EP2954035B1 - Procédé de préparation de graisse à base d'urée - Google Patents

Procédé de préparation de graisse à base d'urée Download PDF

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EP2954035B1
EP2954035B1 EP14703097.7A EP14703097A EP2954035B1 EP 2954035 B1 EP2954035 B1 EP 2954035B1 EP 14703097 A EP14703097 A EP 14703097A EP 2954035 B1 EP2954035 B1 EP 2954035B1
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Prior art keywords
formula
compound
grease
carbon atoms
urea
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German (de)
English (en)
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EP2954035A1 (fr
Inventor
Stefan Daegling
Alexander HELLAWELL
Eurydice KONE
Alexander Massey
Howard Brian Mead
Don VAN ZWIETEN
Ton Visser
Robert James Wilkinson
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Shell Internationale Research Maatschappij BV
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Shell Internationale Research Maatschappij BV
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • 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
    • C10M115/00—Lubricating compositions characterised by the thickener being a non-macromolecular organic compound other than a carboxylic acid or salt thereof
    • C10M115/08—Lubricating compositions characterised by the thickener being a non-macromolecular organic compound other than a carboxylic acid or salt thereof containing nitrogen
    • 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
    • C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
    • 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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/02—Mixtures of base-materials and thickeners
    • 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
    • C10M2215/10—Amides of carbonic or haloformic acids
    • C10M2215/102—Ureas; Semicarbazides; Allophanates
    • C10M2215/1026—Ureas; Semicarbazides; Allophanates used as thickening 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy
    • 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

Definitions

  • the invention relates to a process for preparing a urea grease.
  • Urea greases are used in a variety of applications including bearings for constant-velocity joints, ball joints, wheel bearings, alternators, cooling fans, ball screws, linear guides of machine tools, sliding areas of construction equipment, and bearings and gears in steel equipment and various other industrial mechanical facilities.
  • Urea greases typically have excellent heat and oxidation resistance, and can extend the lifetime of bearings.
  • Urea greases contain low molecular weight organic compounds, sometimes referred to as polyureas, that are typically synthesized from isocyanates and amines.
  • a diisocyanate and a monoamine can be used to form a diurea:
  • a diisocyanate and a diamine can be used to form a tetraurea:
  • a diisocyanate, an alcohol and a diamine can be used to form a triurea-urethane:
  • Urea greases are formed by carrying out these reactions in a base oil, thereby directly providing the grease product wherein the urea thickener is dispersed throughout the base oil.
  • the reaction of the diisocyanate and the amine does not require any heat and proceeds at a good rate at room temperature. There are no reaction byproducts that must be removed.
  • the diisocyanate reagents are highly toxic and volatile and require special treatment and handling equipment. It is desirable to find an alternative route for the manufacture of urea greases that avoids the use of diisocyanate reagents.
  • the invention provides a process for preparing a urea grease comprising one or more steps in which a compound of formula (I), a compound of formula (II) and a compound of formula (III) are reacted: (I) (II) (III) wherein R 1 and R 2 are chosen from hydrocarbyl having from 1 to 30 carbon atoms, or R 1 and R 2 are linked and form a hydrocarbylene group having from 1 to 30 carbon atoms, R 3 is chosen from hydrocarbyl comprising from 2 to 30 carbon atoms and R 4 is hydrocarbylene comprising from 2 to 30 carbon atoms; wherein at least one of the reaction steps is carried out in the presence of a base oil.
  • urea grease may be prepared by reacting compounds (I), (II) and (III) wherein at least one of the reaction steps takes place in the presence of a base oil.
  • hydrocarbyl refers to a monovalent organic radical comprising hydrogen and carbon and may be aliphatic, aromatic or alicyclic, for example, but not limited to, aralkyl, alkyl, aryl, cycloalkyl, alkylcycloalkyl, or a combination thereof, and may be saturated or olefinically unsaturated (one or more double-bonded carbons, conjugated or non-conjugated).
  • hydrocarbylene refers to a divalent organic radical comprising hydrogen and carbon and may be aliphatic, aromatic or alicyclic, for example, but not limited to, aralkyl, alkyl, aryl, cycloalkyl or alkylcycloalkyl, and may be saturated or olefinically unsaturated (one or more double-bonded carbons, conjugated or non-conjugated).
  • the invention provides a process for the preparation of a urea grease.
