EP0102255B1 - Procédé de préparation d'alkylphénates sulfurisés de métaux alcalino-terreux utilisables comme additifs pour huiles lubrifiantes - Google Patents
Procédé de préparation d'alkylphénates sulfurisés de métaux alcalino-terreux utilisables comme additifs pour huiles lubrifiantes Download PDFInfo
- Publication number
- EP0102255B1 EP0102255B1 EP83401269A EP83401269A EP0102255B1 EP 0102255 B1 EP0102255 B1 EP 0102255B1 EP 83401269 A EP83401269 A EP 83401269A EP 83401269 A EP83401269 A EP 83401269A EP 0102255 B1 EP0102255 B1 EP 0102255B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkaline
- glycol
- process according
- molar ratio
- alcohol
- 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
- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 98
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 49
- 239000003921 oil Substances 0.000 claims abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000654 additive Substances 0.000 claims abstract description 10
- -1 halide ions Chemical class 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000009835 boiling Methods 0.000 claims abstract description 7
- 239000013049 sediment Substances 0.000 claims abstract description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 6
- 238000006386 neutralization reaction Methods 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 238000010790 dilution Methods 0.000 claims description 11
- 239000012895 dilution Substances 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 8
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 5
- 239000002270 dispersing agent Substances 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 claims description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001110 calcium chloride Substances 0.000 claims description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical group [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 1
- 239000000920 calcium hydroxide Substances 0.000 claims 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
- 125000003916 ethylene diamine group Chemical group 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 20
- 229910052717 sulfur Inorganic materials 0.000 description 14
- 239000011593 sulfur Substances 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 10
- 229910052791 calcium Inorganic materials 0.000 description 8
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 6
- 235000011941 Tilia x europaea Nutrition 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 239000004571 lime Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000005987 sulfurization reaction Methods 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 0 *c(cc1S)ccc1O Chemical compound *c(cc1S)ccc1O 0.000 description 2
- IDQBJILTOGBZCR-UHFFFAOYSA-N 1-butoxypropan-1-ol Chemical compound CCCCOC(O)CC IDQBJILTOGBZCR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000010705 motor oil Substances 0.000 description 2
- 238000006479 redox reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
- WGKZYJXRTIPTCV-UHFFFAOYSA-N 2-butoxypropan-1-ol Chemical compound CCCCOC(C)CO WGKZYJXRTIPTCV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 235000001465 calcium Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000010710 diesel engine oil Substances 0.000 description 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical class [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- the present invention relates to a new process for the preparation of sulfurized alkylphenates of alkaline earth metals, especially calcium, of high alkalinity and the application of said sulfurized alkylphenates as detergent-dispersant additives for lubricating oils.
- the process for the preparation of sulfurized alkylphenate of alkaline earth metals of high alkalinity comprises the following steps:
- a simplified representation of the said mixture constituting the “sulfurized alkylphenol may be the following average formula: where X 'varies from 1 to 3 and generally from 1.4 to 2.5
- alkaline-earth bases mention may be made of calcium, barium or strontium oxides or hydroxides, and very particularly lime.
- the amount of dilution oil that can be used is such that the amount of oil contained in the final product represents from 25 to 65% by weight of said product and preferably from 30 to 50% by weight of said product.
- alkanols such as ethylhexanol, oxo alcohol, decyl alcohol, tridecyl alcohol
- alkoxyalkanols such as. 2-butoxyethanol, 2-butoxypropanol, dipropylene glycol methyl ether.
- halide ions are preferably CI- ions; these can be implemented via ammonium chloride or metal chlorides such as calcium chloride, zinc ...
- the neutralization operation is favorably carried out at a temperature between 120 and 180 ° C and preferably between 130 and 170 ° C at a pressure slightly lower than atmospheric pressure (930 10 2 Pa-96010 2 Pa).
- Said neutralization operation can also be carried out in the presence of an amine, according to a molar ratio of amine / alkaline earth base, which can range up to 0.2.
