GB916505A - Amine salts and lubricating compositions containing the same - Google Patents
Amine salts and lubricating compositions containing the sameInfo
- Publication number
- GB916505A GB916505A GB26159/59A GB2615959A GB916505A GB 916505 A GB916505 A GB 916505A GB 26159/59 A GB26159/59 A GB 26159/59A GB 2615959 A GB2615959 A GB 2615959A GB 916505 A GB916505 A GB 916505A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- carbon atoms
- phosphorus
- aliphatic
- oleylamine
- 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
- -1 Amine salts Chemical class 0.000 title abstract 8
- 239000000203 mixture Substances 0.000 title abstract 4
- 230000001050 lubricating effect Effects 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- 239000005864 Sulphur Chemical group 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 239000010687 lubricating oil Substances 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 235000007586 terpenes Nutrition 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 2
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 abstract 2
- FECYWCXKWXPHPP-UHFFFAOYSA-N [Ca][Zn][Ba] Chemical group [Ca][Zn][Ba] FECYWCXKWXPHPP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 2
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 abstract 2
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 abstract 2
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 abstract 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000004615 ingredient Substances 0.000 abstract 2
- 239000011777 magnesium Chemical group 0.000 abstract 2
- 229910052749 magnesium Chemical group 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 2
- 150000003582 thiophosphoric acids Chemical class 0.000 abstract 2
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 229930006739 camphene Natural products 0.000 abstract 1
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- SZXCCXFNQHQRGF-UHFFFAOYSA-N di(propan-2-yloxy)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)OP(S)(=S)OC(C)C SZXCCXFNQHQRGF-UHFFFAOYSA-N 0.000 abstract 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 abstract 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 150000003016 phosphoric acids Chemical class 0.000 abstract 1
- ZMWBGRXFDPJFGC-UHFFFAOYSA-M potassium;propan-2-yloxymethanedithioate Chemical compound [K+].CC(C)OC([S-])=S ZMWBGRXFDPJFGC-UHFFFAOYSA-M 0.000 abstract 1
- CXYRUNPLKGGUJF-RAFJPFSSSA-M scopolamine methobromide Chemical compound [Br-].C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)C)=CC=CC=C1 CXYRUNPLKGGUJF-RAFJPFSSSA-M 0.000 abstract 1
- 150000003505 terpenes Chemical class 0.000 abstract 1
- 239000012991 xanthate Substances 0.000 abstract 1
- 150000003751 zinc Chemical class 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
- C10M137/105—Thio derivatives not containing metal
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/17—Esters of thiophosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
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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
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
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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
- 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
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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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
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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
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
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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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
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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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/08—Halogenated waxes
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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
- 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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- 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
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
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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
- 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
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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
- 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
- C10M2223/043—Ammonium or amine salts thereof
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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
- 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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- 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
- C10M2223/047—Thioderivatives not containing metallic elements
