-phenylene diamine, 2,2-bis (p-N,N-dimethylaminophenyl) propane and mixtures thereof.
- compositions of the present invention In order to improve the detergent qualities of the compositions of the present invention, it is preferred to inelude from about 0.1% toabout 10%, more preferably from about 0.1% to about by weight of at least one sulfonate selected from the group consisting of alkali metal sulfonate, alkaline earth metal sulfonate and mixtures thereof.
- the preferred sulfonates for use in the compositions of the present invention are the alkaline earth metal sulfonates, more preferably, the calcium sulfonates.
- Sulfonates derived from sulfonic acids having about 12 to about 200 carbon atoms per molecule are of particular usefulness in the present invention.
- sulfonic acids are monoand polyalkyl substituted naphthalene sulfonic acids, phenol sulfonic acids, diphenyl ether sulfonic acids, diphenyl ether disulfonic acids, diphenyl sulfide-sulfonic acids, ..di-naphthylsulfide-sulfonic acids, diphenyl amine-sulfonioacids, phenylnaphthylsulfide sulfonic acids, cycloaliphatic.
- sulfonic acids such as petroleum naphthene sulfonic acids, cetylcyclopentyl sulfonic acids, lauryl-cyclohexyl sulfonic acids, bis-(diisobutyl)- cyclohexyl sulfonic acids, monoand poly-wax substituted cyclohexyl sulfonic acids, etc..
- sulfonic acids With respect to the sulfonic acids, it is intended herein to employ the term petroleum sulfonic acids to cover all sulfonic acids which are derived at least in'part from petroleum sources. Additional examples of sulfonic acids and/or the alkali and alkaline earth metal salts thereof which can be employed as starting materials are disclosed in the following U.S.
- the components comprising the compositions of the present invention are available as solutions or mixtures in mineral oil or other solvent carriers.
- the proportion ratios given in this application refer to the active components rather than the mixtures or solutions.
- the lubricating compositions of the present invention include at least one detergent in addition to the phenates and sulfonates described above.
- Both the ash-containing detergents, such as the conventional metal based detergents, and the ashless detergents are suitable for use. However, it is preferred to use the ashless detergents in the compositions of the present invention.
- these detergents are included in the compositions of this invention, they comprise from about 1% to about 6% by weight of the total composition.
- the ashless detergents preferred for use are compounds which comprise an oil solubilizing tail and a polar detergent head.
- Many ashless detergents fitting this general description are known to the art and are commercially available.
- basic polyamines substituted with long chain hydrocarbons having from about 30 to about 250 carbon atoms to provide oleophilic character are suitable for use in the present invention.
- this type of ashless detergent include the polyamines-polyalkylene alkenyl succinimides in which the alkenyl group contains from about 30 to about 250 carbon atoms, the divalent alkylene radicals, which number from about 2 to about 6, each contain from about 1 to about 3 carbon atoms; and the N-dialkylaminoalkyl alkenyl succinimides in which the alkenyl group contains from about 30 to about 250 carbon atoms and the divalent alkylene radical along with the two alkyl radicals contain a total of less than about 10 carbon atoms. See French Pat. 1,265,085 and U.S. Pat. 3,018,291, which are hereby incorporated by reference into the present application.
- the required polarity may be supplied by groups containing, for example, oxygen, sulfur, phosphorous as well as nitrogen and mixtures thereof.
- an ashless detergent can be derived by reacting a hydrocarbon polymer containing from about 30 to about 250 carbon atoms with P S See U.S. Pat. 3,003,964; and British Pat. 815,810; also U.S. Pats. 3,256,189 and 3,256,194, which patents are hereby incorporated by reference into the present application. All of these suitable ashless detergents may be generally characterized as compounds comprising a hydrocarbon portion of sufficient size to render the compound oil soluble and at least one nonmetallic polar portion which provides a substantial part of the detergent action.
- lubricat ing oil compositions contemplated herein may contain other agents such as antifoam agents, corrosion inhibitors, metal deactivators, pour point depressants, oiliness agents, compounds for enhancing ,the;viscosity,index of the lubricating oil, etc.
- agents such as antifoam agents, corrosion inhibitors, metal deactivators, pour point depressants, oiliness agents, compounds for enhancing ,the;viscosity,index of the lubricating oil, etc.
