GB658182A - Improvements in or relating to lubricating compositions and the preparation of additives therefor - Google Patents
Improvements in or relating to lubricating compositions and the preparation of additives thereforInfo
- Publication number
- GB658182A GB658182A GB32434/47A GB3243447A GB658182A GB 658182 A GB658182 A GB 658182A GB 32434/47 A GB32434/47 A GB 32434/47A GB 3243447 A GB3243447 A GB 3243447A GB 658182 A GB658182 A GB 658182A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dithiophosphate
- salt
- zinc
- heterocyclic
- metal
- 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
Links
- 239000000203 mixture Substances 0.000 title abstract 8
- 230000001050 lubricating effect Effects 0.000 title abstract 5
- 239000000654 additive Substances 0.000 title 1
- -1 di-substituted dithiophosphoric acids Chemical class 0.000 abstract 18
- 229910052751 metal Inorganic materials 0.000 abstract 17
- 239000002184 metal Substances 0.000 abstract 17
- 150000003839 salts Chemical class 0.000 abstract 14
- 125000000623 heterocyclic group Chemical group 0.000 abstract 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 8
- 239000003208 petroleum Substances 0.000 abstract 8
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 6
- 229910052718 tin Inorganic materials 0.000 abstract 6
- 239000011135 tin Chemical class 0.000 abstract 6
- 229910052725 zinc Inorganic materials 0.000 abstract 6
- 239000011701 zinc Chemical class 0.000 abstract 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 5
- 229910052788 barium Inorganic materials 0.000 abstract 5
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical class [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 5
- 229910052799 carbon Inorganic materials 0.000 abstract 5
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 4
- 229910052793 cadmium Inorganic materials 0.000 abstract 4
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical class [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 abstract 4
- 229910052791 calcium Inorganic materials 0.000 abstract 4
- 239000011575 calcium Chemical class 0.000 abstract 4
- 229910052804 chromium Inorganic materials 0.000 abstract 4
- 239000011651 chromium Chemical class 0.000 abstract 4
- 229910052759 nickel Inorganic materials 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 239000001301 oxygen Substances 0.000 abstract 4
- 150000002989 phenols Chemical class 0.000 abstract 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 abstract 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 3
- CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 abstract 3
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 abstract 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical class [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 3
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 abstract 3
- 239000004411 aluminium Chemical class 0.000 abstract 3
- 229910052782 aluminium Inorganic materials 0.000 abstract 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 3
- 229910017052 cobalt Inorganic materials 0.000 abstract 3
- 239000010941 cobalt Chemical class 0.000 abstract 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical class [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 3
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 abstract 3
- 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 abstract 3
- 239000011777 magnesium Chemical class 0.000 abstract 3
- 229910052749 magnesium Inorganic materials 0.000 abstract 3
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 3
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 abstract 3
- 150000003751 zinc Chemical class 0.000 abstract 3
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 abstract 2
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 abstract 2
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 abstract 2
- DZULYTCVBHPBHV-UHFFFAOYSA-N COC(CCC(C(CCCC)CC)SP(O)(O)=S)C Chemical compound COC(CCC(C(CCCC)CC)SP(O)(O)=S)C DZULYTCVBHPBHV-UHFFFAOYSA-N 0.000 abstract 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical class [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 abstract 2