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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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- 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
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Lubricants (AREA)
Abstract
Lubricating oil compositions comprise a major proportion of a hydrocarbon lubricating oil and a minor proportion of an amine salt of general formula <FORM:0916505/III/1> in which m and n are from 0-17, m+n being from 9 to 17, R1 is a dimethylene, vinylene, or sulphurized vinylene group, each of the R2 and R3 is a hydrogen atom or an aliphatic group with 1 to 4 carbon atoms, X is oxygen or sulphur and each of R4 and R5 is an aliphatic or cycloaliphatic group with 1 to 12 carbon atoms (see Group IV(b)) for example oleylamine p and stearylamine o,o-di(1,3-dimethyl butyl) phosphorodithioates and oleylamine o,o-di-isopropylphosphorodithioate. Additional ingredients comprising a chlorinated aliphatic hydrocarbon in which a part only of the chlorine has been replaced by a thiocarbonate group, e.g. a chlorinated naphtha reacted with potassium isopropyl xanthate to give a product with 11% sulphur, 16% xanthate and 34% of chlorine; a metal salt of a dithio acid of phosphorus of general formula <FORM:0916505/III/2> where M is zinc barium calcium or magnesium and X is 1 (phosphoric acids) or O (phosphinic acids); and a phosphorized and sulphurized dicyclic terpene obtained by reacting cacene, pinene, camphene and fenchene with a phosphorus sulphide, e.g. phosphorus penta sulphide are used singly or in admixture.ALSO:The invention comprises amine salts of general formula <FORM:0916505/IV (b)/1> in which m and n are integers from 0 to 17, m + n being from 9 to 17, R1 is a dimethylene, vinylene, or sulphurised vinylene group, each of the R2 and R3 is a hydrogen atom or an aliphatic group of 1 to 4 carbon atoms, X is oxygen or sulphur, and each of R4 to R5 is an aliphatic or cycloaliphatic group containing one to twelve carbon atoms, the minimum number of carbon atoms in the two groups being 3 provided that when m + n is 9, each of R4 and R5 may not contain more than 9 carbon atoms. The salts are prepared by the reaction of amines of general formula <FORM:0916505/IV (b)/2> with one or more thiophosphoric acids of formula, <FORM:0916505/IV (b)/3> Lists of amines and thiophosphoric acids are given and examples describe the preparation of oleylamine and stearylamine O,O-di(1,3-dimethylbutyl)phosphorodithioate, and oleylamine O,O - diisopropylphosphorodithioate which are claimed. The compounds are used in lubricating compositions with hydrocarbon lubricating oils with or without additional ingredients (see Group III). Chlorinated aliphatic hydrocarbons in which part of the chlorine has been replaced by a thiocarbonate group; metal salts such as zinc barium calcium and magnesium of a dithio acid of phosphorus e.g. a zinc salt of O,O-di(1,32-dimethylbutyl) dithiophosphoric acid; and a phosphorised and sulphurised dicyclic terpene obtained by reacting phosphorus sulphide with the terpene, e.g. phosphorus pentasulphide reacted with pinene may be used as the additional additives in the compositions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US751902A US3002014A (en) | 1958-07-30 | 1958-07-30 | S-amine phosphorothioates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB916505A true GB916505A (en) | 1963-01-23 |
Family
ID=25024001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26159/59A Expired GB916505A (en) | 1958-07-30 | 1959-07-30 | Amine salts and lubricating compositions containing the same |
Country Status (2)
| Country | Link |
|---|---|
| US (2) | US3002014A (en) |
| GB (1) | GB916505A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2300769A1 (en) * | 1975-02-17 | 1976-09-10 | Basf Ag | PROCESS FOR THE PREPARATION OF SALTS OF O, S-DITHIOPHOSPHORIC ACIDS |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3397145A (en) * | 1958-12-29 | 1968-08-13 | Universal Oil Prod Co | Hydrocarbon oils containing alkylthiophosphoric acid salts of polymeric condensation products |
| US3197405A (en) * | 1962-07-09 | 1965-07-27 | Lubrizol Corp | Phosphorus-and nitrogen-containing compositions and process for preparing the same |
| NL297665A (en) * | 1962-09-07 | |||
| US3238132A (en) * | 1962-11-29 | 1966-03-01 | Universal Oil Prod Co | Stabilization of organic substances with dithiophosphate salts |
| US3201447A (en) * | 1962-11-29 | 1965-08-17 | Universal Oil Prod Co | Ether amine salts of dithiophosphoric acid mono and diesters |
| US3359347A (en) * | 1963-12-12 | 1967-12-19 | Universal Oil Prod Co | Addition reaction products of oxyalkylenated phosphorus compounds and nu-containing polymers |
| US3340329A (en) * | 1963-12-12 | 1967-09-05 | Universal Oil Prod Co | Amine salts of oxyalkylenated hydroxyhydrocarbon thiophosphates |
