EP0168110A1 - Verfahren zur Herstellung von geschwefelten, überbasischen Salicylaten - Google Patents
Verfahren zur Herstellung von geschwefelten, überbasischen Salicylaten Download PDFInfo
- Publication number
- EP0168110A1 EP0168110A1 EP85201082A EP85201082A EP0168110A1 EP 0168110 A1 EP0168110 A1 EP 0168110A1 EP 85201082 A EP85201082 A EP 85201082A EP 85201082 A EP85201082 A EP 85201082A EP 0168110 A1 EP0168110 A1 EP 0168110A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- product
- metal
- aliphatic hydrocarbon
- salicylic acid
- meq
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- 150000003873 salicylate salts Chemical class 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 229910052751 metal Inorganic materials 0.000 claims abstract description 21
- 239000002184 metal Substances 0.000 claims abstract description 21
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims abstract description 21
- -1 sulphur halide Chemical class 0.000 claims abstract description 14
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 12
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 12
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229960004889 salicylic acid Drugs 0.000 claims abstract description 11
- 239000005864 Sulphur Substances 0.000 claims abstract description 10
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims abstract description 6
- 229960001860 salicylate Drugs 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 230000001131 transforming effect Effects 0.000 claims abstract description 3
- 239000000047 product Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 16
- 239000003921 oil Substances 0.000 claims description 14
- 239000012141 concentrate Substances 0.000 claims description 6
- 239000010687 lubricating oil Substances 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 150000001639 boron compounds Chemical class 0.000 claims description 2
- 239000000446 fuel Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 239000010688 mineral lubricating oil Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 4
- 239000000920 calcium hydroxide Substances 0.000 description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 238000006114 decarboxylation reaction Methods 0.000 description 4
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 229920002367 Polyisobutene Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 2
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical class ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- XOJRBTBFGUKLPU-UHFFFAOYSA-N 2,5-ditert-butyl-4-[(2,5-ditert-butyl-4-hydroxyphenyl)methyl]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(CC=2C(=CC(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1C(C)(C)C XOJRBTBFGUKLPU-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 229910018105 SCl2 Inorganic materials 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000003819 basic metal compounds Chemical class 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229940059904 light mineral oil Drugs 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
- C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals
Definitions
- This invention relates to a process for the preparation of sulphurized overbased metal aliphatic hydrocarbon-substituted salicylates by sulphurization of an aliphatic hydrocarbon-substituted salicylic acid or a metal salt thereof, to products thus prepared and to oil compositions containing them.
- This invention therefore relates to a process for the preparation of sulphurized overbased, metal aliphatic hydrocarbon-substituted salicylates by sulphurization of an aliphatic hydrocarbon-substituted salicylic acid or a metal salt thereof with a sulphur halide, and subsequently by transforming the reaction product into an overbased metal salicylate.
- the invention furthermore relates to the products thus prepared and to oil compositions containing them.
- Suitable metals of the overbased metal salicylates are e.g. alkali metals, such as Li, Cs, Na and K, alkaline earth metals, such as Ca, Ba, Sr and Mg, and polyvalent metals, such as Zn and Cr.
- Suitable aliphatic hydrocarbon-substituted salicylic acids are described in the above-mentioned British patent specifications. Preferred are C 8-30 alkyl salicylic acids.
- an alkali metal salt in particular the sodium salt, is preferred.
- the sulphurization with sulphur halide is preferably carried out in a solvent such as aliphatic hydrocarbons, e.g. n-hexane.
- a solvent such as aliphatic hydrocarbons, e.g. n-hexane.
- aromatic solvents such as xylene
- Preferred sulphur halides are sulphur chlorides, such as SCl 2 and S 2 C1 2 .
- the reaction can be carried out at ambient temperature, although some heating may be applied, e.g. up to 60 °C.
- the molar ratio of S: substituted salicylic acid or salicylate is e.g. 0.25 to 3 preferably 0.5 to 2.
