EP0101334B1 - Nouvel additif détergent-dispersant métallique de haute alcalinité pour huiles lubrifiantes - Google Patents
Nouvel additif détergent-dispersant métallique de haute alcalinité pour huiles lubrifiantes Download PDFInfo
- Publication number
- EP0101334B1 EP0101334B1 EP83401255A EP83401255A EP0101334B1 EP 0101334 B1 EP0101334 B1 EP 0101334B1 EP 83401255 A EP83401255 A EP 83401255A EP 83401255 A EP83401255 A EP 83401255A EP 0101334 B1 EP0101334 B1 EP 0101334B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- glycol
- additive according
- amine
- molar ratio
- amount
- 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
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- 239000000654 additive Substances 0.000 title claims abstract description 34
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 10
- 230000000996 additive effect Effects 0.000 title claims description 29
- 239000002270 dispersing agent Substances 0.000 title claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 78
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 39
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000011575 calcium Substances 0.000 claims abstract description 34
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 34
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 32
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000011777 magnesium Substances 0.000 claims abstract description 25
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 25
- 239000003921 oil Substances 0.000 claims abstract description 23
- 150000001412 amines Chemical class 0.000 claims abstract description 22
- 239000000395 magnesium oxide Substances 0.000 claims abstract description 20
- 239000013049 sediment Substances 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 238000010790 dilution Methods 0.000 claims description 13
- 239000012895 dilution Substances 0.000 claims description 13
- 239000008267 milk Substances 0.000 claims description 9
- 210000004080 milk Anatomy 0.000 claims description 9
- 235000013336 milk Nutrition 0.000 claims description 9
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims description 7
- 235000011941 Tilia x europaea Nutrition 0.000 claims description 7
- 239000004571 lime Substances 0.000 claims description 7
- 239000012429 reaction media Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- -1 ether amine Chemical class 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 229920002873 Polyethylenimine Polymers 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000000376 reactant Substances 0.000 claims 2
- JVUFOLHEAQXISM-UHFFFAOYSA-N 3-[2-[bis[2-(3-aminopropoxy)ethyl]amino]ethoxy]propan-1-amine Chemical group NCCCOCCN(CCOCCCN)CCOCCCN JVUFOLHEAQXISM-UHFFFAOYSA-N 0.000 claims 1
- 125000003916 ethylene diamine group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 9
- 150000004996 alkyl benzenes Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 6
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 5
- 239000000347 magnesium hydroxide Substances 0.000 description 5
- 235000012254 magnesium hydroxide Nutrition 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000005987 sulfurization reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JOONSONEBWTBLT-UHFFFAOYSA-N 2-tetradecylphenol Chemical class CCCCCCCCCCCCCCC1=CC=CC=C1O JOONSONEBWTBLT-UHFFFAOYSA-N 0.000 description 1
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000010710 diesel engine oil Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 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 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000010711 gasoline engine oil 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
- 239000007788 liquid Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 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
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 230000000063 preceeding effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/028—Overbased salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/26—Overbased carboxylic acid salts
- C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
-
- 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
- C10M2219/046—Overbased sulfonic acid salts
-
- 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
Definitions
- the present invention relates to a new metal detergent-dispersant additive of high alkalinity for lubricating oils.
- magnesium alkylbenzenesulfonate denotes any solution containing from 25 to 80% by weight, preferably from 30 to 70% by weight of a magnesium alkylbenzenesulfonate in a dilution oil which may or may not be the same as that implemented to prepare the new additive.
- magnesium alkylbenzenesulfonates which can be used, mention may be made of the magnesium salts of sulfonic acids obtained by sulfonation of alkylbenzenes derived from olefins or from C 15 -C 30 olefin polymers.
- the amount of dilution oil that can be used is such that the amount of oil contained in the final product (including that from the starting magnesium alkylbenzenesulfonate) represents from 20 to 60% by weight of said product, preferably from 25 to 55% and very particularly from 30 to 45% by weight of said product.
- sulfurized calcium alkylphenate denotes any solution containing from 25 to 70% by weight, preferably from 30 to 55% by weight of a sulfurized calcium alkylphenate in a dilution oil which may or may not be the same. than that used to prepare the new additive.