| US3476833A (en) * | 1966-05-02 | 1969-11-04 | Exxon Research Engineering Co | S - (2 - aminoethyl)dithiophosphates and process for the preparation thereof |
| US3533943A (en) * | 1966-11-10 | 1970-10-13 | Mobil Oil Corp | Lubricant compositions |
| US3519563A (en) * | 1967-10-31 | 1970-07-07 | Chevron Res | Thiophosphate salts of aralkylene diamines as antiwear,extreme pressure and oxidation inhibitor agents |
| GB1357745A (en) * | 1971-05-05 | 1974-06-26 | Exxon Research Engineering Co | Lubricating oil compositions |
| US4036746A (en) * | 1974-08-16 | 1977-07-19 | Minerec Corporation | Flotation with amine-stabilized dialkyl dithiophosphates |
| US3971836A (en) * | 1974-08-16 | 1976-07-27 | Minerec Corporation | Amine-stabilized dialkyl dithiophosphates |
| US4101427A (en) * | 1977-02-09 | 1978-07-18 | Exxon Research & Engineering Co. | Lubricant composition |
| FR2427381A1 (en) * | 1978-05-29 | 1979-12-28 | Exxon Research Engineering Co | Lubricants with improved antifriction properties - contg. amine and metal salts of di:alkyl di:thiophosphate cpds. |
| IT1137938B (en) * | 1981-06-26 | 1986-09-10 | Anic Spa | MULTIFUNCTIONAL ADDITIVES FOR LUBRICANTS |
| US4721802A (en) * | 1983-01-07 | 1988-01-26 | The Lubrizol Corporation | Dithiophosphorus/amine salts |
| US4774351A (en) * | 1983-01-07 | 1988-09-27 | The Lubrizol Corporation | Aqueous fluids compositions containing dithiophosphorus/amine salts |
| JPH0826340B2 (en) * | 1984-02-14 | 1996-03-13 | ザ▲ルーブリゾル コーポレイション | Compositions containing nitrogen and phosphorus, and aqueous systems containing the compositions |
| US5246604A (en) * | 1984-10-29 | 1993-09-21 | Chevron Research Company | Grease composition with improved extreme pressure and antiwear properties |
| US4755311A (en) | 1986-08-14 | 1988-07-05 | The Lubrizol Corporation | Phosphorus-, sulfur- and boron-containing compositions, and lubricant and functional fluid compositions containing same |
| JPH07197068A (en) * | 1993-12-30 | 1995-08-01 | Tonen Corp | Lubricating oil composition |
| US5545237A (en) * | 1994-07-08 | 1996-08-13 | Exxon Research And Engineering Company | Smoke reducing additive for two-cycle engine fuel mixture |
| DE69931758T2 (en) | 1998-07-06 | 2007-06-06 | The Lubrizol Corp., Wickliffe | MIXED PHOSPHORUS COMPOUNDS AND LUBRICANTS CONTAINING THEREOF |
| US7759294B2 (en) * | 2003-10-24 | 2010-07-20 | Afton Chemical Corporation | Lubricant compositions |
| EP1819739B1 (en) | 2004-12-09 | 2019-07-24 | The Lubrizol Corporation | Process of preparation of an additive |
| US20090093384A1 (en) * | 2007-10-03 | 2009-04-09 | The Lubrizol Corporation | Lubricants That Decrease Micropitting for Industrial Gears |
| IN2014CN02934A (en) | 2011-10-18 | 2015-07-03 | Cytec Tech Corp | |
| AP2014007573A0 (en) | 2011-10-18 | 2014-04-30 | Cytec Tech Corp | Froth flotation processes |
| PE20190734A1 (en) | 2011-10-18 | 2019-05-23 | Cytec Tech Corp | COLLECTOR COMPOSITIONS AND METHODS OF USE OF THE SAME |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2382775A (en) * | 1942-06-16 | 1945-08-14 | American Cyanamid Co | Dithiophosphoric acids and salts thereof |
| US2389718A (en) * | 1943-01-07 | 1945-11-27 | American Cyanamid Co | Disubstituted dithiophosphates |
| US2447288A (en) * | 1946-03-06 | 1948-08-17 | Gulf Oil Corp | Primary aliphatic amine salts of dialiphatic substituted mono-thiophosphoric acids |
| US2647140A (en) * | 1949-04-16 | 1953-07-28 | Bayer Ag | Process for the production of dialkylthiophosphates |
| US2586656A (en) * | 1949-08-18 | 1952-02-19 | American Cyanamid Co | S-aminoalkylidene dithiophosphoric acid triesters |
| US2766207A (en) * | 1952-12-31 | 1956-10-09 | Exxon Research Engineering Co | Hydrocarbon oil products |
| US2809934A (en) * | 1953-10-01 | 1957-10-15 | Standard Oil Co | Detergent lubricants and lubricating oil additives and process of making the same |
| US2850452A (en) * | 1954-06-28 | 1958-09-02 | Monsanto Chemicals | Lubricant |
| US2798045A (en) * | 1954-09-27 | 1957-07-02 | Shell Dev | Lubricating compositions |
| US2863904A (en) * | 1955-05-09 | 1958-12-09 | Gulf Oil Corp | Amine salts of di oxo-octyl orthophosphates |
| US2894951A (en) * | 1957-04-25 | 1959-07-14 | Pure Oil Co | Heterocyclic polyamine salts of phosphorodithioic acid esters and compositions containing the same |
| US2903393A (en) * | 1958-01-17 | 1959-09-08 | Virginia Carolina Chem Corp | Diethylamine addition products of acid phosphates |
-
0
- US US3103492D patent/US3103492A/en not_active Expired - Lifetime
-
1958
- 1958-07-30 US US751902A patent/US3002014A/en not_active Expired - Lifetime
-
1959
- 1959-07-30 GB GB26159/59A patent/GB916505A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2300769A1 (en) * | 1975-02-17 | 1976-09-10 | Basf Ag | PROCESS FOR THE PREPARATION OF SALTS OF O, S-DITHIOPHOSPHORIC ACIDS |
Also Published As
| Publication number | Publication date |
|---|---|
| US3002014A (en) | 1961-09-26 |
| US3103492A (en) | 1963-09-10 |
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