US3833496A - Oil composition - Google Patents
Oil composition Download PDFInfo
- Publication number
- US3833496A US3833496A US00348625A US34862573A US3833496A US 3833496 A US3833496 A US 3833496A US 00348625 A US00348625 A US 00348625A US 34862573 A US34862573 A US 34862573A US 3833496 A US3833496 A US 3833496A
- Authority
- US
- United States
- Prior art keywords
- acid
- oil composition
- dithiocarbamate
- carbon atoms
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- -1 trimethylene radical Chemical class 0.000 claims description 52
- 239000000654 additive Substances 0.000 claims description 28
- 239000010687 lubricating oil Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 230000000996 additive effect Effects 0.000 claims description 14
- 150000003254 radicals Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 9
- 239000012990 dithiocarbamate Substances 0.000 description 8
- 229910052791 calcium Inorganic materials 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- RQPNXPWEGVCPCX-UHFFFAOYSA-N 3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O RQPNXPWEGVCPCX-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 239000004519 grease Substances 0.000 description 3
- 231100000241 scar Toxicity 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 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
- 150000001768 cations Chemical class 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229920001083 polybutene Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- ZDXGQHXSMPGQRI-UHFFFAOYSA-N 2,6-ditert-butyl-3-[(2,4-ditert-butyl-3-hydroxyphenyl)methyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC=C1CC1=CC=C(C(C)(C)C)C(O)=C1C(C)(C)C ZDXGQHXSMPGQRI-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- BBIKWYXKORRYQP-UHFFFAOYSA-N 3-sulfanyloctanoic acid Chemical compound CCCCCC(S)CC(O)=O BBIKWYXKORRYQP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BHDKXXOGPCSBQI-UHFFFAOYSA-N Methyl 3-mercaptobutanoate Chemical compound COC(=O)CC(C)S BHDKXXOGPCSBQI-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011436 cob Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 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 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- VNTXONBESJNLBI-UHFFFAOYSA-N dinonyl decanedioate Chemical compound CCCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCCC VNTXONBESJNLBI-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002171 ethylene diamines Chemical class 0.000 description 1
- BUHXFUSLEBPCEB-UHFFFAOYSA-N icosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCN BUHXFUSLEBPCEB-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- TUFJPPAQOXUHRI-KTKRTIGZSA-N n'-[(z)-octadec-9-enyl]propane-1,3-diamine Chemical compound CCCCCCCC\C=C/CCCCCCCCNCCCN TUFJPPAQOXUHRI-KTKRTIGZSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229920000196 poly(lauryl methacrylate) Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/027—Neutral salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
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- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
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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
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- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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- 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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- 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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- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
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- C10N2010/00—Metal present as such or in compounds
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- C10N2010/00—Metal present as such or in compounds
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- C10N2010/00—Metal present as such or in compounds
- C10N2010/16—Groups 8, 9, or 10
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Definitions
- a preferred embodiment of the invention is an'antiwear-antirust additive for lubricating oils and greases having the formula:
- tiwear-antirust amount of an additive said additive having the formula:
Abstract
WHEREIN R'' is selected from the group consisting of aliphatic hydrocarbon radicals containing about 8-100 carbon atoms, and hydrocarbylaminohydrocarbyl radicals having the formula:
Compounds having the formula:
Compounds having the formula:
Description
United States Patent [191 Malec [111 3,833,496 [4 Sept. 3, 1974 OIL COMPOSITION Robert E. Malec, Birmingham, Mich.
[73] Assignee: Ethyl Corporation, Richmond, Va.
[22] Filed: Apr. 6, 1973 [21] Appl. No.: 348,625
[75] Inventor:
[52] US. Cl 252/33.6, 252/47.5, 260/455 A [51] Int. Cl. C10m l/38, ClOm 1/32 [58] Field of Search 252/34, 33.6, 47.5;
[56] References Cited UNITED STATES PATENTS 7/1956 Kirshenbaum et al 252/47.5 X 7/1959 Elliott et al. 252/47.5 X
Primary ExaminerW. Cann9n Attorney, Agent, or Firm-Donald H A. Linn; Joseph D. Odenweller [57] ABSTRACT Compounds having the formula:
wherein R is selected from the group consisting of aliphatic hydrocarbon radicals containing about 8-100 carbon atoms, and hydrocarbylaminohydrocarbyl radicals having the formula:
' lected from the group consisting of hydrogen and C alkyls and R is selected from the group consisting of hydrogen, C alkyl and salt cations, are effective antiwear and antirust additives in lubricating oils and greases.