- the lubricating oil compositionslofthe present invention can be used to lubricate internal combustion'engines, and in particular, engines having silver and/or bronze components, such as, for example, many railroad diesel engines. More specifically, the lubricating oil compositions of the present invention can be used to reduce the wear of metal, in particular, silver and bronze engine components which normally occurs during the operating of the engine. Maintaining .(or causing to be maintained) a lubricating amount of the oil compositions of the present invention on internal combustion engine components such as bearing surfaces, wrist pin bushings and the like requiring lubrication and/or wear improvement results in obtaining substantial benefifits from the present invention.
- compositions of the present invention which contain a combination of naphthyl amine and diamine components can be used to lubricate internal combustion engines in the manner noted above to give longer lubricant life because of the substantially improved oxidation resistance of these compositions.
- EXAMPLE 1 This example illustrates the deleterious effect that alkali and alkaline earth metal phenates may have on silver components of diesel engines.
- a lubricating oil composition was prepared by blending together individual components, noted below, at a slightly elevated temperature, i.e., from about 100 F. to about 130 F., to insure complete mixing.
- the final compositions were as follows.
- Component Weight percent Mineral oil, 890 SUS at 100 F. 89.7 Sulfurized calcium phenate 1 5.5 Ashless detergent 2 3.0 Calcium sulfonate 3 1.7
- the active material comprises monosulfide linked phenate derived from dodecyl phenol.
- the mixture has a total base number (ASTM Test D-664) of about 85.
- a mixture of about 50% by weight of detergent in a mineral carrier comprises, as an oil solubilizing portion, a hydrocarbon olefinpolymer which is believed to contain an average of about 75 to about 100 carbon atoms and, to provide a substantial part of the detergency action, a polar portion containing basic nitrogen.
- This detergent has a molecular weight of about 7860.
- This commercially available detergent mixture contains about 1.5% by weight of nibtrogein) and has a total base number of from about 30 to at out
- the calcium sulfonate is derived from petroleum sources and has about 25 carbon atoms per molecule.
- EMD engine bearing rating of the anti-wear properties of the lubricating oil are done on a numerical basis as prescribed by EMD with the following relationships.
- EMD silver bearing rating system 0-20 Excellent oil. 20-40 Good oil. 40-75 Borderline oil. 75 Failure.
- Silver bearing condition EMD rating 22 Surface condition Extensive pitting.
- EXAMPLE 2 Component: Weight percent Mineral oil, 890 SUS at F. 88.75 Sulfurized calcium phenate 6.0 Ashless detergent 3.0 Calcium sulfonate 1.7 Sulfur-containing compound 2 0.1
- composition contains about 0.001% by weight of Dow Corning silicon antifoaln agent.
- oxidation inhibitor i.e., the naphthyl amine or diamine component disclosed herein
- the improvement in oxidation resistance obtained by the composition containing a combination of additives is unexpectedly greater than the additive effect of each inhibitor alone.
- the preceding examples have demonstrated that the lubricating oil compositions of the present invention have improved wear properties toward both silver and bronze.
- these compositions can be used in an increased number of engines, for example, in engines which have silver components and/or bronze components.
- compositions of the present invention which contain a combination of oxidation inhibitors, have an unexpectedly high resistance to deterioration by oxidation.
- This discovery although quite distinct from the improved wear properties of the compositions of the present invention, is advan- 40 tageously used in conjunction with Wear resistant oil com- Weight percent of- Component
- This bench test procedure involves bubbling five liters of oxygen per hour through 300 ml. of test oil at 285 F. in the presence of a 1 in. by 3 in. steel backed copperlead specimen. Fifty ml. samples of the oil composition are withdrawn at 48 hour intervals with fresh oil being added to maintain a volume of 300 ml. The test is run for a total of 144 hours at which time the viscosity and percent n-pentane insolubles of the used oil are determined. Each of these determinations give an indication of the extent of oxidative deterioration experienced by the oil during thetest period. For example, both the viscosity increase of the test oil 'over the test period and the amount of n-pentane insolubles in the used oil are indications of for a longer useful lubricant life.