  • a compound of formula (I), a compound of formula (II) and a compound of formula (III) are reacted:
  • R 1 and R 2 are chosen from hydrocarbyl having from 1 to 30 carbon atoms, or R 1 and R 2 are linked and form a hydrocarbylene group having from 1 to 30 carbon atoms.
  • R 1 and R 2 are preferably hydrocarbyl groups or a hydrocarbylene group comprising only hydrogen and carbon atoms, but it is possible that R 1 and R 2 may also comprise heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents, particularly if one or more of R 1 or R 2 is an aryl group.
  • R 1 and R 2 are chosen from aryl having from 6 to 12 carbon atoms and alkyl having from 1 to 12 carbon atoms, or R 1 and R 2 are linked and form an alkylene group having from 1 to 12 carbon atoms.
  • R 1 and R 2 are chosen from phenyl and substituted-phenyl groups having from 6 to 12 carbon atoms and alkyl groups having from 1 to 12 carbon atoms, or R 1 and R 2 are linked and form an alkylene group having from 1 to 6 carbon atoms.
  • Substituted phenyl includes methyl-substituted or ethyl-substituted phenyl (preferably in the para or ortho positions) or ethoxy-substituted phenyl.
  • R 1 and R 2 are both phenyl or R 1 and R 2 are linked and form an ethylene group, i.e. the compound of formula (I) is diphenylene carbonate or ethylene carbonate.
  • R 1 and R 2 are suitably chosen such that R 1- OH and R 2 -OH (or HO-R 1 -R 2 -OH) are compounds that may be readily removed from the reaction mixture.
  • R 3 is chosen from hydrocarbyl comprising from 2 to 30 carbon atoms.
  • R 3 preferably comprises only hydrogen and carbon atoms, but it is possible that R 3 may also comprise heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents, particularly if R 3 is an aryl group.
  • R 3 is aryl having from 6 to 12 carbon atoms or is alkyl comprising from 2 to 18 carbon atoms.
  • the compound of formula (II) is chosen from octylamine, dodecylamine (laurylamine), tetradecylamine (myristylamine), hexadecylamine, octadecylamine (tallow amine, also referred to as stearylamine), oleylamine, aniline, benzyl amine, p-toluidine, p-chloro-aniline or m-xylidine.
  • R 4 is hydrocarbylene comprising from 2 to 30 carbon atoms.
  • R 4 preferably comprises only hydrogen and carbon atoms, but it is possible that R 4 may also comprise heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents particularly if R 4 is an arylene group.
  • R 4 is arylene comprising from 6 to 12 carbon atoms or alkylene comprising from 2 to 12 carbon atoms.
  • the compound of formula (III) is chosen from arylene comprising from 6 to 12 carbon atoms. Preferred compounds of formula (III) are shown below:
  • a compound of formula (I), a compound of formula (II) and a compound of formula (III) are reacted in one step in the presence of a base oil.
  • the reaction takes place in two steps and the second step takes place in the presence of a base oil.
  • the process for preparing a urea grease comprises steps of:
  • step (a1) the compound of formula (I) reacts with the compound of formula (II):
  • step (a1) If R 1 and R 2 are linked and form a hydrocarbylene group, then there will be just one product. If R 1 and R 2 are hydrocarbyl groups (and are not linked), then an alcohol byproduct will result in step (a1) and this byproduct is preferably removed before step (b1).
  • a diurea grease is suitably prepared by reacting compounds of formula (I) and (II) in step (a1) and subsequently reacting the product of step (a1) with a compound of formula (III) in step (b1):
  • step (a1) the compounds of formula (I) and (II) are additionally reacted with a compound of formula (IV): H 2 N-R 5 -NH 2 (IV) wherein R 5 is hydrocarbylene comprising from 2 to 30 carbon atoms.
  • step (a1) is then reacted with a compound of formula (III) in step (b1):
  • R 5 preferably comprises only hydrogen and carbon atoms, but it is possible that R 5 may also comprise heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents.
  • R 5 is preferably arylene comprising from 6 to 12 carbon atoms or alkylene comprising from 2 to 12 carbon atoms.
  • Preferred compounds of formula (IV) include ethylenediamine, propylenediamine, butylenediamine, pentylenediamine and hexamethylenediamine.
  • step (a1) the compounds of formula (I) and (II) are additionally reacted with a compound of formula (V) and a compound of formula (VI): R 6 OH (V) H 2 N-R 7 -NH 2 (VI) wherein R 6 and R 7 are independently chosen from hydrocarbyl comprising from 2 to 30 carbon atoms.