6 Claims, No Drawings OIL COMPOSITION BACKGROUND Additives are conventionally added to lubricating oil and grease to improve their properties. Antiwear additives used in the past include compounds such as zinc dialkyldithiophosphates, sulfurized sperm oil, and the like. Antirust protection can be provided by compounds such as overbased calcium sulfonates. Long chain amines such as polybutenyl ethylenediamine have been used to improve dispersancy of lubricating oils.
SUMMARY OE THE INVENTION According to the present invention, lubricating oils and greases having improved antiwear and antirust properties are provided by including in the lubricating oil composition certain 3-mercaptoalkanoic acid, [(alkylamino)alkyl] dithio-carbarnates such as 3- mercaptobutyric acid, [3(oleylamino)-propyl] dithiocarbamate.
DESCRIPTION OF THE PREFERRED EMBODIMENTS A preferred embodiment of the invention is an'antiwear-antirust additive for lubricating oils and greases having the formula:
wherein R is selected from the group consisting of aliphatic hydrocarbon radicals containing about 8-l00 carbon atoms, and hydrocarbylaminohydrocarbyl radicals having the formula:
wherein R is an aliphatic hydrocarbon radical containing about 8-l OO carbon atoms, R" is selected from the group consisting of hydrogen and C alkyls and R is a divalent aliphatic hydrocarbon radical containing about 2-10 carbon atoms, R and R are selected from the group consisting of hydrogen and alkyl radicals containing about 1-4 carbon atoms, R" is selected from the group consisting of hydrogen and C alkyls and R is selected from the group consisting of hydrogen, C alkyl and salt cations. Useful salt cations include the cations of the alkaline earth metals such as calcium, magnesium, strontium, and barium; ammonium ions formed from ammonia; alkyl and alkenyl amines such as methylamine, dimethylamine, trimethylamine, triethylamine, tributylamine, ethanolamine,
, diethanolamine, triethanolamine, morpholine, stearylamine, oleylamine, palmylamine, laurylamine, eicosylamine, eicosenylamine, and the like; and other metal cations such as zinc, aluminum, nickel, manganese, iron, and the like.
Representative examples of theabove additives include:
B-mercaptopropionic acid, n-octyldithiocarbamate 3-mercaptobutyric acid, stearyldithiocarbamate calcium 3-mercaptobutyrate, oleyldithiocarbamate zinc 3-rnercaptopropionate, palmyldithiocarbamate trimethylammonium 3-mercaptohexanoate, C
polybutenyl dithiocarbamate manganese B-mercaptobutyrate, stearyldithiocarbamate barium B-mercaptOheptanOate, eicosyldithiocarbamate magnesium 3-mercaptobutyrate, eicosenyldithiocarbamate methyl 3-mercaptobutyrate, stearyldithiocarbamate decyl 3-mercaptohexanoate, octyldithiocarbamate triethanolammonium 3-mercaptobutyrate, oleyldithio-carbamate A most preferred embodiment of this invention is an antiwear-antirust additive for lubricating oils and greases, said additive having the formula:
wherein R is an aliphatic hydrocarbon radical containing from about 8-100 carbon atoms, R is a divalent aliphatic hydrocarbon radical containing from 2 to about 10 carbon atoms, and R and R are selected from the group consisting of hydrogen and alkyl radicals containing one to about four carbon atoms. Since the compounds contain both a basic amine functional group and a carboxylic acid they can exist in the form of a zwitterion and are shown in that form in Formula II. Representative'examples of such additives include: 3-mercaptopropionic acid, [2( 9- eicosenylamino)ethyl] dithiocarbamate 3-mercapto-2-methylbutyric acid, [6(octylamino)- hexyl] dithiocarbamate 3-mercaptoheptanoic acid, [l0(laurylamino)decyl] dithiocarbamate 3-merCapto-Z-methylhexanoic acid, [4( lhexylbutylamino) butyl] dithiocarbamate -3 -mercapto-2-butylheptanoic acid, [3( pentacontenylamino) propyl] dithiocarbamate 3-mercaptobutyric acid, [2(hexacontylamino)ethyl] dithiocarbamate 3-mercaptopropionic acid, [3(octacontylamino)propyl] dithiocarbamate 3-mercaptohexanoic acid, [3(C polybutenylamino) propyl] dithiocarbamate 3-mercaptobutyric acid, [3(C -polypropenylamino) propyl] dithiocarbamate 3-mercaptooctanoic acid, [3(dodecenylamino)butyl] dithiocarbamate 3-mercaptopropionic acid, [3(tetracosylamino)propyl] dithiocarbamate 3-mercaptobutyric acid, [6(stearylamino)hexyl] dithiocarbamate B-mercaptopentanoic acid, [4(palmylamino)butyl] dithiocarbamate S-mercaptobutyric acid,
nonacontenylamino)propyl] dithiocarbamate A preferred class of additives are those of Formula ll wherein R contains about 8-22 carbon atoms, R: is the trimethylene radical (Cl-I9 R, is the methyl radical, and R is hydrogen. Examples of these compounds are:
3-mercaptobutyric acid, [3(oleylamino)propyl] dithiocarbamate 3-mercaptobutyric acid, [3(stearylamino)propyl] dithiocarbamate 3-mercaptobutyric acid, [3(palmylamino)propyl] dithiocarbamate The additives are readily prepared by reacting an aliphatic hydrocarbylaminohydrocarbylamine with carbon disulfide to form the corresponding hydrocarbylaminohydrocarbyl dithio-carbamic acid and reacting this with an appropriate alpha-unsaturated aliphatic carboxylic acidsuch as acrylic acid, crotonic acid, a-methyl crotonic acid, a, B-diethyl acrylic acid,
fi-butyl acrylic acid, a-butyl acrylic acid, and the like The following example illustrates the manner in which the additives can be prepared.)
EXAMPLE 1 To a solution of 175 grams of N-oleyl-1,3- propanediamine and 175 grams of isopropyl alcohol was added a solution of 40 grams of carbon disulfide and 40 grams of isopropyl alcohol over a 1 hour period at 0l0 C. The unreacted carbon disulfide was distilled off and 50 grams each of crotonic acid, isopropyl alcohol and methanol was added. The mixture was stirred at 0l0 C. for 2 hours and then allowed to warm to room temperature. The product was diluted with hexane and washed with water, following which volatile material was distilled out under vacuum to.
yield 184 grams of a low melting solid.
EXAMPLE 2 A portion of the-product from Example l was diluted with hexane, filtered, water washed, and then the hexane distilled out. The resultant product was diluted with neutral mineral oil to obtain a 67 weight per cent active concentrate. This was diluted with hexane and washed with aqueous ammonia. Powdered solid carbon dioxide was added and stirred into the mixture; The mixture was then water washed, following which hexane was distilled out, leaving a viscous yellow liquid concentrate.
Modification of the above procedure by substitution of different starting hydrocarbylaminohydrocarbylamines and different alpha-unsaturated aliphatic carboxylic acids will lead to the other additives within the scope of this invention.
The additives are useful in lubricating oils and greases-including both mineral and synthetic. Synthetic oils include polyolefin oils (e.g., polybutene oil, decene oligomer, and the like), synthetic esters (e.g., dinonyl sebacate, trioctanoic acid ester of trimethylolpropane, and the like), polyglycol oils, and the like. Greases are made from these oils by adding a thickening agent such as sodium, calcium, lithium, or aluminum salts of fatty methylenebis(2,6-di-tert-butylphenol),
acids such as stearic acid. The oils and greases are prepared by blending an antiwear and antirust amount of the additive into the oil or grease. A useful concentration is from about 0.1 to 5 weight per cent. The additives may be added in the form of a concentrate such as the mineral oil diluted concentrate described in Example 2.