- a lubricating oil composition which comprises a major proportion of oil of lubricating viscosity; a minor amount of at least one phenate selected from the group consisting of alkali metal phenate, alkaline earth metal phenate and mixtures thereof, said phenate being present in an amount suflicient to contribute alkalinity to said lubricating oil composition; at least one chlorinated hydrocarbonaceous component which comprises at least about 5% by weight of chlorine, said chlorinated hydrocarbonaceous component being present in an amount sufiicient to improve the wear properties of said lubricating oil composition toward bronze; at least one sulfur containing compound having the following structure:
- each R is a monovalent hydrocarbon radical containing from 1'to about 30 carbon atoms, x and y are each integers from 1 to 9, the sum of x and y being at least 2, said sulfur containing compound being present in an amount sufficient to improve the wear properties of said lubricating oil composition toward silver; at least one naphthyl amine having the following structure:
- R is selected from the group consisting of hydrogen and monovalent hydrocarbon radicals containing from 1 to about 30 carbon atoms, a is an integer from zero to 7 and D is a monovalent hydrocarbon radical containing from 1 to about 30 carbon atoms; at least one diamine component having the following structure:
- R R R and R are independently selected from the group consisting of hydrogen, alkyl having from 1 to about 12 carbon atoms, and aryl, aralkyl, alkaryl having from 6 to about 22 carbon atoms
- B is selected from the group consisting of divalent aromatic-containing hydrocarbon radicals and substituted divalent aromaticcontaining hydrocarbon radicals containing from 6 to about 30 carbon atoms, said naphthyl amine and diamine component each being present in an amount sufficient to improve the resistance to oxidation of said lubricating oil composition.
- composition of claim 1 wherein said naphthyl amine is present in an amount of at least about 0.05% by weight of the total composition, said diamine component is present in an amount of at least 0.01% by weight of the total composition, R contains from about 6 to about 18 carbon atoms, a is an integer from to 1 inclusive, D contains from about 1 to 18 carbon atoms, and R and R are H.
- chlorinated hydrocarbonaceous component is selected from the group consisting of chlorinated parafiins, chlorinated olefins, chlorinated polyolefins, chlorinated cycloaliphatic compounds, chlorinated aromatics, chlorinated esters of fatty acids, chlorinated esters of naphthenic acids, chlorinated esters of resin acids and mixtures thereof, said chlorinated hydrocarbonaceous component containing less than about 70 carbon atoms per molecule.
- composition of claim 3 wherein said phenate is present in an amount from about 1% to about by weight of the total composition; said chlorinated hydrocarbonaceous component is present in an amount from about 0.05 to about 2.0% by weight of the total composition; and said sulfur-containing compound is present in an amount from about 0.02% to about 10.0% by weight of the total composition.
- composition of claim 4 wherein the chlorinated hydrocarbonaceous component comprises at least 20% by weight of chlorine.
- composition of claim 5 wherein said phenate is selected from the group consisting of alkaline earth metal phenate and mixtures thereof, said naphthyl amine is present in a concentration of from about 0.05 to about 2% by weight of the total composition, and said diamine component is present in a concentration from about 0.01% to about 2.0% by weight of the total composition.
- composition of claim 6 wherein R is a radical selected from the group consisting of aryl and alkaryl containing from 6 to about 18 carbon atoms and said diamine component is selected from the group consisting of bis-(N-sec-butyl-p-amino phenyl) methane, N-isopro- 12 pyl-N'-phenyl-p-phenylenediainine, N cyclohexyl-N'- phenyl-p-phenylene diamine, 2,2;bis (p-N,N' d im ethylaminophenyl) propane and'mixtures thereof.
- R is a radical selected from the group consisting of aryl and alkaryl containing from 6 to about 18 carbon atoms and said diamine component is selected from the group consisting of bis-(N-sec-butyl-p-amino phenyl) methane, N-isopro- 12 pyl-N'-phenyl-p-phenyl
- composition of claim 7 wherein said chlorinated hydrocarbonaceous component contains from about 10 to about 40 carbon atoms.
- composition of claim 8 wherein said phenate is selected from the group consisting of calcium phenate and mixtures thereof, said naphthyl amine is present in a concentration of from about 0.10% to about 1.0% by weight of the total composition and said diamine com-' ponent is present in a concentration of from about 0.01% to about 0.5% by weight of the total composition.