- an amine according to a molar ratio of amine / alkaline earth base, which can range up to 0.2.
- amines that can be used, there may be mentioned: polyalkyleneamines, such as polyethyleneamines and very particularly ethylenediamine and tris (3-oxa-6-amino-6 hexyl) amine.
- Said operation is also favorably carried out in the presence of acetic acid in an amount corresponding to a molar ratio of acetic acid / alkaline earth base which can range up to 0.2 and preferably up to 0.1.
- distillation operations succeeding the neutralization operation and the possible carbonation operation are carried out so as to remove water, glycol and alkanol.
- the carbonation operation is carried out at a temperature between 145 and 180 ° C at a pressure less than or equal to atmospheric pressure (93010 2 to 1010 10 2 Pa).
- the present invention also relates to a variant of the process described above, variant consisting in preparing "in situ in the neutralization medium the alkylphenolsulfurized from alkylphenol and sulfur.
- the quantity of sulfur used corresponds to a sulfur / alkylphenol molar ratio of between 0.8 and 2.
- the sulfurization-neutralization operation is favorably carried out at a temperature between 145 and 175 ° C and preferably between 155 and 170 ° C, optionally in the presence of an amine as above indicated for the general neutralization step.
- the carbonation operation is then carried out at a temperature between 155 and 180 ° C and preferably between 165 and 175 ° C, optionally in the presence of halide ions as above indicated.
- the present invention also relates to the product obtained according to the process described above as well as its application as an additive to improve the detergent and dispersing properties of lubricating oils.
- the amount of additive to be used depends on the future use of said oils. Thus for a petrol engine oil, the amount of additive to be added is generally between 1 and 2.5%; for a diesel engine oil it is generally between 1.8 and 4%, for a marine engine oil, this can go up to 30%.
- the lubricating oils which can thus be improved can be chosen from a wide variety of lubricating oils, such as naphthenic, paraffinic and mixed base lubricating oils, other hydrocarbon lubricants, for example lubricating oils derived from products. hard coal, and synthetic oils, for example alkylene polymers, oxide type polymers of alkylene and their derivatives, including polymers of alkylene oxide prepared by polymerizing alkylene oxide in the presence of water or alcohols, for example ethyl alcohol, esters of dicarboxylic acids , liquid esters of phosphorus acids, alkylbenzenes and dialkylbenzenes, polyphenyls, alkylbiphenylethers, polymers of silicon.
- lubricating oils such as naphthenic, paraffinic and mixed base lubricating oils, other hydrocarbon lubricants, for example lubricating oils derived from products. hard coal, and synthetic oils, for example alkylene polymers, oxide type polymers of alky
- Additional additives may also be present in said lubricating oils alongside the detergent-dispersants obtained according to the process of the invention; mention may, for example, be made of antioxidant, anti-corrosion additives, ashless dispersant additives.
- the product to be analyzed is diluted to a quarter in gasoline E (25 cm 3 of product to be analyzed + 75 cm 3 of gasoline E)
- the finished product is added to a SAE 50 oil with a paraffinic tendency so as to obtain a solution containing 25% of additive.
- glycol is added as a mixture with ethylhexanol or 2-butoxyethanol.
- the mixture is heated to 145 ° C., then it remains under a vacuum of 345 ⁇ 10 2 Pa for 30 minutes.
- a distillate D 1 is collected.
- the vacuum is gradually tightened to 66.5 10 2 Pa while heating up to 190 ° C. It remains for one hour at 190 ° C., then stripping is carried out with nitrogen for 1 hour at 190 ° C.
- the mixture is heated to 155 ° C. under slight depression (930 10 2 Pa), a first charge of alcohol consisting of a mixture of glycol and butoxyethanol or butoxypropanol is slowly added over 30 minutes, then a second charge of butoxyethanol or butoxypropanol alone in 40 minutes.
- a D1 distillate is collected.
- the vacuum is gradually tightened to 66.5 ⁇ 10 2 Pa.