- 150000001844 chromium Chemical class 0.000 abstract 2
- 229930003836 cresol Natural products 0.000 abstract 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 abstract 2
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 abstract 2
- IFVBBMQALQEAEB-UHFFFAOYSA-N dihydroxy-[4-methyl-2-octyl-3-(oxolan-2-ylmethyl)phenyl]sulfanyl-sulfanylidene-lambda5-phosphane Chemical compound C(C1CCCO1)C=1C(=C(C=CC=1C)SP(O)(O)=S)CCCCCCCC IFVBBMQALQEAEB-UHFFFAOYSA-N 0.000 abstract 2
- 125000001033 ether group Chemical group 0.000 abstract 2
- 150000002398 hexadecan-1-ols Chemical class 0.000 abstract 2
- 229910052748 manganese Inorganic materials 0.000 abstract 2
- 239000011572 manganese Chemical class 0.000 abstract 2
- 239000010688 mineral lubricating oil Substances 0.000 abstract 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 239000003921 oil Substances 0.000 abstract 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 abstract 2
- 159000000000 sodium salts Chemical class 0.000 abstract 2
- 229910052712 strontium Inorganic materials 0.000 abstract 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical class [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 abstract 2
- 229910052716 thallium Chemical class 0.000 abstract 2
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical class [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 abstract 2
- 239000011592 zinc chloride Substances 0.000 abstract 2
- 235000005074 zinc chloride Nutrition 0.000 abstract 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 abstract 1
- MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 abstract 1
- BIZFGACNZRAGHC-UHFFFAOYSA-N C(CCCCCCCCCCC)SP(O)(O)=S.C(C)OCCO Chemical compound C(CCCCCCCCCCC)SP(O)(O)=S.C(C)OCCO BIZFGACNZRAGHC-UHFFFAOYSA-N 0.000 abstract 1
- IIKFCCTZRDUWJG-UHFFFAOYSA-N CCCCC(CC)C[S+]=P([O-])([O-])SCCC(C)OC.[Mn+2] Chemical compound CCCCC(CC)C[S+]=P([O-])([O-])SCCC(C)OC.[Mn+2] IIKFCCTZRDUWJG-UHFFFAOYSA-N 0.000 abstract 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 1
- NBAUFFYXMJTNJD-UHFFFAOYSA-L P(=S)(SC1(CCCCC1)C)(OC1(CCCCC1)C)[O-].[Ni+2].CC1(CCCCC1)SP(=S)(OC1(CCCCC1)C)[O-] Chemical compound P(=S)(SC1(CCCCC1)C)(OC1(CCCCC1)C)[O-].[Ni+2].CC1(CCCCC1)SP(=S)(OC1(CCCCC1)C)[O-] NBAUFFYXMJTNJD-UHFFFAOYSA-L 0.000 abstract 1
- 150000001661 cadmium Chemical class 0.000 abstract 1
- 159000000007 calcium salts Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- OIDPCXKPHYRNKH-UHFFFAOYSA-J chrome alum Chemical compound [K]OS(=O)(=O)O[Cr]1OS(=O)(=O)O1 OIDPCXKPHYRNKH-UHFFFAOYSA-J 0.000 abstract 1
- 150000001868 cobalt Chemical class 0.000 abstract 1
- 230000007797 corrosion Effects 0.000 abstract 1
- 238000005260 corrosion Methods 0.000 abstract 1
- 230000008021 deposition Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 239000011787 zinc oxide Substances 0.000 abstract 1
- ZWAMPTZQYZFHBO-UHFFFAOYSA-L zinc;2-ethylhexoxy-(2-ethylhexylsulfanyl)-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CCCCC(CC)COP([O-])(=S)SCC(CC)CCCC.CCCCC(CC)COP([O-])(=S)SCC(CC)CCCC ZWAMPTZQYZFHBO-UHFFFAOYSA-L 0.000 abstract 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—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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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/088—Neutral salts
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/06—Groups 3 or 13
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/08—Groups 4 or 14
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/12—Groups 6 or 16
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/14—Group 7
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/16—Groups 8, 9, or 10
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Abstract