- a lubricating oil composition which comprises a major proportion of oil of lubricating viscosity; at least one naphthyl amine having the following structure:
- R is selected from the group consisting of hydrogen and monovalent hydrocarbon radicals containing from 1 to about 30 carbon atoms, ais an integer from zero to 7 and D is a monovalent hydrocarbon radical containing from 1 to about 30 carbon atoms; at least one diamine component having the following structure:
- R R R and R are independently selected from the group consisting of hydrogen, alkyl having from 1 to about 12 carbon atoms, and aryl, aralkyl, alkaryl having from 6 to about 22 carbon atoms
- B is selected from the group consisting of divalent aromatic-containing hydrocarbon radicals and substituted divalent aromaticcontaining hydrocarbon radicals containing from 6 to about 30 carbon atoms, said naphthyl amine and diamine component each being present in an amount sufiicient to improve the resistance to oxidation of said lubricating oil composition.
- composition of claim 10 wherein said naphthyl amine is present in an amount of at least about 0.05 by weight of the total composition, and said diamine component is present in an amount of at least about 0.01% by weight of the total composition.
- composition of claim 11 wherein R contains from about 6 to about 18 carbon atoms, a is an integer from 0 to 1 inclusive, D contains from about 1 to 18 carbon atoms and R and R are H.
- composition of claim 13 wherein said naphthyl amine is present in an amount from about 0.05% to about 2% by weight of the total composition and said diamine component is present in an amount from about 0.01% to about 2.0% by weight of the total composition.
- composition of claim 14 wherein said composition contains from about 1% to about 6% by weight of at least one ashless detergent, said ashless detergent being a compound which comprises a hydrocarbon portion of sufiicient size to render said compound oil soluble and at least one non-metallic polar portion which provides a substantial portion of the detergent action.
- composition of claim 4 wherein-said composition contains from about 1% to about 6% by weight of at least one ashless detergent, said ashless detergent being a compound which comprises a hydrocarbon portion of sufficient size to render said compound oil soluble and at least one non-metallic polar portion which provides a substantial portion of the detergent action.
- composition of claim 6 wherein said composition contains from about 1% to about 6% by weight of at least one ashless detergent, said ashless detergent being a compound which comprises a hydrocarbon portion of sufiicient size to render said compound oil soluble and at least one non-metallic polar portion which provides a substantial portion of the detergent action.
- composition of claim 9 wherein said composition contains from about 1% to about 6% by weight of at least one ashless detergent, said ashless detergent being a compound which comprises a hydrocarbon portion of sufiicient size to render said compound oil soluble and at least one non-metallic polar portion which provides a substantial portion of the detergent action.
- composition of claim 1 wherein said com position contains from about 0.1% to about 10% by weight of at least one sulfonate selected from the group consisting of alkali metal sulfonate, alkaline earth metal sulfonate and mixtures thereof, said sulfonate being present in an amount suflicient to improve the lubricating qualities of said composition.
- composition of claim 6 wherein saidcomposition contains from about 0.1% to about 5% by weight of at least one alkaline earth metal sulfonate, said sulfonate being present in an amount suflicient to improve the lubricating qualities of said composition.
- composition of claim 9 wherein said composition contains from about 0.1% to about 5% by weight of at least one calicum sulfonate, said sulfonate being present in an amount suflicient to improve the lubricating qualities of said composition.
