Classifications

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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
  • C10M173/00—Lubricating compositions containing more than 10% water
  • C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
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  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
  • C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
  • C08G65/2633—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen the other compounds containing amide groups
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  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/329—Polymers modified by chemical after-treatment with organic 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
  • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
  • C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
  • C10M105/68—Amides; Imides
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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
  • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
  • C10M105/72—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing sulfur, selenium or tellurium
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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
  • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
  • C10M105/74—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing phosphorus
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
  • C11D1/38—Cationic compounds
  • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
  • C11D1/526—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 are polyalkoxylated
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
  • C10M2215/0806—Amides [having hydrocarbon substituents containing less than thirty carbon atoms] used as base material
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
  • C10M2215/082—Amides [having hydrocarbon substituents containing less than thirty carbon atoms] containing hydroxyl groups; Alkoxylated derivatives
• • 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
  • C10M2219/0406—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides used as base material
• • 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
  • C10M2219/042—Sulfate esters
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • 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
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
  • C10M2223/04—Phosphate esters
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
  • C10M2223/04—Phosphate esters
  • C10M2223/0405—Phosphate esters used as base material
• • 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
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/04—Detergent property or dispersant property
• • 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
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
• • 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
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/20—Metal working
• • 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
  • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
  • C10N2060/06—Chemical after-treatment of the constituents of the lubricating composition by epoxydes or oxyalkylation reactions
• • 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
  • C10N2070/00—Specific manufacturing methods for lubricant compositions
• • 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
  • C10N2070/00—Specific manufacturing methods for lubricant compositions
  • C10N2070/02—Concentrating of additives

Definitions

• the present invention relates to polyalkoxylated superamides, optionally functionalized. More particularly, it relates to superamides comprising a block derived from propylene oxide, then a block derived from ethylene oxide.
• the present invention likewise relates to their use as an emulsifying agent, preferably oils.
• amides denotes the family of alkanolamides obtained by transamidation of a fatty acid ester. There are alkanolamides obtained by amidation of a fatty acid. They are however obtained in the form of a mixture comprising the amide, the amine, the fatty acid, and the water. Typically, the amide concentration is 60-65%.
• the final mixture contains more than 90% of superamides, which constitutes an obvious advantage.
• the alcohol from the fatty acid ester used is distilled during the course of the reaction, making the latter complete.
• R 1 represents a C -C 22 hydrocarbon radical. linear or branched, saturated or not, optionally carrying at least one hydroxyl group,
• R 2 represents a hydrogen atom or a CC 4 hydrocarbon radical
• R 3 represents a hydrogen atom or a CC 4 hydrocarbon radical
• R 4 and R 5 which may or may not be identical, represent a hydrogen atom or an alkyl radical comprising 1 or 2 carbon atoms, provided that at most one of these two radicals is a hydrogen atom,
• X represents a hydrogen atom, a C- ⁇ -C- 6 hydrocarbon radical, a phosphate, carboxylate, sulfate, sulfonate group, m is an average number between 0 excluded and 20, n is an average number between 0 excluded and 50, p is 1 or 2, depending on the nature of X.
• the radical R 1 is more particularly a hydrocarbon radical, linear or branched, saturated or not, of C-10-C22. optionally carrying at least one hydroxyl group.
• said radical comprises at least one ethylenic unsaturation.
• the radical R 1 is more precisely derived from fatty acids or oils of animal or vegetable origin.
• saturated C10-C22 fatty acids examples include lauric, capric, decanoic, stearic, isostearic, gadoleic, myristic acids, or mixtures thereof.
• C10-C22 fatty acids carrying at least one ethylenic unsaturation there may be mentioned, without intending to be limited thereto, linderic, myristoleic, palmitoleic, oleic, petroselenic, doeglic, erucic, linoleic and linolenic acids. , isanic, stearodonic, arachidonic, chypanodonic, ricinoleic, or mixtures thereof.