  • step (a1) The product of step (a1) is then reacted with a compound of formula (III) in step (b1):
  • R 6 preferably comprises only hydrogen and carbon atoms, but it is possible that R 6 may also comprise heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents.
  • R 6 is preferably alkylene or alkenylene comprising from 2 to 24 carbon atoms.
  • Preferred compounds of formula (V) include 1-dodecanol (lauryl alcohol), 1-tetradecanol (myristyl alcohol), 1-hexadecanol (cetyl (or palmityl) alcohol), 1-octadecanol (stearyl alcohol), cis-9-octadecen-1-ol (oleyl alcohol), 9-octadecadien-1-ol (unsaturated palmitoleyl alcohol), 12-octadecadien-1-ol (linoleyl alcohol).
  • R 7 preferably comprises only hydrogen and carbon atoms, but it is possible that R 7 may also comprise heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents.
  • R 7 preferably arylene comprising from 6 to 12 carbon atoms or alkylene comprising from 2 to 12 carbon atoms.
  • Preferred compounds of formula (VI) include ethylenediamine, propylenediamine, butylenediamine, pentylenediamine and hexamethylenediamine.
  • step (b1) Before the product of step (a1) is used in step (b1) it is preferable to remove any unreacted compounds of formula (I) and (II), any solvent that may have been used and any byproducts (especially R 1 -OH and R 2 -OH compounds). Removal is suitably achieved using vacuum.
  • step (a2) the compound of formula (I) reacts with the compound of formula (III):
  • step (a2) If R 1 and R 2 are linked and form a hydrocarbylene group, then there will be just one product. If R 1 and R 2 are hydrocarbyl groups (and are not linked), then an alcohol byproduct will result in step (a2) and this byproduct is preferably removed before step (b2).
  • a diurea grease is suitably prepared by reacting compounds of formula (I) and (III) in step (a2) and subsequently reacting the product of step (a2) with a compound of formula (II) in step (b2) in the presence of a base oil:
  • step (a2) the compounds of formula (I) and (III) are additionally reacted with a compound of formula (IV): H 2 N-R 5 - NH 2 (IV) wherein R 5 is hydrocarbylene comprising from 2 to 30 carbon atoms.
  • R 5 is hydrocarbylene comprising from 2 to 30 carbon atoms.
  • Preferred R 5 groups are as described for the first preferred embodiment of the invention.
  • step (a2) the compound of formula (I) will react with the compound of formula (III), and the compound of formula (I) will react with the compound of formula (IV).
  • step (b2) the reaction products of step (a2) are then reacted with a compound of formula (II):
  • step (a2) the compounds of formula (I) and (III) are additionally reacted with compounds of formula (V) and (VI): R 6 -OH H 2 N-R 7 - NH 2 (V) (VI) wherein R 6 and R 7 are independently chosen from hydrocarbyl comprising from 2 to 30 carbon atoms. Preferred R 6 and R 7 groups are as described for the first embodiment of the invention.
  • step (a2) the compound of formula (I) will react with the compound of formula (III), the compound of formula (I) will react with the compound of formula (V) and the compound of formula (I) will react with the compound of formula (VI).
  • step (b2) the reaction products of step (a2) are then reacted with a compound of formula (II):
  • step (b2) Before the product(s) of step (a2) is/are used in step (b2) it is preferable to remove any unreacted compounds of formula (I) and (III), any solvent that may have been used and any byproducts (especially R 1 -OH and R 2 -OH compounds). Removal is suitably achieved using vacuum or adequate solvent washes.
  • step (a1) and (a2) The preferred reaction conditions in step (a1) and (a2) will be affected by the choice of the compound (I). If compound (I) is diphenyl carbonate, then step (a1) or (a2) preferably takes place without solvent or in the presence of a solvent such as toluene or dimethylformamide. The reaction preferably takes place in the presence of a catalyst such as diphenylphosphinic acid. Phenol will be produced as a byproduct of the reaction. The phenol byproduct should be removed, e.g. by use of a vacuum.
  • compound (I) is dimethyl carbonate
  • a catalyst such as dibutyl tin methoxide, dibutyl tin dilaurate or tin (II) octoate.
  • Other catalysts that could be used include potassium t-butoxide, copper (II) acetylacetonate, DABCO BL11 and DABCO LV33.