- composition of claim 17 wherein said composition contains from 0.1% to about 5.0% by weight of at least one calcium sulfonate derived from a sulfonic acid having from about 12 to about 200 carbon atoms per molecule, said sulfonate being present in an amount suflicient to improve the lubricating qualities of said composition.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16194771A | 1971-07-09 | 1971-07-09 | |
| US401093A US3909420A (en) | 1971-07-09 | 1973-09-26 | Lubricant composition containing thiadiazoles and napthylamines as antioxidants and method of lubrication using said composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3775321A true US3775321A (en) | 1973-11-27 |
Family
ID=26858298
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00161947A Expired - Lifetime US3775321A (en) | 1971-07-09 | 1971-07-09 | Lubricating oil composition |
| US401093A Expired - Lifetime US3909420A (en) | 1971-07-09 | 1973-09-26 | Lubricant composition containing thiadiazoles and napthylamines as antioxidants and method of lubrication using said composition |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US401093A Expired - Lifetime US3909420A (en) | 1971-07-09 | 1973-09-26 | Lubricant composition containing thiadiazoles and napthylamines as antioxidants and method of lubrication using said composition |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US3775321A (cs) |
| CA (1) | CA983914A (cs) |
| FR (1) | FR2244813B1 (cs) |
| GB (2) | GB1401076A (cs) |
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3909420A (en) * | 1971-07-09 | 1975-09-30 | Atlantic Richfield Co | Lubricant composition containing thiadiazoles and napthylamines as antioxidants and method of lubrication using said composition |
| US3966623A (en) * | 1975-06-05 | 1976-06-29 | Texaco Inc. | Corrosion inhibited lube oil compositions |
| US3977986A (en) * | 1975-06-02 | 1976-08-31 | The United States Of America As Represented By The Secretary Of The Navy | Silicone-base fire resistant hydraulic fluid |
| US4086172A (en) * | 1976-04-01 | 1978-04-25 | Chevron Research Company | Lubricating oil additive composition |
| US4102796A (en) * | 1976-04-01 | 1978-07-25 | Chevron Research Company | Lubricating oil antioxidant additive composition |
| US4136043A (en) * | 1973-07-19 | 1979-01-23 | The Lubrizol Corporation | Homogeneous compositions prepared from dimercaptothiadiazoles |
| US4140643A (en) * | 1974-05-16 | 1979-02-20 | The Lubrizol Corporation | Nitrogen- and sulfur-containing lubricant additive compositions of improved compatibility |
| US4169799A (en) * | 1976-12-27 | 1979-10-02 | Texaco Inc. | Lubricating oil composition |
| US4171270A (en) * | 1976-12-27 | 1979-10-16 | Texaco Inc. | Sulfurized overbased calcium alkylphenolate lubricant composition |
| US4171269A (en) * | 1976-12-27 | 1979-10-16 | Texaco Inc. | Sulfurized lubricant composition |
| US4178253A (en) * | 1977-04-05 | 1979-12-11 | Ciba-Geigy Corporation | Corrosion inhibited lubricant compositions |
| US4216100A (en) * | 1978-08-03 | 1980-08-05 | Texaco Inc. | Pentaerythritol-fatty acid ester lubricant composition |
| US4534873A (en) * | 1983-09-28 | 1985-08-13 | Clark Gary G | Automotive friction reducing composition |
| US4770802A (en) * | 1986-02-04 | 1988-09-13 | Nippon Oil Co., Ltd. | Lubricating oil compositions |
| US4849118A (en) * | 1987-09-30 | 1989-07-18 | Amoco Corporation | Chlorine-free silver protective lubricant composition (III) |
| US5368758A (en) * | 1992-10-13 | 1994-11-29 | The Lubrizol Corporation | Lubricants, greases and aqueous fluids containing additives derived from dimercaptothiadiazoles |
| US5538652A (en) * | 1993-05-03 | 1996-07-23 | Mobil Oil Corporation | Dimercaptothiadiazole-mercaptan coupled compounds as multifunctional additives for lubricants and fuels |
| US5726133A (en) * | 1996-02-27 | 1998-03-10 | Exxon Research And Engineering Company | Low ash natural gas engine oil and additive system |