- reaction mixture may then be acidified, if necessary, to obtain the free sulphurized acid and filtered if desirable.
- the product is used for the preparation of the corresponding overbased salicylates which combine good detergency with reduced wear in lubricating oil compositions.
- the overbasing step can be carried out by reacting the resulting product in a solvent, such as a hydrocarbon solvent, preferably an aromatic hydrocarbon solvent, such as xylene, with a basic metal compound, preferably a hydroxide, and carbon dioxide, as described in e.g. British patent specification 786167.
- a solvent such as a hydrocarbon solvent, preferably an aromatic hydrocarbon solvent, such as xylene
- a basic metal compound preferably a hydroxide, and carbon dioxide, as described in e.g. British patent specification 786167.
- the degree of overbasing is expressed as the basicity index (B.I.), defined as the equivalent ratio of metal: salicylic acid.
- a light mineral oil may be added and then the hydrocarbon solvent, and any water formed may be removed by distillation.
- the resulting oil solution of the sulphurized product may be filtered, if desired, and then be added to an oil, such as a lubricating oil or a fuel oil, including gasoline.
- an oil such as a lubricating oil or a fuel oil, including gasoline.
- the product Before or after sulphurization the product may be reacted with a boron compound, such as boric acid, as described in the copending British patent application 8330441.
- a boron compound such as boric acid
- reaction products of this invention including mixtures thereof can be incorporated in oil compositions, in particular lubricating oil compositions or concentrates or fuels, e.g., automotive crankcase oils, in concentrations within the range of 0.001 to 65, in particular 0.1 to 15 %w based on the weight of the total compositions.
- the lubricating oils to which the additives of the invention can be added include not only mineral lubricating oils, but synthetic oils also. Synthetic hydrocarbon-lubricating oils may also be employed, as well as non-hydrocarbon synthetic oils including dibasic acid esters such as di-2-ethyl hexyl sebacate, carbonate esters, phosphate esters, halogenated hydrocarbons, polysilicones, polyglycols, glycol esters such as C 13 oxo acid diesters of tetraethylene glycol, etc. Mixtures of these oils, in particular of mineral lubricating oils, including hydrogenated oils, and synthetic lubricating oils, can also be used.
- additives may also be present, including dyes, pour point depressants, anti-wear, e.g., tricresyl phosphate, zinc dithiophasphates, antioxidants such as phenyl- alpha-naphthyl-amine, bis-phenols such as 4,4'-methylene bis (3,6-di-tert-butylphenol), viscosity index inprovers, such as hydrogenated (co)polymers of conjugated dienes and optionally styrene, ethylene-higher olefin copolymers, polymethylacrylates, polyisobutylene, and the like as well as ashless dispersants, such as reaction products of polyisobutylene, maleic anhydride and amines and/or polyols, or other metal-containing detergents, such as overbased metal salicylates.