• the radical R 1 derives more particularly from fatty acids chosen from palmitoleic, oleic, petroselenic, erucic, linoleic, linolenic, ricinoleic acids, or their mixtures.
• oils from which the radical R 1 is derived mention may be made of oils of animal or vegetable origin.
• oils of animal origin mention may be made, among others, of sperm whale, dolphin, whale, seal, sardine, herring, shark, cod liver oils; beef feet as well as beef, pork, horse and mutton fats (tallow).
• oils of vegetable origin there may be mentioned, among others, rapeseed, sunflower, peanut, olive, walnut, corn, soybean, flax, hemp, grapeseed, copra, palm, seed oils. of cotton, babassu, jojoba, sesame, castor, coriander. Rapeseed oil is preferred.
• R1 can be derived from products resulting from alcoholysis reactions, more precisely from methanolysis, from the abovementioned oils.
• radicals R 2 and R 3 identical or not, represent a hydrogen atom or a hydrocarbon radical in CC 4 , which is more particularly saturated.
• the radicals R 2 and R 3 represent a hydrogen atom, the methyl, ethyl, propyl and isomers, butyl and isomers radicals.
• radicals R 4 and R 5 are more preferably chosen from hydrogen or the methyl radical, on the condition that at least one of the two radicals, but not both simultaneously, represents a hydrogen atom.
• this motif is derived from propylene oxide.
• the coefficient m representing an average number, varies between 0 excluded and 20. Preferably this coefficient is between 0 excluded and 10.
• the coefficient n representing an average number, varies between 1 and 50, more particularly between 1 and 20.
• the compounds according to the present invention can be in a nonionic or ionic form.
• the radical X represents a hydrogen atom, or a C-
• the value of the coefficient p is 1.
• the superamides are in an ionic form.
• a first variant of this possibility corresponds to compounds for which X represents a phosphate function.
• X represents a phosphate function.
• A represents Ri-CONR2-CH 2 CHR30- (CHR4-CHR50) m - (CH 2 CH 2 O) n - R1, R, R3, R4, R5_ m and n being defined previously,
• a second variant of this possibility corresponds to compounds for which X represents a carboxylate function of formula - (CH2) ⁇ -COOM, in which:
• M has the same definition as before, r is equal to 1 or 2.
• the compounds according to the invention comprise a radical X defined by the following formula -SO 3 M, in which M is defined as above.
• the compounds according to the invention comprise a radical X defined by the following formula - (CH2) s -SO 3 M, formula in which M has the same meaning as above, and s is equal to 2 or 3.
• the process for preparing the superamides as described above consists in implementing the following steps: (a) reacting, on the one hand, a fatty acid ester, the part relating to the acid is a C7-C22 hydrocarbon radical. linear or branched, saturated or not, optionally carrying at least one hydroxyl group; the part relating to alcohol, a C-1-C4 hydrocarbon radical, with, on the other hand, an alkanolamine of formulas NH 2 R 2 -CH 2 -CHR 3 -OH or NH- (CH 2 -CHR 3 -OH) 2 , optionally in the presence of a basic compound.
• step (b) the product obtained at the end of step (a) is reacted with a compound of formula: HR4C-CR5H
• R4 and R 5 being defined as above,
• step (c) the product obtained at the end of step (b) is reacted with ethylene oxide
• step (d) optionally, a step of functionalization of the compound obtained during step (c) is carried out with the aim of replacing the terminal hydrogen atom with a hydrocarbon radical, a phosphate, carboxylate, sulfate or sulfonate function; the proportions of the various reagents used are such that the formulas (I) or (II) are satisfied.
• Step (a) is carried out in the presence of a fatty acid ester or a mixture of such esters.
• a fatty acid ester or a mixture of such esters The fatty acids described during the definition of the radical R 1 can be used and the list will not be repeated here.
• the alcohol part of the ester used as reactant in step (a) this is derived from an alcohol, preferably C-
• this first step can advantageously be carried out using products resulting from alcoholysis reactions (methanolysis more particularly) of oils of animal or vegetable origin, in particular chosen from those mentioned above.