Oil-soluble metal salts of organic di-substituted dithiophosphoric acids, derived at least in part from saturated aliphatic hydroxyethers or from heterocyclic alcohols containing only oxygen and carbon in the heterocyclic nucleus, are used as ingredients of lubricating compositions (see Group III). The metal salts may have the general formula <FORM:0658182/IV (b)/1> where n represents the valency of the metal M, R1 is a saturated aliphatic radicle containing an ether group or a heterocyclic radicle containing only oxygen and carbon in the heterocyclic nucleus, and R2 is any suitable organic nucleus. The radicle R1 may be derived from aliphatic hydroxy-ethers such as ethylene glycol monobutyl ether, diethylene glycol monoethyl ether, triethylene glycol monobutyl ether or 3-methoxy-n-butanol or from a heterocyclic alcohol such as tetrahydrofurfuryl alcohol. The radicle R2 may be derived from aliphatic alcohols such as amyl, octyl, lauryl or cetyl alcohols, alicyclic alcohols such as cyclohexanol or methyl cyclohexanol, phenols, especially alkylated phenols such as octyl cresol p-octyl phenol, p-tert. amyl phenol or tert.-butyl cresol, aromatic alcohols such as benzyl alcohol, or aliphatic hydroxy-ethers such as those already mentioned. The metal salts may be salts of barium, calcium, strontium, magnesium, zinc, aluminium, nickel, cobalt, tin, cadmium, chromium, manganese or thallium. Preparation of the metal salt of the di-substituted dithiophosphoric acid may be effected by first reacting the aliphatic hydroxyether or heterocyclic alcohol with phosphorus pentasulphide, and where a mixed organic dithiophosphate is desired an appropriate hydroxylic organic compound may be admixed with the hydroxyether or heterocyclic alcohol for simultaneous reaction with the phosphorus pentasulphide. The acid may be neutralized with caustic soda and a desired metal salt produced by the addition of a suitable salt of the metal. Alternatively the acid may be neutralized directly with the oxide or hydroxide of the desired metal. In the examples: (1) a mixture of tetrahydrofurfuryl alcohol and octyl cresol is reacted with phosphorus pentasulphide, the acid obtained is neutralized with caustic soda and the sodium salt is converted to the chromium salt of tetrahydrofurfuryl octylcresyl dithiophosphoric acid by addition of chrome alum; (2) ethylene glycol mono-n-butyl ether is reacted with phosphorus pentasulphide, the acid obtained is neutralized with caustic soda and the sodium salt is converted to the zinc salt of di - (b - butoxyethyl) - dithiophosphoric acid by addition of zinc chloride; the cadmium salt is obtained by using cadmium chloride instead of zinc chloride, and (3) a mixture of 2-ethyl-n-hexanol and 3-methoxy-n-butanol is reacted with phosphorus pentasulphide and the acid obtained is neutralized with zinc oxide to give the zinc salt of 3-methoxy-n-butyl 2-ethyl-hexyl dithiophosphoric acid. Specifications 569,939, [Group III], and 658,183 are referred to.ALSO:A lubricating composition comprises a mineral lubricating oil and a minor proportion of an oil-soluble metal salt of an organic di-substituted dithiophosphoric acid derived at least in part from a saturated aliphatic hydroxy-ether or from a heterocyclic alcohol containing only oxygen and carbon in the heterocyclic nucleus. The metal salt may have the general formula <FORM:0658182/III/1> where n represents the valency of the metal M, R1 is a saturated aliphatic radicle containing an ether group or a heterocyclic radicle containing only oxygen and carbon in the heterocyclic nucleus, and R2 is any suitable organic nucleus. The metal salt inhibits oil oxidation and bearing corrosion, substantially reduces the deposition of gum, lacquer and carbon on hot metal surfaces, and increases the film strength of the oil. The lubricating composition is particularly suitable for use as the lubricant in high-speed Diesel engines. The radicle R1 may be derived from aliphatic hydroxy-ethers such as ethylene glycol monobutyl ether, diethylene glycol monoethyl ether, triethylene glycol monobutyl ether or 3-methoxy-n-butanol or from a heterocyclic alcohol such as tetrahydrofurfuryl alcohol. The radicle R2 may be derived from aliphatic alcohols such as amyl, octyl, lauryl or cetyl alcohols, alicyclic alcohols such as cyclohexanol or methyl cyclohexanol, phenols, especially alkylated phenols such as octyl cresol, p-octyl phenol, p-tert.-amyl phenol or tert.