  • step (b1) and (b2) will be affected by the choice of the compound (I). If compound (I) is diphenyl carbonate then the reactants are preferably heated to at least 90°C and more preferably about 100°C. The reaction is preferably carried out in the absence of catalyst. If compound (I) is dimethyl carbonate then the reactants are preferably heated to at least 130°C and more preferably about 140°C. The reaction is preferably carried out in the presence of a catalyst such as dibutyl tin dilaurate. The inventors have found that additional heating is often necessary to transform the reaction product of step (b1) or (b2) into a grease. Preferably the reaction products of step (b1) or (b2) are heated to at least 170°C and then cooled.
  • a catalyst such as dibutyl tin dilaurate
  • the base oil that is present in at least one of the reaction steps may be of mineral origin, synthetic origin, or a combination thereof.
  • Base oils of mineral origin may be mineral oils, for example, those produced by solvent refining or hydroprocessing.
  • Base oils of synthetic origin may typically comprise mixtures of C 10 -C 50 hydrocarbon polymers, for example, polymers of alphaolefins, ester type synthetic oils, ether type synthetic oils, and combinations thereof.
  • Base oils may also include Fischer-Tropsch derived highly paraffinic products.
  • mineral base oils include paraffinic base oils and naphthenic base oils.
  • Paraffinic base oils typically have a proportion of carbons in aromatic structure (Ca) in a range of from 1 to 10%, in naphthenic structure (Cn) in a range of from 20 to 30% and in paraffinic structure (Cp) in a range of from 60 to 70%.
  • Naphthenic base oils typically have a proportion of carbons in aromatic structure (Ca) in a range of from 1 to 20%, in naphthenic structure (Cn) in a range of from 30 to 50% and in paraffinic structure (Cp) in a range of from 40 to 60%.
  • Suitable examples of base oils include medium viscosity mineral oils, high viscosity mineral oils, and combinations thereof.
  • Medium viscosity mineral oils have a viscosity generally in a range of from 5 mm 2 /s centistokes (cSt) at 100 °C to 15 mm 2 /s (cSt) at 100 °C, preferably in a range of from 6 mm 2 /s (cSt) at 100 °C to 12 mm 2 /s (cSt) at 100 °C, and more preferably in a range of from 7 mm 2 /s (cSt) at 100 °C to 12 mm 2 /s (cSt) at 100 °C.
  • High viscosity mineral oils have a viscosity generally in a range of from 15 mm 2 /s (cSt) at 100 °C to 40 mm 2 /s (cSt) at 100 °C and preferably in a range of from 15 mm 2 /s (cSt) at 100 °C to 30 mm 2 /s (cSt) at 100 °C.
  • mineral oils that may conveniently be used include those sold by member companies of the Shell Group under the designations "HVI”, “MVIN”, or “HMVIP”.
  • Polyalphaolefins and base oils of the type prepared by the hydroisomerisation of wax for example, those sold by member companies of the Shell Group under the designation "XHVI” (trade mark), may also be used.
  • the urea grease that is the product of the process of the invention comprises a urea thickener and a base oil.
  • the urea grease comprises a weight percent of urea based on the total weight of urea grease in a range of from 2 weight percent to 25 weight percent, more preferably in a range of from 3 weight percent to 20 weight percent, and most preferably in a range of from 5 weight percent to 20 weight percent.
  • the product of the process of the invention is a urea grease.
  • the base grease that results from step (b1) or step (b2) is subjected to further finishing procedures such as homogenisation, filtration and deaeration.
  • a urea grease prepared according to a process of the invention may comprise one or more additives, in amounts normally used in this field of application, to impart certain desirable characteristics to the urea grease including, for example, oxidation stability, tackiness, extreme pressure properties, corrosion inhibition, reduced friction and wear, and combinations thereof.
  • the additives are preferably added to the base grease before the finishing procedures. Most preferably, the base grease is homogenised, then the additives are added, and then the grease is subjected to further homogenization.
  • a urea grease prepared according to a process of the invention may comprise from 0.1 weight percent to 15 weight percent, preferably from 0.1 weight percent to 5 weight percent, more preferably from 0.1 weight percent to 2 weight percent, and even more preferably from 0.2 weight percent to 1 weight percent of one or more additives based on the total weight of urea grease.
  • urea greases produced by the process of the invention are suitably used in typical applications for urea greases such as in constant-velocity joints, ball joints, wheel bearings, alternators, cooling fans, ball screws, linear guides of machine tools, sliding areas of construction equipment, and bearings and gears in steel equipment and various other industrial mechanical facilities.