- the mixture is heated to 190 ° C. for 1 hour, then a nitrogen stripping is carried out for 1 hour at 190 ° C.
- a D2 distillate is collected.
- Example 13 The operation described in Example 13 is carried out by introducing the mixture of 10 g of glycol and 10 g of butoxyethanol (1st charge) from the start (and not when the temperature reaches 155 ° C).
- Example 12 The operation described in Example 12 is carried out by introducing the 10 g of glycol at the start and then the 10 g of butoxyethanol at 155 ° C.
- Example 26 The operation described in Example 26 is carried out using a dodecylphenol containing 7% sulfur and an additional quantity of sulfur.
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)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Fats And Perfumes (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Manufacture And Refinement Of Metals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT83401269T ATE22112T1 (de) | 1982-06-24 | 1983-06-20 | Verfahren zur herstellung von sulfurierten erdalkalimetallalkylphenaten verwendbar als schmieroelzusatz. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8211060 | 1982-06-24 | ||
| FR8211060A FR2529226B1 (fr) | 1982-06-24 | 1982-06-24 | Procede de preparation d'alkylphenates sulfurises de metaux alcalino-terreux utilisables comme additifs pour huiles lubrifiantes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0102255A1 EP0102255A1 (fr) | 1984-03-07 |
| EP0102255B1 true EP0102255B1 (fr) | 1986-09-10 |
Family
ID=9275357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP83401269A Expired EP0102255B1 (fr) | 1982-06-24 | 1983-06-20 | Procédé de préparation d'alkylphénates sulfurisés de métaux alcalino-terreux utilisables comme additifs pour huiles lubrifiantes |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4514313A (pt) |
| EP (1) | EP0102255B1 (pt) |
| JP (1) | JPS5946262A (pt) |
| AT (1) | ATE22112T1 (pt) |
| AU (1) | AU557851B2 (pt) |
| BR (1) | BR8303347A (pt) |
| CA (1) | CA1182628A (pt) |
| DE (1) | DE3366063D1 (pt) |
| DK (1) | DK162398C (pt) |
| ES (1) | ES8403964A1 (pt) |
| FR (1) | FR2529226B1 (pt) |
| GB (1) | GB2123022B (pt) |
| GR (1) | GR78596B (pt) |
| MX (1) | MX26983A (pt) |
| PH (1) | PH19427A (pt) |
| PT (1) | PT76930B (pt) |
| ZA (1) | ZA834555B (pt) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1246615A (en) * | 1982-05-22 | 1988-12-13 | Charles Cane | Process for the production of alkaline earth metal alkyl phenates |
| FR2564830B1 (fr) * | 1984-05-25 | 1986-09-19 | Orogil | Procede de preparation d'alkylaryl sulfonates de metaux alcalino-terreux a partir d'acides alkylaryl sulfoniques lineaires et additifs detergents-dispersants pour huiles lubrifiantes ainsi obtenus |
| DE3676384D1 (de) * | 1985-08-13 | 1991-02-07 | Exxon Chemical Patents Inc | Ueberbasische zusaetze. |
| FR2587353B1 (fr) * | 1985-09-17 | 1987-11-20 | Orogil | Nouveaux additifs detergents-dispersants suralcalinises stables a l'hydrolyse pour huiles lubrifiantes et leur procede de preparation |
| US4776969A (en) * | 1986-03-31 | 1988-10-11 | Exxon Chemical Patents Inc. | Cyclic phosphate additives and their use in oleaginous compositions |
| NZ221128A (en) * | 1986-08-08 | 1989-09-27 | Chevron Res | Overbased sulphurised alkylphenols as lube oil additives |