- dyes e.g., tricresyl phosphate, zinc dithiophasphates
- antioxidants such as pheny
- Reaction products of amines, formaldehyde and alkyl phenols can also be present.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Carbonaceous Fuels (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848417298A GB8417298D0 (en) | 1984-07-06 | 1984-07-06 | Preparation of sulphurized overbased salicylates |
| GB8417298 | 1984-07-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0168110A1 true EP0168110A1 (de) | 1986-01-15 |
| EP0168110B1 EP0168110B1 (de) | 1988-09-28 |
Family
ID=10563524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP85201082A Expired EP0168110B1 (de) | 1984-07-06 | 1985-07-04 | Verfahren zur Herstellung von geschwefelten, überbasischen Salicylaten |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0168110B1 (de) |
| JP (1) | JPS6124561A (de) |
| BR (1) | BR8503202A (de) |
| CA (1) | CA1255691A (de) |
| DE (1) | DE3565258D1 (de) |
| GB (1) | GB8417298D0 (de) |
| SG (1) | SG6790G (de) |
| ZA (1) | ZA855047B (de) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2554825A1 (fr) * | 1983-11-15 | 1985-05-17 | Shell Int Research | Sel metallique basique borate et composition d'huile lubrifiante le contenant |
| US4876020A (en) * | 1987-06-25 | 1989-10-24 | Shell Oil Company | Lubricating oil composition |
| US6716817B1 (en) | 1993-02-19 | 2004-04-06 | Zentaris Ag | Method of treatment of female infertility |
| EP1754699A2 (de) * | 2005-07-29 | 2007-02-21 | Chevron Oronite S.A. | Schwefelarme metal detergenz-dispergiermittel. |
| WO2016124291A1 (en) * | 2015-02-06 | 2016-08-11 | Castrol Limited | Use of a hydrocarbyl-substituted salicylic acid detergent as an inhibitor of lead corrosion |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH059522Y2 (de) * | 1986-10-16 | 1993-03-09 |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2311931A (en) * | 1941-12-27 | 1943-02-23 | American Cyanamid Co | Lubricant |
| US2319662A (en) * | 1941-10-31 | 1943-05-18 | American Cyanamid Co | Lubricating oils |
| US2335017A (en) * | 1941-12-31 | 1943-11-23 | Standard Oil Dev Co | Lubricating composition |
| US2336074A (en) * | 1942-05-16 | 1943-12-07 | American Cyanamid Co | Lubricating oil |
| GB786167A (en) * | 1954-09-27 | 1957-11-13 | Shell Res Ltd | Improvements in or relating to the preparation of basic oil-soluble polyvalent metalsalts of organic acids and solutions of said basic salts in oils, and the resultingsalts |
| GB825315A (en) * | 1957-02-18 | 1959-12-16 | Socony Mobil Oil Co Inc | Complex carbonated metal salts of alkyl phenol sulphides |
| GB1194503A (en) * | 1965-08-23 | 1970-06-10 | Lubrizol Corp | Basic Sulfurised Salicylates and method for their preparation |
| US3595790A (en) * | 1969-10-22 | 1971-07-27 | Lubrizol Corp | Oil soluble highly basic metal salts of organic acids |
| GB1287812A (en) * | 1969-03-11 | 1972-09-06 | Lubrizol Corp | Basic, sulfurized salicylates and method for their preparation |
| US4221673A (en) * | 1977-01-28 | 1980-09-09 | Exxon Research & Engineering Co. | Metal phenates |
| US4320016A (en) * | 1979-09-24 | 1982-03-16 | Texaco Inc. | Carbon dioxide-blown overbased calcium alkylphenolate lubricating compositions |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2256441A (en) * | 1940-03-08 | 1941-09-16 | Socony Vacuum Oil Co Inc | Mineral oil composition and improving agent therefor |
| JPS60147497A (ja) * | 1984-01-09 | 1985-08-03 | Cosmo Co Ltd | サリチレ−トを含有する塩基性硫化アルカリ土類金属フエネ−ト型清浄剤の製造方法 |
| JPS60168793A (ja) * | 1984-02-13 | 1985-09-02 | Cosmo Co Ltd | 塩基性硫化アルカリ土類金属フエネ−ト型清浄剤の製造法 |
-
1984