| US5801130A (en) * | 1995-12-22 | 1998-09-01 | Exxon Research And Engineering Company | High load-carrying turbo oils containing amine phosphate and dimercaptothiadiazole derivatives |
| US6207623B1 (en) | 2000-01-14 | 2001-03-27 | Exxonmobil Research And Engineering Company | Industrial oils of enhanced resistance to oxidation |
| US6248701B1 (en) * | 1994-05-13 | 2001-06-19 | Henkel Corporation | Aqueous metal coating composition and process with reduced staining and corrosion |
| EP1746148A1 (en) | 2005-07-20 | 2007-01-24 | Chevron Oronite Company LLC | Crankcase lubricating oil composition for protection of silver bearings in locomotive diesel engines. |
| WO2010024170A1 (ja) | 2008-08-29 | 2010-03-04 | 新日本石油株式会社 | 銀含有材料と接触する潤滑油組成物 |
| US8796192B2 (en) | 2010-10-29 | 2014-08-05 | Chevron Oronite Company Llc | Natural gas engine lubricating oil compositions |
| US8841243B2 (en) | 2010-03-31 | 2014-09-23 | Chevron Oronite Company Llc | Natural gas engine lubricating oil compositions |
| US8969273B2 (en) | 2009-02-18 | 2015-03-03 | Chevron Oronite Company Llc | Lubricating oil compositions |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4110234A (en) * | 1975-11-05 | 1978-08-29 | Uniroyal, Inc. | Antioxidant stabilized lubricating oils |
| US4122021A (en) * | 1977-05-16 | 1978-10-24 | Uniroyal, Inc. | Antioxidant stabilized lubricating oils |
| US4990273A (en) * | 1985-09-30 | 1991-02-05 | Union Oil Company Of California | Lubrication anti-wear additive |
| US5275630A (en) * | 1986-11-06 | 1994-01-04 | The Lubrizol Corporation | Metal salt fuel additive stabilized with a thiadiazole |
| JP2840526B2 (ja) * | 1993-06-24 | 1998-12-24 | 出光興産株式会社 | 潤滑油組成物 |
| WO1996006903A1 (en) * | 1994-08-31 | 1996-03-07 | Mobil Oil Corporation | Dimercaptothiadiazole-mercaptan coupled compounds as multifunctional additives for lubricants and fuels |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2009480A (en) * | 1932-06-10 | 1935-07-30 | Goodrich Co B F | Antioxidant |
| US2719126A (en) * | 1952-12-30 | 1955-09-27 | Standard Oil Co | Corrosion inhibitors and compositions containing same |
| US3236774A (en) * | 1962-08-10 | 1966-02-22 | Eastman Kodak Co | Antioxidant composition and synthetic lubricant containing it |
| US3513084A (en) * | 1968-06-28 | 1970-05-19 | Du Pont | Lubricant producing system |
| US3663561A (en) * | 1969-12-29 | 1972-05-16 | Standard Oil Co | 2-hydrocarbyldithio - 5 - mercapto-1,3,4-thiadiazoles and their preparation |
| US3775321A (en) * | 1971-07-09 | 1973-11-27 | Atlantic Richfield Co | Lubricating oil composition |
-
1971
- 1971-07-09 US US00161947A patent/US3775321A/en not_active Expired - Lifetime
-
1972
- 1972-06-19 CA CA145,063A patent/CA983914A/en not_active Expired
- 1972-06-23 GB GB2962472A patent/GB1401076A/en not_active Expired
-
1973
- 1973-09-26 US US401093A patent/US3909420A/en not_active Expired - Lifetime
-
1974
- 1974-09-24 FR FR7432158A patent/FR2244813B1/fr not_active Expired
- 1974-09-25 GB GB41738/74A patent/GB1480387A/en not_active Expired
Cited By (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3909420A (en) * | 1971-07-09 | 1975-09-30 | Atlantic Richfield Co | Lubricant composition containing thiadiazoles and napthylamines as antioxidants and method of lubrication using said composition |
| US4136043A (en) * | 1973-07-19 | 1979-01-23 | The Lubrizol Corporation | Homogeneous compositions prepared from dimercaptothiadiazoles |
| US4140643A (en) * | 1974-05-16 | 1979-02-20 | The Lubrizol Corporation | Nitrogen- and sulfur-containing lubricant additive compositions of improved compatibility |
| US3977986A (en) * | 1975-06-02 | 1976-08-31 | The United States Of America As Represented By The Secretary Of The Navy | Silicone-base fire resistant hydraulic fluid |
| US3966623A (en) * | 1975-06-05 | 1976-06-29 | Texaco Inc. | Corrosion inhibited lube oil compositions |