| GB8621343D0 (en) * | 1986-09-04 | 1986-10-15 | Exxon Chemical Patents Inc | Overbased alkali metal additives |
| JPH04183792A (ja) * | 1990-11-19 | 1992-06-30 | Idemitsu Kosan Co Ltd | 過塩基性硫化アルカリ土類金属フェネート及びその用途 |
| GB9213723D0 (en) * | 1992-06-27 | 1992-08-12 | Bp Chemicals Additives | Process for the production of lubricating oil additives |
| US5292443A (en) * | 1992-08-21 | 1994-03-08 | Texaco Inc. | Process for producing neutralized sulfurized alkylphenate lubricant detergent additive |
| US5529705A (en) * | 1995-03-17 | 1996-06-25 | Chevron Chemical Company | Methods for preparing normal and overbased phenates |
| US5759966A (en) * | 1996-10-01 | 1998-06-02 | Chevron Chemical Company | High overbased metal sulfurized alkyphenates |
| US20030195126A1 (en) * | 2002-04-12 | 2003-10-16 | Boons Cornelis Hendrikus Maria | Carboxylated detergent-dispersant-containing compositions having improved properties in lubricating oils |
| US20040235682A1 (en) * | 2003-05-22 | 2004-11-25 | Chevron Oronite Company Llc | Low emission diesel lubricant with improved corrosion protection |
| US7163911B2 (en) * | 2003-05-22 | 2007-01-16 | Chevron Oronite Company Llc | Carboxylated detergent-dispersant additive for lubricating oils |
| US7435709B2 (en) * | 2005-09-01 | 2008-10-14 | Chevron Oronite Company Llc | Linear alkylphenol derived detergent substantially free of endocrine disruptive chemicals |
| US8399388B2 (en) | 2009-07-01 | 2013-03-19 | Chevron Oronite Company Llc | Low temperature performance lubricating oil detergents and method of making the same |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1382559A (fr) * | 1963-02-12 | 1964-12-18 | Lubrizol Corp | Compositions métalliques solubles dans les huiles et leur procédé de préparation |
| US3282835A (en) * | 1963-02-12 | 1966-11-01 | Lubrizol Corp | Carbonated bright stock sulfonates and lubricants containing them |
| US3493516A (en) * | 1966-05-04 | 1970-02-03 | Chevron Res | Carboxylate modified phenates |
| GB1144084A (en) * | 1966-08-24 | 1969-03-05 | Orobis Ltd | Improvements in or relating to lubricant additives |
| US3464970A (en) * | 1967-03-13 | 1969-09-02 | Maruzen Oil Co Ltd | Process for preparing over-based sulfurized calcium phenates |
| US3544463A (en) * | 1968-12-19 | 1970-12-01 | Mobil Oil Corp | Overbased oil-soluble metal salts |
| GB1280749A (en) * | 1970-06-18 | 1972-07-05 | Maruzen Oil Company Ltd | Process for preparation of over-based sulphurized phenates |
| US3936480A (en) * | 1971-07-08 | 1976-02-03 | Rhone-Progil | Additives for improving the dispersing properties of lubricating oil |
| BE786032A (fr) * | 1971-07-08 | 1973-01-08 | Rhone Progil | Nouveaux additifs pour huiles lubrifiantes |
| GB1470338A (en) * | 1974-05-17 | 1977-04-14 | Exxon Research Engineering Co | Lubricating oil compositions |
| GB1469289A (en) * | 1974-07-05 | 1977-04-06 | Exxon Research Engineering Co | Detergent additives |
| FR2300793A1 (fr) * | 1975-02-17 | 1976-09-10 | Orogil | Nouvelles compositions lubrifiantes |
| SU644811A1 (ru) * | 1975-07-14 | 1980-02-05 | Всесоюзный научно-исследовательский институт по переработке нефти | Способ получени сульфидалкилфенол тной присадки к смазочных маслам |