- sulfurized calcium alkylphenates which can be used, there may be mentioned: those obtained by the action of lime on a sulfurized alkylphenol preferably carrying one or more C 9 -C 30 alkyl substituents (and preferably Cg-C 22 ), such as nonyl, decyl, dodecyl or sulfurized tetradecylphenols possibly followed by carbonation; those obtained by sulfurization with sulfur of an alkylphenol preferably having one or more C 9 -C 30 alkyl substituents (preferably C 9 -C 22 ) in the presence of lime and glycol, optionally followed by carbonation.
- a sulfurized calcium alkylphenate characterized by a lime / alkylphenol molar ratio of between 0.2 and 2.5 and preferably between 0.4 and 2, and by a sulfur / alkylphenol molar ratio of between 1.1 and 2.2 and preferably between 1.3 and 1.8.
- active magnesium oxide denotes magnesium oxide MgO with a specific surface greater than or equal to 80 m 2 / g, for example between 100 and 170 m 2 / g.
- MgO magnesium oxide MgO with a specific surface greater than or equal to 80 m 2 / g, for example between 100 and 170 m 2 / g.
- Maglite DE with a specific surface area close to 140 m 2 / g marketed by Merck and“ Ferumag with a specific surface area close to 160 m 2 / g and marketed by Rhône-Poulenc.
- polyalkyleneamines such as polyethyleneamines and very particularly ethylenediamine
- etheramines and most particularly tris (3-oxa-6-amino hexyl) amine.
- the amine used may be present in “milk of magnesia from the start of the carbonation operation or during it.
- the carbonation operation is favorably carried out at a temperature which can range from 90 to 140 ° C. and preferably from 110 to 140 ° C., in one or more stages with the introduction of “milk of magnesia into the medium containing the magnesium alkylbenzenesulfonate , the sulfurized calcium alkylphenate and the dilution oil in one or more stages, each stage of introduction of "milk of magnesia being followed by a stage of carbonation. Said carbonation operation is carried out until the sediment level stabilizes; this lasts a maximum of 6 hours.
- a variant of the process making it possible to prepare the new additive consists in preceeding the carbonation operation with a step of precarbonation of the reaction medium consisting of magnesium alkylbenzene sulfonate, sulfurized calcium alkylphenate and oil dilution, in the presence of glycol and possibly sulfur.
- the new additive which is the subject of the invention has the advantage of being perfectly compatible with viscous oils, of containing a low rate of sediment and of being slightly viscous.
- the present invention also relates to the use of the new additive to improve the detergent, dispersing and anti-wear properties of lubricating oils.
- the amount of additive to be used depends on the future use of said oils.
- the amount of additive to be added is generally between 1 and 3.5%; for a diesel engine oil it is generally between 1.8 and 5%; for a marine engine oil, it can go up to 25%.
- 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.
- coal, and synthetic oils for example alkylene polymers, alkylene oxide type polymers and their derivatives, including alkylene oxide polymers prepared by polymerizing alkylene oxide to presence of water or alcohols, for example ethyl alcohol, esters of dicarboxylic acids, liquid esters of phosphorus acids, alkylbenzenes and dialkylbenzenes, polyphenyls, alkylbiphenyl ethers, polymers of silicon.
- Additional additives may also be present in said lubricating oils alongside the new additive of the invention; include, for example, anti-oxidant, anti-corrosion additives, ashless dispersant additives, etc.
- the reaction medium is heated for 30 minutes at 110 ° C at atmospheric pressure, then 30 minutes in vacuo so as to distill the reaction water.
- the mixture is heated to 120 ° C. for 2 hours (1 hour 30 minutes at atmospheric pressure and 30 minutes under a vacuum of 120 10 2 Pa), then the vacuum is broken.
- Milk of magnesia is prepared in a beaker by mixing, with stirring, active magnesium oxide, glycol and an amine.
- This milk is divided into three relatively equal fractions.
- the flask is gradually placed under vacuum (40 10 2 Pa) and then heated for 2 hours at 200 ° C.
- This test is carried out by adding 10% by weight of product to be tested to a SAE 30 mineral oil, storing the solution obtained for 1 month at 20 ° C. and studying the appearance of the solution as a function of time.
- the finished product is added to an SAE 50 oil with a paraffinic tendency so as to obtain a solution containing 125 millimoles of calcium + magnesium.
- the solution is stored for 24 hours and then centrifuged under the following conditions: then measure the sediment rate.