| US4086172A (en) * | 1976-04-01 | 1978-04-25 | Chevron Research Company | Lubricating oil additive composition |
| US4102796A (en) * | 1976-04-01 | 1978-07-25 | Chevron Research Company | Lubricating oil antioxidant additive composition |
| US4169799A (en) * | 1976-12-27 | 1979-10-02 | Texaco Inc. | Lubricating oil composition |
| US4171270A (en) * | 1976-12-27 | 1979-10-16 | Texaco Inc. | Sulfurized overbased calcium alkylphenolate lubricant composition |
| US4171269A (en) * | 1976-12-27 | 1979-10-16 | Texaco Inc. | Sulfurized lubricant composition |
| US4178253A (en) * | 1977-04-05 | 1979-12-11 | Ciba-Geigy Corporation | Corrosion inhibited lubricant compositions |
| US4216100A (en) * | 1978-08-03 | 1980-08-05 | Texaco Inc. | Pentaerythritol-fatty acid ester lubricant composition |
| US4534873A (en) * | 1983-09-28 | 1985-08-13 | Clark Gary G | Automotive friction reducing composition |
| US4770802A (en) * | 1986-02-04 | 1988-09-13 | Nippon Oil Co., Ltd. | Lubricating oil compositions |
| US4849118A (en) * | 1987-09-30 | 1989-07-18 | Amoco Corporation | Chlorine-free silver protective lubricant composition (III) |
| US5368758A (en) * | 1992-10-13 | 1994-11-29 | The Lubrizol Corporation | Lubricants, greases and aqueous fluids containing additives derived from dimercaptothiadiazoles |
| AU669390B2 (en) * | 1992-10-13 | 1996-06-06 | Lubrizol Corporation, The | Lubricants, greases, and aqueous fluids containing additives derived from dimercaptothiadiazoles |
| US5538652A (en) * | 1993-05-03 | 1996-07-23 | Mobil Oil Corporation | Dimercaptothiadiazole-mercaptan coupled compounds as multifunctional additives for lubricants and fuels |
| US6248701B1 (en) * | 1994-05-13 | 2001-06-19 | Henkel Corporation | Aqueous metal coating composition and process with reduced staining and corrosion |
| US5801130A (en) * | 1995-12-22 | 1998-09-01 | Exxon Research And Engineering Company | High load-carrying turbo oils containing amine phosphate and dimercaptothiadiazole derivatives |
| US5726133A (en) * | 1996-02-27 | 1998-03-10 | Exxon Research And Engineering Company | Low ash natural gas engine oil and additive system |
| US6207623B1 (en) | 2000-01-14 | 2001-03-27 | Exxonmobil Research And Engineering Company | Industrial oils of enhanced resistance to oxidation |
| WO2001051595A1 (en) * | 2000-01-14 | 2001-07-19 | Exxonmobil Research And Engineering Company | Industrial oils of enhanced resistance to oxidation |
| EP1746148A1 (en) | 2005-07-20 | 2007-01-24 | Chevron Oronite Company LLC | Crankcase lubricating oil composition for protection of silver bearings in locomotive diesel engines. |
| US8084404B2 (en) | 2005-07-20 | 2011-12-27 | Chevron Oronite Company Llc | Crankcase lubricating oil composition for protection of silver bearings in locomotive diesel engines |
| WO2010024170A1 (ja) | 2008-08-29 | 2010-03-04 | 新日本石油株式会社 | 銀含有材料と接触する潤滑油組成物 |
| US20110212863A1 (en) * | 2008-08-29 | 2011-09-01 | Kazuhiro Yagishita | Lubricating oil composition in contact with silver-containing material |
| US8802604B2 (en) | 2008-08-29 | 2014-08-12 | Jx Nippon Oil & Energy Corporation | Lubricating oil composition in contact with silver-containing material |
| US8969273B2 (en) | 2009-02-18 | 2015-03-03 | Chevron Oronite Company Llc | Lubricating oil compositions |
| US8841243B2 (en) | 2010-03-31 | 2014-09-23 | Chevron Oronite Company Llc | Natural gas engine lubricating oil compositions |
| US8796192B2 (en) | 2010-10-29 | 2014-08-05 | Chevron Oronite Company Llc | Natural gas engine lubricating oil compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1480387A (en) | 1977-07-20 |
| CA983914A (en) | 1976-02-17 |
| FR2244813B1 (cs) | 1979-09-21 |
| GB1401076A (en) | 1975-07-16 |
| FR2244813A1 (cs) | 1975-04-18 |
| US3909420A (en) | 1975-09-30 |
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