Other additives may be included in the oil or grease compositions. These include such additives as zinc dialkyl-dithiophosphates, barium phenates, calcium phenates, calcium aryl sulfonates, magnesium aryl sulfonates, overbased calcium aryl sulfonates, barium polybutenyl phosphonates; antioxidants such as 4,4- a-dimethylamino-2,6-di-tert-butyl-p-cresol; dispersants such as polybutenyl succinimides of ethylenepolyamines, polybutenyl ethylenediamines, viscosity index improvers such as polybutenes, ethylene-propylene copolymers, polylauryl methacrylates, and the like.
Tests have been carried out to demonstrate the antiwear and antirust properties of the additives. The first is known as the -four -ball cam and tappet test. In this test, three steel balls are placed in a triangular manner in a circular retainer containing the test oil. A fourth ball is placed on top of these three to form a triangular pyramid. A 50 Kg load is placed on the top ball and it is rotated at 1,800 r.p.m. for one hour with the oil heated to C. This test has previously been shown to correlate well with the cam and tappet wear of an internal combustion engine. Criteria is the average scar diameter formed on the three bottom balls. A scar diameter of 1 mm or less is considered satisfactory.
The test was carried out on a non-additive neutral oil and on triplicate samples containing 1 weight per cent of the additive of Example 1 3-mercaptobutyric acid, [3(oleylamino)-propyl] dithiocarbamate. The re sults obtained were as follows.
TABLE 1 Additive Average scar diameter (mm) None I v 2.3 Example l (l%) 0.92, 0.99, 0.89
' concentrate of Example 2. The results were as follows.
TABLE 2 Additive Results None both fail Example 2 (1%) all pass These results demonstrate the excellent antiwear and 5 antirust properties of the present additives.
tiwear-antirust amount of an additive, said additive having the formula:
wherein R is selected from the group consisting of aliphatic hydrocarbon radicals containing about 8-100 carbon atoms, and hydrocarbylaminohydrocarbyl radicals having the formula:
R1 NRIII! wherein R is an aliphatic hydrocarbon radical containing about 8-100 carbon atoms, R" is selected from the group consisting of hydrogen and C alkyls and R is a divalent aliphatic hydrocarbon radical containing about 2-10 carbon atoms, R; and R are selected from the group consisting of hydrogen and alkyl radicals containing about 1-4 carbon atoms, R" is selected from the group consisting of hydrogen and C alkyl and R' is selected from the group consisting of hydrogen and salt cations, said salt cations selected from the group consisting of alkaline earth metals, ammonium, alkyl amine, alkenyl amine, alkanol amine, zinc, aluminum, nickel, manganese and iron.
2. A lubricating oil composition as defined in claim 1 containing an antiwear-antirust additive wherein said additive has the formula:
wherein R is an aliphatic hydrocarbon radical containing from about 8-100 carbon atoms, R is a divalent aliphatic hydrocarbon radical containing from two to about 10 carbon atoms, and R and R are selected from the group consisting of hydrogen and alkyl radicals containing one to about four carbon atoms.
3. A lubricating oil composition of claim 2 wherein R contains about 8-22 carbon atoms, R is the trimethylene radical, R is the methyl radical, and R is hydrogen.
4. A lubricating oil composition of claim 3 wherein R is the oleyl radical.
5. A lubricating oil composition of claim 3 wherein R is the stearyl radical.
6. A lubricating oil composition of claim 3 wherein R is the palmyl radical.
Claims (5)
- 2. A lubricating oil composition as defined in claim 1 containing an antiwear-antirust additive wherein said additive has the formula:
- 3. A lubricating oil composition of claim 2 wherein R1 contains about 8-22 carbon atoms, R2 is the trimethylene radical, R3 is the methyl radical, and R4 is hydrogen.
- 4. A lubricating oil composition of claim 3 wherein R1 is the oleyl radical.
- 5. A lubricating oil composition of claim 3 wherein R1 is the stearyl radical.