-butyl cresol, aromatic alcohols such as benzyl alcohol, or aliphatic hydroxy ethers such as those already mentioned. Specific examples of di-substituted dithiophosphoric acids are tetrahydrofurfuryl octyl-cresyl dithiophosphoric acid, di-(b -butoxyethyl) dithiophosphoric acid, 3 - methoxy - n - butyl 2 - ethyl - hexyl dithiophosphoric acid and ethylene glycol monoethyl ether lauryl dithiophosphoric acid. The metal salts may be salts of barium, calcium, strontium, magnesium, zinc, aluminium, nickel, cobalt, tin, cadmium, chromium, manganese or thallium. Especially where a chromium salt of a di-substituted dithiophosphoric acid, the zinc salt of di-(21-butoxy-2-ethoxyethyl) dithiophosphoric acid, the calcium salt of di-(b -butoxyethyl) dithiophosphoric acid or the cobalt salt of 21-methoxy-2-ethoxyethyl methyl cyclohexyl dithiophosphoric acid is employed, the lubricating composition may also contain a metal salt of a petroleum sulphonic acid. This sulphonate may be a salt of one of the metals already listed or other polyvalent metal, but tin sulphonates are preferred. In the examples, mineral lubricating oil compositions are described containing (1) chromium tetrahydrofurfuryl octyl cresyl dithiophosphate and tin petroleum sulphonate; (2) zinc or manganese 3 - methoxy - n - butyl 2 - ethyl - n - hexyl-dithiophosphate; (3) cobalt 21-methoxy-2-ethoxyethyl methyl cyclohexyl dithiophosphate and cadmium petroleum sulphonate; (4) tin di - (b - n - butoxyethyl) dithiophosphate; (5) zinc di-b -n-butoxyethyl) dithiophosphate with or without calcium or tin petroleum sulphonate; (6) nickel or aluminium b -ethoxyethyl lauryl dithiophosphate; (7) zinc di-(3-methoxy - n - butyl) dithiophosphate and calcium petroleum sulphonate; (8) cadmium di - (b - n - butoxyethyl) dithiophosphate and barium petroleum sulphonate; (9) magnesium di - (21 - n - butoxy - 2 - ethoxyethyl) dithiophosphate and nickel petroleum sulphonate; (10) zinc di-(a -methyl-isoamyl) dithiophosphate; (11) zinc di-(2-ethyl-n-hexyl) dithiophosphate; (12) nickel di-(methyl cyclohexyl) dithiophosphate; (13) barium b -n-butoxyethyl nonyl dithiophosphate; (14) barium di-(decyl and dodecyl) dithiophosphate; (15) zinc di-(21-n-butoxy - 2 - ethoxyethyl) dithiophosphate and chromium petroleum sulphonate. Specifications 567,939 and 658,183 are referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB277989X | 1947-12-09 | ||
| GB41148X | 1948-11-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB658182A true GB658182A (en) | 1951-10-03 |
Family
ID=26238882
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32434/47A Expired GB658182A (en) | 1947-12-09 | 1947-12-09 | Improvements in or relating to lubricating compositions and the preparation of additives therefor |
| GB32502/47A Expired GB658183A (en) | 1947-12-09 | 1947-12-09 | Improvements in or relating to lubricating compositions |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32502/47A Expired GB658183A (en) | 1947-12-09 | 1947-12-09 | Improvements in or relating to lubricating compositions |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US2579038A (en) |
| CH (1) | CH277989A (en) |
| DE (1) | DE832030C (en) |
| FR (2) | FR976343A (en) |
| GB (2) | GB658182A (en) |
| NL (2) | NL69724C (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2824063A (en) * | 1956-05-11 | 1958-02-18 | Sinclair Refining Co | Lubricating oils containing a zinc dithiophosphate and nickel mahogany sulfonate |
| US2905683A (en) * | 1952-12-17 | 1959-09-22 | Lubrizol Corp | Ether containing esters of dithiophosphoric acid and salts thereof |
| US2916448A (en) * | 1957-05-31 | 1959-12-08 | Sinclair Refining Co | Oxidation inhibitor-detergent material |
| DE1090361B (en) * | 1957-01-22 | 1960-10-06 | Lubrizol Corp | Lubricant additives for internal combustion engines |
| DE1109302B (en) * | 1959-01-16 | 1961-06-22 | Lubrizol Corp | Lubricating oil |
| CN113680535A (en) * | 2021-08-24 | 2021-11-23 | 中南大学 | Alkyl ether group dithiophosphate collecting agent and preparation method and application thereof |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL76200C (en) * | 1950-05-12 | |||
| BE510012A (en) * | 1951-03-29 | |||
| US2838555A (en) * | 1951-10-12 | 1958-06-10 | Lubrizol Corp | Group ii metal salts of a mixture of simple diesters of dithiophosphoric acids |