- Example 2 The operations described in Example 1 are repeated, replacing the 16.5 g of ethylenediamine with 8 g of tris (3-oxa-6-amino-hexyl) amine called "TOA".
- Example 1 The operations described in Example 1 are repeated, carrying out the start of the carbonation step at 130 ° C. instead of 110 ° C.
- the mixture is heated to 110 ° C. and 112 g of glycol are charged in 1 hour.
- the reactor is placed under vacuum.
- the vacuum is broken, the heating is stopped and carbonated for 1 hour at a rate of 0.5 g / min.
- a mixture of 129 g of MgO and 349 g of glycol is prepared in a beaker, which mixture is introduced into the reactor over 5 minutes.
- C0 2 is introduced into the medium. Two hours later, 16.5 g of ethylenediamine are introduced, then two hours more after 85 g of water, then carbonation is continued for a further 2 hours.
- the medium is distilled for 2 hours at 200 ° C under 40 10 2 Pa.
- The% of raw sediment is 2.3.
- Example 12 The operations described in Example 12 are repeated in the absence of ethylenediamine.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Detergent Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT83401255T ATE30716T1 (de) | 1982-06-24 | 1983-06-17 | Metallenthaltender detergens-dispergierzusatz von hoher alkalitaet fuer schmieroele. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8211059A FR2529225B1 (fr) | 1982-06-24 | 1982-06-24 | Nouvel additif detergent-dispersant metallique de haute alcalinite pour huiles lubrifiantes |
| FR8211059 | 1982-06-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0101334A2 EP0101334A2 (fr) | 1984-02-22 |
| EP0101334A3 EP0101334A3 (en) | 1985-10-09 |
| EP0101334B1 true EP0101334B1 (fr) | 1987-11-11 |
Family
ID=9275356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP83401255A Expired EP0101334B1 (fr) | 1982-06-24 | 1983-06-17 | Nouvel additif détergent-dispersant métallique de haute alcalinité pour huiles lubrifiantes |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4470916A (enExample) |
| EP (1) | EP0101334B1 (enExample) |
| JP (1) | JPS6025079B2 (enExample) |
| AT (1) | ATE30716T1 (enExample) |
| AU (1) | AU559589B2 (enExample) |
| BR (1) | BR8303369A (enExample) |
| CA (1) | CA1182627A (enExample) |
| DE (1) | DE3374403D1 (enExample) |
| DK (1) | DK289983A (enExample) |
| ES (1) | ES8403963A1 (enExample) |
| FR (1) | FR2529225B1 (enExample) |
| GB (1) | GB2123023B (enExample) |
| GR (1) | GR78595B (enExample) |
| PH (1) | PH19405A (enExample) |
| PT (1) | PT76929B (enExample) |
| SG (1) | SG54685G (enExample) |
| ZA (1) | ZA834558B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4614602A (en) * | 1985-05-01 | 1986-09-30 | Amoco Corporation | Lubricant overbased detergent-dispersants with improved solubility |
| FR2588269B1 (fr) * | 1985-10-03 | 1988-02-05 | Elf France | Procede de preparation d'additifs surbases tres fluides et a basicite elevee et composition contenant lesdits additifs |
| US4664822A (en) * | 1985-12-02 | 1987-05-12 | Amoco Corporation | Metal-containing lubricant compositions |
| US4767551A (en) * | 1985-12-02 | 1988-08-30 | Amoco Corporation | Metal-containing lubricant compositions |
| GB8723909D0 (en) * | 1987-10-12 | 1987-11-18 | Exxon Chemical Patents Inc | Lubricant oil additive |
| JP3112569B2 (ja) * | 1992-06-25 | 2000-11-27 | ジヤトコ・トランステクノロジー株式会社 | 自動変速機の変速制御装置 |
| US7084092B2 (en) * | 2003-08-25 | 2006-08-01 | M-I L.L.C. | Shale hydration inhibition agent and method of use |
| CN113186015B (zh) * | 2021-02-02 | 2024-02-06 | 安徽澳润新材料有限公司 | 一种高碱值磺酸镁清净剂及其制备方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1605316A (en) * | 1925-05-19 | 1926-11-02 | Guiberson Corp | Pump-rod guide |