- 6. A lubricating oil composition of claim 3 wherein R1 is the palmyl radical.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US00348625A US3833496A (en) | 1973-04-06 | 1973-04-06 | Oil composition |
US473129A US3890363A (en) | 1973-04-06 | 1974-05-24 | Oil additive |
Applications Claiming Priority (2)
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US00348625A US3833496A (en) | 1973-04-06 | 1973-04-06 | Oil composition |
US473129A US3890363A (en) | 1973-04-06 | 1974-05-24 | Oil additive |
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US00348625A Expired - Lifetime US3833496A (en) | 1973-04-06 | 1973-04-06 | Oil composition |
US473129A Expired - Lifetime US3890363A (en) | 1973-04-06 | 1974-05-24 | Oil additive |
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US473129A Expired - Lifetime US3890363A (en) | 1973-04-06 | 1974-05-24 | Oil additive |
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Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4076639A (en) * | 1976-08-30 | 1978-02-28 | Mobil Oil Corporation | Lubricant compositions |
US4758362A (en) * | 1986-03-18 | 1988-07-19 | The Lubrizol Corporation | Carbamate additives for low phosphorus or phosphorus free lubricating compositions |
US4863622A (en) * | 1988-03-31 | 1989-09-05 | Pennzoil Products Company | Phosphorus-free antiwear/antifriction additives |
US4885365A (en) * | 1988-05-20 | 1989-12-05 | Ethyl Petroleum Additives, Inc. | Dithiocarbanate lubricant compositions |
US4957643A (en) * | 1988-05-20 | 1990-09-18 | Ethyl Petroleum Additives, Inc. | Lubricant compositions |
US4997969A (en) * | 1988-12-12 | 1991-03-05 | The Lubrizol Corporation | Carbamate additives for lubricating compositions |
US5180510A (en) * | 1988-03-31 | 1993-01-19 | Ethyl Petroleum Additives, Inc. | Antioxidant additive and lubricating oil containing same |
US5370806A (en) * | 1989-12-21 | 1994-12-06 | Mobil Oil Corporation | Borated dihydrocarbyl dithiocarbamate lubricant additives and composition thereof |
US5674820A (en) * | 1995-09-19 | 1997-10-07 | The Lubrizol Corporation | Additive compositions for lubricants and functional fluids |
US5693598A (en) * | 1995-09-19 | 1997-12-02 | The Lubrizol Corporation | Low-viscosity lubricating oil and functional fluid compositions |
US5705458A (en) * | 1995-09-19 | 1998-01-06 | The Lubrizol Corporation | Additive compositions for lubricants and functional fluids |
US5726132A (en) * | 1997-02-28 | 1998-03-10 | The Lubrizol Corporation | Oil composition for improving fuel economy in internal combustion engines |
US5759965A (en) * | 1995-10-18 | 1998-06-02 | The Lubrizol Corporation | Antiwear enhancing composition for lubricants and functional fluids |
WO1998030660A1 (en) * | 1997-01-10 | 1998-07-16 | Uniroyal Chemical Company, Inc. | Dithiocarbamyl carboxylic acids and their use as multifunctional additives for lubricating oils |
US5902776A (en) * | 1995-09-19 | 1999-05-11 | The Lubrizol Corporation | Additive compositions for lubricants and functional fluids |
US6001782A (en) * | 1998-12-17 | 1999-12-14 | The Lubrizol Corporation | Metal overbased fatty amines further derivatized to contain covalently bound sulfer and/or phorphorus useful as antiwear/extreme pressure additives |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4360438A (en) * | 1980-06-06 | 1982-11-23 | R. T. Vanderbilt Company, Inc. | Organomolybdenum based additives and lubricating compositions containing same |
JPS6084394A (en) * | 1983-09-19 | 1985-05-13 | Idemitsu Kosan Co Ltd | Fatigue life extending lubricant |
US4859352A (en) * | 1988-02-29 | 1989-08-22 | Amoco Corporation | Low temperature high performance grease |
JP2794678B2 (en) * | 1991-08-26 | 1998-09-10 | 株式会社 半導体エネルギー研究所 | Insulated gate semiconductor device and method of manufacturing the same |