• alkanolamines suitable for implementing the process there may be mentioned in particular, monoethanolamine, diethanolamine, isopropylamine, diisopropylamine, methylethanolamine, ethylethanolamine.
• monoethanolamine is preferably used.
• Step (a) can be carried out with or without the presence of a basic catalyst.
• a basic catalyst Preferably, such a compound is used.
• the latter is more particularly chosen from alkali metal alcoholates, such as sodium methylate, sodium ethylate, potassium methylate, potassium ethylate. It is likewise possible to use alkali metal hydroxides such as soda or potash; alkali metal carbonates, such as sodium carbonate, potassium carbonate.
• the amount of this catalyst if present, usually varies between 0.01 and 5% by weight relative to the superamide.
• the reaction temperature is generally between 50 and 150 ° C. It is advantageously higher than the boiling point of the alcohol produced during the reaction, so as to eliminate the alcohol as soon as it appears in the mixture.
• step (b) is implemented. It should be noted that a step of purifying the product obtained is not compulsory.
• Step (b) therefore consists in bringing the amide obtained previously into contact with the alkylene oxide of formula: HR4C-CR5H
• the alkylene oxide is propylene oxide.
• the reaction is carried out more particularly under basic conditions, for example by using a basic catalyst of the type used in step (a). It is likewise conceivable to carry out said reaction in the presence of a Lewis acid, such as titanium trichloride, boron trifluoride.
• a Lewis acid such as titanium trichloride, boron trifluoride.
• the number of moles of alkylene oxide introduced is such that it allows access to an alkoxylated superamide whose coefficient m corresponds to the values indicated above.
• the temperature at which the reaction is carried out usually varies between 80 and
• reaction conditions nitrogen for example.
• a solvent for example, a compound which are inert under the reaction conditions.
• suitable compounds mention may in particular be made of aromatic or non-aromatic hydrocarbon solvents, such as hexane, toluene, xyiene.
• halogenated solvents such as chloroform, as well as solvents of the cyclic ether type or not, such as dibutylether, tetrahydrofuran.
• the product obtained at the end of this step (b) is advantageously brought into contact, without intermediate purification (this is indeed not necessary) with ethylene oxide.
• the number of moles of ethylene oxide introduced is such that it gives access to an alkoxylated / ethoxylated superamide whose coefficient n corresponds to the values indicated in formulas (I) and (II).
• steps (b) and (c) are carried out under basic conditions. More particularly, the quantity of base necessary for the two stages is added at the start of the first stage. Usually, the base content varies between 0.5% and 0.7% by weight relative to the initial superamide, used in steps (b) and then (c).
• step (c) it is preferable to neutralize the excess base remaining in the medium.
• the reaction medium is brought into contact with an acid which can be chosen from organic acids, such as carboxylic acids, more particularly acetic acid, for example; such as sulfonic acids, such as dodecylbenzene sulfonic acid. It is likewise possible to use a mineral acid, such as hydrochloric acid, sulfuric acid.
• the amount of acid used is such that the pH of a mixture comprising 5 g of product, supplemented with 45 g of ethanol and 50 g of water is between 8 and 11.
• the product obtained is a superamide comprising two oxylalkylenated blocks, the first being an oxyalkylenated block comprising at least one radical different from hydrogen (preferably oxypropylenated) then an oxyethylenated block.
• the radical X is hydrogen.
• a compound of formula R-Hal is brought into contact, in which R represents a C - ⁇ - C Q hydrocarbon radical, preferably saturated, Hal represents a halogen atom, preferably chlorine, bromine.
• the product from step (c) is brought into contact with a reagent of the phosphoric acid, polyphosphoric acid, anhydride type. phosphoric, phosphorus oxychloride.
• step (c) the product obtained during step (c) is brought into contact with sulfur trioxide, sulfuric acid or oleum, chlorosulfonic acid, sulfamic acid.