- 1984-07-06 GB GB848417298A patent/GB8417298D0/en active Pending
-
1985
- 1985-06-17 CA CA000484252A patent/CA1255691A/en not_active Expired
- 1985-07-04 ZA ZA855047A patent/ZA855047B/xx unknown
- 1985-07-04 EP EP85201082A patent/EP0168110B1/de not_active Expired
- 1985-07-04 DE DE8585201082T patent/DE3565258D1/de not_active Expired
- 1985-07-04 JP JP14760685A patent/JPS6124561A/ja active Granted
- 1985-07-04 BR BR8503202A patent/BR8503202A/pt not_active IP Right Cessation
-
1990
- 1990-02-05 SG SG67/90A patent/SG6790G/en unknown
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2319662A (en) * | 1941-10-31 | 1943-05-18 | American Cyanamid Co | Lubricating oils |
| US2311931A (en) * | 1941-12-27 | 1943-02-23 | American Cyanamid Co | Lubricant |
| US2335017A (en) * | 1941-12-31 | 1943-11-23 | Standard Oil Dev Co | Lubricating composition |
| US2336074A (en) * | 1942-05-16 | 1943-12-07 | American Cyanamid Co | Lubricating oil |
| GB786167A (en) * | 1954-09-27 | 1957-11-13 | Shell Res Ltd | Improvements in or relating to the preparation of basic oil-soluble polyvalent metalsalts of organic acids and solutions of said basic salts in oils, and the resultingsalts |
| GB825315A (en) * | 1957-02-18 | 1959-12-16 | Socony Mobil Oil Co Inc | Complex carbonated metal salts of alkyl phenol sulphides |
| GB1194503A (en) * | 1965-08-23 | 1970-06-10 | Lubrizol Corp | Basic Sulfurised Salicylates and method for their preparation |
| GB1287812A (en) * | 1969-03-11 | 1972-09-06 | Lubrizol Corp | Basic, sulfurized salicylates and method for their preparation |
| US3595790A (en) * | 1969-10-22 | 1971-07-27 | Lubrizol Corp | Oil soluble highly basic metal salts of organic acids |
| US4221673A (en) * | 1977-01-28 | 1980-09-09 | Exxon Research & Engineering Co. | Metal phenates |
| US4320016A (en) * | 1979-09-24 | 1982-03-16 | Texaco Inc. | Carbon dioxide-blown overbased calcium alkylphenolate lubricating compositions |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2554825A1 (fr) * | 1983-11-15 | 1985-05-17 | Shell Int Research | Sel metallique basique borate et composition d'huile lubrifiante le contenant |
| US4876020A (en) * | 1987-06-25 | 1989-10-24 | Shell Oil Company | Lubricating oil composition |
| US6716817B1 (en) | 1993-02-19 | 2004-04-06 | Zentaris Ag | Method of treatment of female infertility |
| EP1754699A2 (de) * | 2005-07-29 | 2007-02-21 | Chevron Oronite S.A. | Schwefelarme metal detergenz-dispergiermittel. |
| EP1754699A3 (de) * | 2005-07-29 | 2007-04-25 | Chevron Oronite S.A. | Schwefelarme metal detergenz-dispergiermittel. |
| EP2295405A1 (de) | 2005-07-29 | 2011-03-16 | Chevron Oronite S.A. | Schwefelarme Metal Detergenz-Dispergiermittel |
| EP2316823A1 (de) | 2005-07-29 | 2011-05-04 | Chevron Oronite S.A. | Schwefelarme-Metall-detergenz-dispergiermittel |
| US7956022B2 (en) | 2005-07-29 | 2011-06-07 | Chevron Oronite Company Llc | Low sulfur metal detergent-dispersants |
| WO2016124291A1 (en) * | 2015-02-06 | 2016-08-11 | Castrol Limited | Use of a hydrocarbyl-substituted salicylic acid detergent as an inhibitor of lead corrosion |
| US10907111B2 (en) | 2015-02-06 | 2021-02-02 | Castrol Limited | Use of a hydrocarbyl-substituted salicylic acid detergent as an inhibitor of lead corrosion |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0168110B1 (de) | 1988-09-28 |
| CA1255691A (en) | 1989-06-13 |
| BR8503202A (pt) | 1986-03-25 |
| ZA855047B (en) | 1986-02-26 |
| JPS6124561A (ja) | 1986-02-03 |
| JPH0580518B2 (de) | 1993-11-09 |
| SG6790G (en) | 1990-07-13 |
| GB8417298D0 (en) | 1984-08-08 |
| DE3565258D1 (en) | 1988-11-03 |
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