JPH08209171A (en) * | 1994-11-15 | 1996-08-13 | Lubrizol Corp:The | Lubricant and fluid containing thiocarbamate and phosphorus-containing ester |
DE102008003828B3 (en) * | 2008-01-10 | 2009-09-03 | Clariant International Limited | Use of salts as corrosion inhibitors with increased biodegradability and reduced toxicity and these salts |
DE102008003826B4 (en) * | 2008-01-10 | 2010-07-22 | Clariant International Limited | Use of salts as corrosion inhibitors with increased biodegradability and reduced toxicity and these salts |
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US2756249A (en) * | 1952-11-24 | 1956-07-24 | Exxon Research Engineering Co | Phenoxyalkyl dithiocarbamates |
US2897152A (en) * | 1956-03-08 | 1959-07-28 | Wakefield & Co Ltd C C | Lubricating oils |
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US2841530A (en) * | 1955-05-18 | 1958-07-01 | Ameringen Haebler Inc Van | Hair waving compositions containing secondary amino aliphatic alcohol dithiocarbamates |
US3180791A (en) * | 1960-12-28 | 1965-04-27 | Montedison Spa | Method of controlling fungi with organic sulfur ester compounds |
-
1973
- 1973-04-06 US US00348625A patent/US3833496A/en not_active Expired - Lifetime
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1974
- 1974-05-24 US US473129A patent/US3890363A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US2756249A (en) * | 1952-11-24 | 1956-07-24 | Exxon Research Engineering Co | Phenoxyalkyl dithiocarbamates |
US2897152A (en) * | 1956-03-08 | 1959-07-28 | Wakefield & Co Ltd C C | Lubricating oils |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4076639A (en) * | 1976-08-30 | 1978-02-28 | Mobil Oil Corporation | Lubricant compositions |
US4758362A (en) * | 1986-03-18 | 1988-07-19 | The Lubrizol Corporation | Carbamate additives for low phosphorus or phosphorus free lubricating compositions |
US4863622A (en) * | 1988-03-31 | 1989-09-05 | Pennzoil Products Company | Phosphorus-free antiwear/antifriction additives |
US5180510A (en) * | 1988-03-31 | 1993-01-19 | Ethyl Petroleum Additives, Inc. | Antioxidant additive and lubricating oil containing same |
US4885365A (en) * | 1988-05-20 | 1989-12-05 | Ethyl Petroleum Additives, Inc. | Dithiocarbanate lubricant compositions |
US4957643A (en) * | 1988-05-20 | 1990-09-18 | Ethyl Petroleum Additives, Inc. | Lubricant compositions |
US4997969A (en) * | 1988-12-12 | 1991-03-05 | The Lubrizol Corporation | Carbamate additives for lubricating compositions |
US5370806A (en) * | 1989-12-21 | 1994-12-06 | Mobil Oil Corporation | Borated dihydrocarbyl dithiocarbamate lubricant additives and composition thereof |
US5674820A (en) * | 1995-09-19 | 1997-10-07 | The Lubrizol Corporation | Additive compositions for lubricants and functional fluids |
US5693598A (en) * | 1995-09-19 | 1997-12-02 | The Lubrizol Corporation | Low-viscosity lubricating oil and functional fluid compositions |
US5705458A (en) * | 1995-09-19 | 1998-01-06 | The Lubrizol Corporation | Additive compositions for lubricants and functional fluids |
US5902776A (en) * | 1995-09-19 | 1999-05-11 | The Lubrizol Corporation | Additive compositions for lubricants and functional fluids |
US5759965A (en) * | 1995-10-18 | 1998-06-02 | The Lubrizol Corporation | Antiwear enhancing composition for lubricants and functional fluids |
WO1998030660A1 (en) * | 1997-01-10 | 1998-07-16 | Uniroyal Chemical Company, Inc. | Dithiocarbamyl carboxylic acids and their use as multifunctional additives for lubricating oils |
US5726132A (en) * | 1997-02-28 | 1998-03-10 | The Lubrizol Corporation | Oil composition for improving fuel economy in internal combustion engines |
US6001782A (en) * | 1998-12-17 | 1999-12-14 | The Lubrizol Corporation | Metal overbased fatty amines further derivatized to contain covalently bound sulfer and/or phorphorus useful as antiwear/extreme pressure additives |
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