| US3282835A (en) * | 1963-02-12 | 1966-11-01 | Lubrizol Corp | Carbonated bright stock sulfonates and lubricants containing them |
| 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 |
| GB1280749A (en) * | 1970-06-18 | 1972-07-05 | Maruzen Oil Company Ltd | Process for preparation of over-based sulphurized phenates |
| GB1399092A (en) * | 1971-05-27 | 1975-06-25 | Cooper & Co Ltd Edwin | Lubricant additives |
| BE786032A (fr) * | 1971-07-08 | 1973-01-08 | Rhone Progil | Nouveaux additifs pour huiles lubrifiantes |
| US3936480A (en) * | 1971-07-08 | 1976-02-03 | Rhone-Progil | Additives for improving the dispersing properties of lubricating oil |
| 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 |
| US4016093A (en) * | 1976-03-19 | 1977-04-05 | Mobil Oil Corporation | Metal alkylphenate sulfides of reduced corrosiveness and method of preparing same |
| 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 |
| FR2416942A1 (fr) * | 1978-02-08 | 1979-09-07 | Orogil | Procede de preparation de detergents-dispersants de haute alcalinite pour huiles lubrifiantes |
| 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 |
| FR2429832A1 (fr) * | 1978-06-26 | 1980-01-25 | Orogil | Procede perfectionne de preparation d'additifs detergents-dispersants, metalliques de haute alcalinite notamment 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 |
| FR2429833A1 (fr) * | 1978-06-26 | 1980-01-25 | Orogil | Procede de preparation de detergents-dispersants metalliques suralcalinises 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 FR8211059A patent/FR2529225B1/fr not_active Expired
-
1983
- 1983-06-17 DE DE8383401255T patent/DE3374403D1/de not_active Expired
- 1983-06-17 EP EP83401255A patent/EP0101334B1/fr not_active Expired
- 1983-06-17 AT AT83401255T patent/ATE30716T1/de not_active IP Right Cessation
- 1983-06-22 US US06/506,774 patent/US4470916A/en not_active Expired - Lifetime
- 1983-06-22 AU AU16124/83A patent/AU559589B2/en not_active Ceased
- 1983-06-22 GR GR71754A patent/GR78595B/el unknown
- 1983-06-22 ZA ZA834558A patent/ZA834558B/xx unknown
- 1983-06-23 ES ES523539A patent/ES8403963A1/es not_active Expired
- 1983-06-23 BR BR8303369A patent/BR8303369A/pt not_active IP Right Cessation
- 1983-06-23 PT PT76929A patent/PT76929B/pt unknown
- 1983-06-23 GB GB08317024A patent/GB2123023B/en not_active Expired
- 1983-06-23 DK DK289983A patent/DK289983A/da not_active Application Discontinuation
- 1983-06-23 CA CA000431109A patent/CA1182627A/fr not_active Expired
- 1983-06-24 PH PH29119A patent/PH19405A/en unknown
- 1983-06-24 JP JP58112999A patent/JPS6025079B2/ja not_active Expired
-
1985
- 1985-07-16 SG SG546/85A patent/SG54685G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE30716T1 (de) | 1987-11-15 |
| AU1612483A (en) | 1984-01-05 |
| SG54685G (en) | 1986-05-02 |
| JPS5947299A (ja) | 1984-03-16 |
| FR2529225B1 (fr) | 1986-04-25 |
| EP0101334A2 (fr) | 1984-02-22 |
| ES523539A0 (es) | 1984-04-01 |
| GB2123023A (en) | 1984-01-25 |
| PT76929A (fr) | 1983-07-01 |
| GB8317024D0 (en) | 1983-07-27 |
| BR8303369A (pt) | 1984-02-07 |
| CA1182627A (fr) | 1985-02-19 |
| ES8403963A1 (es) | 1984-04-01 |
| GB2123023B (en) | 1985-06-05 |
| EP0101334A3 (en) | 1985-10-09 |
| US4470916A (en) | 1984-09-11 |
| AU559589B2 (en) | 1987-03-12 |
| DK289983A (da) | 1983-12-25 |
| FR2529225A1 (fr) | 1983-12-30 |
| DE3374403D1 (en) | 1987-12-17 |
| JPS6025079B2 (ja) | 1985-06-15 |
| PT76929B (fr) | 1986-01-27 |
| DK289983D0 (da) | 1983-06-23 |
| GR78595B (enExample) | 1984-09-27 |
| PH19405A (en) | 1986-04-10 |
| ZA834558B (en) | 1984-03-28 |
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