| US4016093A (en) * | 1976-03-19 | 1977-04-05 | Mobil Oil Corporation | Metal alkylphenate sulfides of reduced corrosiveness and method of preparing same |
| FR2355739A1 (fr) * | 1976-06-25 | 1978-01-20 | Thibault Jacques | Ensemble de traitement sur supports de colis de qualites differentes |
| US4222882A (en) * | 1978-02-08 | 1980-09-16 | Rhone-Poulenc Industries | Polymers bearing groups derived from N-substituted lactams and their use as lubricating oil additives |
| US4229308A (en) * | 1978-02-08 | 1980-10-21 | Rhone-Poulenc Industries | Polymer lubricating oil additives bearing nitrogen groups and their use as additives for lubricating oils |
| FR2416942A1 (fr) * | 1978-02-08 | 1979-09-07 | Orogil | Procede de preparation de detergents-dispersants de haute alcalinite pour huiles lubrifiantes |
| FR2429831A2 (fr) * | 1978-06-26 | 1980-01-25 | Orogil | Nouveau procede de preparation de detergents-dispersants de haute alcalinite pour huiles lubrifiantes |
| FR2450868A1 (fr) * | 1979-03-09 | 1980-10-03 | Orogil | Procede de preparation d'alkylphenates de magnesium et application des produits obtenus comme additifs detergents-dispersants pour huiles lubrifiantes |
-
1982
- 1982-06-24 FR FR8211060A patent/FR2529226B1/fr not_active Expired
-
1983
- 1983-03-21 MX MX26983A patent/MX26983A/es unknown
- 1983-06-20 AT AT83401269T patent/ATE22112T1/de not_active IP Right Cessation
- 1983-06-20 DE DE8383401269T patent/DE3366063D1/de not_active Expired
- 1983-06-20 EP EP83401269A patent/EP0102255B1/fr not_active Expired
- 1983-06-22 GR GR71755A patent/GR78596B/el unknown
- 1983-06-22 ZA ZA834555A patent/ZA834555B/xx unknown
- 1983-06-22 AU AU16125/83A patent/AU557851B2/en not_active Ceased
- 1983-06-23 CA CA000431110A patent/CA1182628A/fr not_active Expired
- 1983-06-23 GB GB08317023A patent/GB2123022B/en not_active Expired
- 1983-06-23 DK DK290083A patent/DK162398C/da not_active IP Right Cessation
- 1983-06-23 PT PT76930A patent/PT76930B/pt not_active IP Right Cessation
- 1983-06-23 ES ES523542A patent/ES8403964A1/es not_active Expired
- 1983-06-23 BR BR8303347A patent/BR8303347A/pt not_active IP Right Cessation
- 1983-06-24 PH PH29116A patent/PH19427A/en unknown
- 1983-06-24 US US06/507,804 patent/US4514313A/en not_active Expired - Lifetime
- 1983-06-24 JP JP58113000A patent/JPS5946262A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3366063D1 (en) | 1986-10-16 |
| DK162398B (da) | 1991-10-21 |
| EP0102255A1 (fr) | 1984-03-07 |
| FR2529226B1 (fr) | 1987-01-16 |
| GB8317023D0 (en) | 1983-07-27 |
| GB2123022A (en) | 1984-01-25 |
| ZA834555B (en) | 1984-03-28 |
| GB2123022B (en) | 1985-11-13 |
| BR8303347A (pt) | 1984-02-07 |
| FR2529226A1 (fr) | 1983-12-30 |
| PT76930B (fr) | 1986-03-11 |
| PT76930A (fr) | 1983-07-01 |
| DK290083D0 (da) | 1983-06-23 |
| ATE22112T1 (de) | 1986-09-15 |
| PH19427A (en) | 1986-04-15 |
| ES523542A0 (es) | 1984-04-01 |
| US4514313A (en) | 1985-04-30 |
| AU1612583A (en) | 1984-01-05 |
| CA1182628A (fr) | 1985-02-19 |
| DK290083A (da) | 1983-12-25 |
| GR78596B (pt) | 1985-09-27 |
| MX26983A (es) | 1994-03-31 |
| DK162398C (da) | 1992-03-23 |
| JPS6242957B2 (pt) | 1987-09-10 |
| AU557851B2 (en) | 1987-01-08 |
| ES8403964A1 (es) | 1984-04-01 |
| JPS5946262A (ja) | 1984-03-15 |
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