• the polyoxyalkylenated superamide according to the present invention finds numerous applications. Indeed, it has anti-corrosion, lubrication and emulsification properties. Thus, the polyoxyalkylenated superamide can be used as an emulsifying agent for fluids comprising immiscible or little miscible phases with each other.
• the superamide according to the invention exhibits very advantageous emulsification properties if one of the abovementioned phases is an oil or an oil derivative, or else a fatty acid ester, these compounds possibly being present alone. mixed.
• the oils can be chosen from organic oils, of animal or vegetable origin, or even mineral oils.
• oils of animal origin mention may be made, among others, of sperm whale, dolphin, whale, seal, sardine, herring, shark, cod liver oils.
• oils of vegetable origin there may be mentioned, among others, rapeseed, sunflower, peanut, olive, walnut, corn, soybean, flax, hemp, grapeseed, copra, palm, seed oils. of cotton, babassu, jojoba, sesame, castor, coriander.
• oils As an derivative of oils, mention may be made of alcoholysis products, more specifically methanolysis, of oils.
• the esters whose acid part derives from fatty acids are a hydrocarbon radical, linear or branched, saturated or not, of C7-C22. preferably in C-10-C22. optionally carrying at least one hydroxyl group, and the alcohol part of which derives from alcohol comprising a hydrocarbon radical, linear or branched, saturated or not, of C1-C10.
• the fatty acids listed above are suitable, they will not be repeated in this part.
• the methyl, ethyl, propyl and butyl esters can in particular be used.
• the polyoxypropylenated - polyoxyethylenated superamides have oil emulsifying properties, while the homologous compounds carrying polyoxyethylenated - polyoxypropylenated blocks do not have such a property.
• the superamides according to the invention have anticorrosion agent properties.
• the compounds according to the invention do not contain free fatty acid and / or free amines, which represents an advantage for certain applications.
• the numerous fields of application of the superamides according to the invention there may be mentioned, without intending, however, to be limited to:
• - textile in particular as a lubricant in the spinning operations of the textile fiber, or even as an emulsifier for mineral oils or silicone anti-foams;
• - elastomers processing aid
• - phytosanitary as an emulsifier for all phytosanitary formulations
• the fluids used in this application are well known. They are usually in the form of emulsions or concentrated microemulsions which are subsequently diluted by the user. They can also be in the form of emulsifiable concentrates put into emulsion by the user.
• These fluids preferably comprise an oil, a derivative or even a fatty acid ester, as a phase little or immiscible in water.
• the organic, mineral oils, their derivatives as well as the fatty acid esters mentioned above can be used in this application as appropriate.
• oils are used. To simplify the text, we will use for what follows the term oil to designate all these compounds.
• the oil content can vary within wide limits. It can thus represent up to 90% by weight of the concentrate. Preferably, the water content varies between 0 excluded and 50% by weight.
• the water content usually varies between 0 excluded and 50% by weight of the fluid.
• the content of polyoxyalkylenated superamides according to the invention varies more particularly between 0 excluded and 40% by weight of the fluid.
• the fluids can optionally comprise other emulsifying agents.
• emulsifying agents which can be used, mention may be made of nonionic, anionic surfactants.
• the content of these compounds usually varies between 0 and 30% by weight of the fluid.
• the fluids can also comprise conventional lubrication additives, such as for example fatty acids such as those mentioned previously as well as esters of these fatty acids.
• Extreme pressure additives can also be used, which are compounds based on chlorine, sulfur, phosphorus, or combinations thereof. Note that these fluids may also include conventional additives such as polymeric esters.
• the fluids can also comprise one or more anti-corrosion agents chosen, for example, from amines, alkanolamines, azoles, carboxylates, amine borates and boroalkanolamides.
• Said fluids can likewise include biocides, bactericides, anti-foaming agents, coupling agents (such as alcohols and glycols).
• the content of these compounds usually varies between 0 and 20% by weight.
• polyoxyalkylenated superamides have, for the family in general, properties of oil emulsifying agent, of anti-corrosion agents, certain functionalized polyoxyalkylenated superamides have additional properties.