| DE961484C (en) * | 1952-12-18 | 1957-04-04 | Exxon Research Engineering Co | Process for increasing the viscosity index of lubricating oils |
| GB801151A (en) * | 1955-01-27 | 1958-09-10 | Lubrizol Corp | Gear lubricant improving agents |
| DE1245013B (en) * | 1960-05-12 | 1967-07-20 | Sineclair Refining Company | Mineral lubricating oil |
| US3243482A (en) * | 1962-01-10 | 1966-03-29 | Gen Aniline & Film Corp | Surface-active thiophosphoric acid esters of polyglycol ethers |
| US3909447A (en) * | 1972-07-17 | 1975-09-30 | Petrolite Corp | Mixtures of thiophosphates, oxygen phosphates and pyrophosphates |
| US4042323A (en) * | 1972-07-17 | 1977-08-16 | Petrolite Corporation | Process of inhibiting corrosion of metal in an aqueous environment with mixtures of thio-, oxygen and thio- oxygen phosphates and pyrophosphates |
| US5919740A (en) * | 1998-05-29 | 1999-07-06 | Exxon Chemical Patents Inc | Alkylthiophosphate salts for lubricating oils |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2125936A (en) * | 1936-03-03 | 1938-08-09 | Sonneborn Sons Inc L | Lubricating oil |
| US2228659A (en) * | 1938-11-21 | 1941-01-14 | Standard Oil Co | Compounded mineral oil |
| US2241243A (en) * | 1939-03-25 | 1941-05-06 | Texas Co | Lubricating oil |
| USRE22829E (en) * | 1939-05-06 | 1947-01-14 | Compounded hydrocarbon oil | |
| US2322307A (en) * | 1939-06-20 | 1943-06-22 | Standard Oil Co California | Compounded oil |
| US2372244A (en) * | 1941-09-24 | 1945-03-27 | Standard Oil Co | Esters of acids of phosphorus |
| US2344392A (en) * | 1941-11-08 | 1944-03-14 | American Cyanamid Co | Crankcase lubricant and chemical compound therefor |
| US2369632A (en) * | 1941-11-13 | 1945-02-13 | American Cyanamid Co | Lubricating oils |
| US2382775A (en) * | 1942-06-16 | 1945-08-14 | American Cyanamid Co | Dithiophosphoric acids and salts thereof |
| US2344395A (en) * | 1942-06-16 | 1944-03-14 | American Cyanamid Co | Lubricating oil |
| US2383917A (en) * | 1942-07-09 | 1945-08-28 | Cities Service Oil Co | Lubricant |
| GB561941A (en) * | 1942-07-29 | 1944-06-12 | Elliott Alfred Evans | Improvements in or relating to lubricating oils |
| US2417876A (en) * | 1944-08-16 | 1947-03-25 | Tide Water Associated Oil Comp | Inhibited oil |
| US2418422A (en) * | 1944-12-11 | 1947-04-01 | Sinclair Refining Co | Lubricant |
-
0
- NL NL70344D patent/NL70344C/xx active
- NL NL69724D patent/NL69724C/xx active
-
1947
- 1947-12-09 GB GB32434/47A patent/GB658182A/en not_active Expired
- 1947-12-09 GB GB32502/47A patent/GB658183A/en not_active Expired
-
1948
- 1948-12-06 US US63844A patent/US2579038A/en not_active Expired - Lifetime
- 1948-12-06 US US63843A patent/US2579037A/en not_active Expired - Lifetime
- 1948-12-08 CH CH277989D patent/CH277989A/en unknown
- 1948-12-09 FR FR976343D patent/FR976343A/en not_active Expired
- 1948-12-09 FR FR976342D patent/FR976342A/en not_active Expired
-
1949
- 1949-01-11 DE DEP31331A patent/DE832030C/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2905683A (en) * | 1952-12-17 | 1959-09-22 | Lubrizol Corp | Ether containing esters of dithiophosphoric acid and salts thereof |
| US2824063A (en) * | 1956-05-11 | 1958-02-18 | Sinclair Refining Co | Lubricating oils containing a zinc dithiophosphate and nickel mahogany sulfonate |
| DE1090361B (en) * | 1957-01-22 | 1960-10-06 | Lubrizol Corp | Lubricant additives for internal combustion engines |
| US2916448A (en) * | 1957-05-31 | 1959-12-08 | Sinclair Refining Co | Oxidation inhibitor-detergent material |
| DE1109302B (en) * | 1959-01-16 | 1961-06-22 | Lubrizol Corp | Lubricating oil |
| CN113680535A (en) * | 2021-08-24 | 2021-11-23 | 中南大学 | Alkyl ether group dithiophosphate collecting agent and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| NL69724C (en) | |
| US2579038A (en) | 1951-12-18 |
| FR976342A (en) | 1951-03-16 |
| FR976343A (en) | 1951-03-16 |
| GB658183A (en) | 1951-10-03 |
| US2579037A (en) | 1951-12-18 |
| NL70344C (en) | |
| DE832030C (en) | 1952-02-21 |
| CH277989A (en) | 1951-09-30 |
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