• the alkanolamides according to the invention in the case where the radical X is a phosphate, have anti-wear properties.
• alkanolamides for which the radical X is a carboxylate they have very advantageous dispersing properties, in particular in the presence of fatty acids in the form of alkaline earth metal salts (soaps) or of precipitates.
• Rapeseed oil methyl esters are introduced into a reactor and then monoethanolamine is added (ester / monoethaneamine molar ratio: 1/1, 025). Then concentrated sodium hydroxide (0.1% by weight relative to the superamide obtained) is added.
• the temperature is about 140 ° C and the reaction is carried out under nitrogen.
• the reaction time is approximately 6 hours. During the reaction, the methanol is distilled.
• the reaction is monitored by measuring the amine index.
• the reaction is stopped with an index of less than 15 mg of KOH / g of product. Excess unreacted alkanolamine is vacuum distilled and the mixture is then cooled.
• the superamide obtained previously is melted and introduced into a reactor. 0.2% of potassium hydroxide is then added thereto (the percentage is expressed by weight relative to the superamide; the potassium is 50%).
• the mixture is heated at 120 ° C under vacuum for 1 hour.
• the reactor is then purged and placed under nitrogen.
• the reaction mixture is stripped under vacuum.
• the mixture is then heated to 150 ° C. and propylene oxide (3 moles) is added and the whole is kept at the same temperature for 1 hour.
• reaction mixture is then cooled to 70 ° C and stripped in vacuo for one hour.
• the excess base present in the product obtained is neutralized by adding acetic acid. At the end of this process, a liquid is recovered.
• the emulsifying power is evaluated as follows:
• Oil 1 paraffinic mineral oil: Neutral oil 100 sold by Mobil Oil 2: naphthenic mineral oil: Catenex N 912 sold by Shell.
• a test of stability over time of the mixtures comprising the superamide according to the invention was carried out, at 20 ° C and 40 ° C (measurement of the creaming height after a given time).
• the mixture was not destabilized. Indeed, the creaming height is zero after 24 hours, at 20 and 40 ° C.

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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Chemistry (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• General Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Polymers & Plastics (AREA)
• Medicinal Chemistry (AREA)
• Wood Science & Technology (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Lubricants (AREA)
• Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
• Polyethers (AREA)
• Preventing Corrosion Or Incrustation Of Metals (AREA)
• Detergent Compositions (AREA)
• Polysaccharides And Polysaccharide Derivatives (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

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• 1999
  • 1999-09-09 FR FR9911295A patent/FR2798387B1/fr not_active Expired - Fee Related
• 2000
  • 2000-09-11 KR KR10-2002-7003160A patent/KR100504521B1/ko not_active Expired - Fee Related
  • 2000-09-11 EP EP00962601A patent/EP1218438B1/fr not_active Expired - Lifetime
  • 2000-09-11 CA CA002384322A patent/CA2384322C/fr not_active Expired - Fee Related
  • 2000-09-11 US US10/070,367 patent/US6689908B1/en not_active Expired - Lifetime
  • 2000-09-11 CN CNB008126534A patent/CN1239572C/zh not_active Expired - Lifetime
  • 2000-09-11 AT AT00962601T patent/ATE275596T1/de not_active IP Right Cessation
  • 2000-09-11 BR BRPI0013891-6A patent/BR0013891B1/pt not_active IP Right Cessation
  • 2000-09-11 JP JP2001522311A patent/JP4020641B2/ja not_active Expired - Lifetime
  • 2000-09-11 WO PCT/FR2000/002502 patent/WO2001018092A1/fr not_active Ceased
  • 2000-09-11 ES ES00962601T patent/ES2225216T3/es not_active Expired - Lifetime
  • 2000-09-11 MX MXPA02002510A patent/MXPA02002510A/es active IP Right Grant
  • 2000-09-11 AU AU74268/00A patent/AU755076B2/en not_active Expired
  • 2000-09-11 DE DE60013618T patent/DE60013618T2/de not_active Expired - Lifetime

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