  • a urea grease may be prepared by a process comprising one or more steps in which a compound of formula (I), a compound of formula (II) and a compound of formula (III) are reacted: wherein R 1 and R 2 are chosen from hydrocarbyl having from 1 to 30 carbon atoms, or R 1 and R 2 are linked and form a hydrocarbylene group having from 1 to 30 carbon atoms, R 3 is chosen from hydrocarbyl comprising from 2 to 30 carbon atoms and R 4 is hydrocarbylene comprising from 2 to 30 carbon atoms; and comprising a step wherein the resulting urea product is dispersed in a base oil.
  • the urea is synthesised from compounds (I), (II) and (III) and then the urea powder is dispersed in a base oil to form a grease.
  • Figure 1 shows a process wherein diphenyl-carbonate (2) is reacted with ethylenediamine (4) and octylamine (1) without solvent under nitrogen atmosphere. After the reaction is completed the excess phenol is removed in vacuum. The two intermediates (3,5) are then combined to the final tetraurea (7) by introducing the methylene diphenyl diamine (6) under the same conditions and in the presence of a base oil. The reaction product is heated to 170°C to form a tetraurea grease.
  • Figure 2 shows a process wherein octylamine (1) and ethylenediamine (4) are added to a ice-cooled solution of ethylenecarbonate (8) in water.
  • the reaction is catalysed with (Bu 2 Sn(OMe) 2 ).
  • the solvent and excess amines are removed under vacuum and the products 9 and 10 are isolated.
  • the products 9 and 10 and the methylene diphenyl diamine (6) are connected at 150°C catalysed by (Bu 2 Sn(OMe) 2 ) and the presence of a base oil.
  • the resulting ethylene glycol is removed in vacuum.
  • the reaction product is heated to 170°C to form a tetraurea grease.
  • Figure 3 shows a process wherein dimethylcarbonate (1) and 4,4'-methylenedianiline (2) are reacted at 80°C in the presence of potassium t-butoxide. Methanol will be removed as a byproduct.
  • the diphenylcarbamate product (3) is reacted with octylamine (4) in the presence of a base oil and dibutyltin dilaureate at 100°C to provide a grease product which is a diurea in base oil.
  • the reaction product is heated to 170°C to form a diurea grease.
  • Figure 4 shows a process wherein diphenylcarbonate (1) and 4,4'-methylenedianiline (2) are reacted at 100°C in the presence of diphenylphosphinic acid. Phenol will be removed as a byproduct.
  • the diphenylcarbamate product (3) is reacted with octylamine (4) in the presence of a base oil at 100°C to provide a grease product which is a diurea in base oil.
  • the reaction product is heated to 170°C to form a diurea grease.
  • the product was worked up by adding dimethyl ether, filtering and washing with dimethyl ether. A yield of 91-94% diphenylcarbamate was achieved.
  • 4,4'-methylenedianiline was heated with potassium t-butoxide (4.4 eq) in dimethyl carbonate (neat) at 80°C for 0.5h to give dimethylcarbamate (89%) after filtration and washing with water.
  • Dimethylcarbamate (65g) prepared according to example 3a was reacted with octylamine and dibutyltin dilaureate (added over several days) in base oil at 140°C for 7 days to give the diurea product together with some mono-urea. 498g of a grease was isolated. The properties of the grease were measured and are shown in Table 1.
  • the delta penetration is as low as possible, and low values were achieved by some of the greases.
  • the worked penetration values range from 247 to 340 which will give greases that would typically fall into the category of NLGI grade 1, 2 or 3.
  • the dropping point is desirably as high as possible and several of the greases gave dropping points in excess of 300.

Claims (8)

  1. Procédé de préparation d'une graisse à base d'urée comprenant une ou plusieurs étapes dans lesquelles on fait réagir un composé de formule (I), un composé de formule (II) et un composé de formule (III) :
    Figure imgb0040
     dans lesquelles R1 et R2 sont choisis parmi les groupes hydrocarbyle ayant de 1 à 30 atomes de carbone, ou bien R1 et R2 sont liés et forment un groupe hydrocarbylène ayant de 1 à 30 atomes de carbone, R3 est choisi parmi les groupes hydrocarbyle comprenant de 2 à 30 atomes de carbone et R4 est un groupe hydrocarbylène comprenant de 2 à 30 atomes de carbone ;
    au moins une des étapes réactionnelles étant réalisée en présence d'une huile de base.
  2. Procédé de préparation d'une graisse à base d'urée selon la revendication 1, comprenant les étapes consistant à :
    (a1) faire réagir un composé de formule (I) avec un composé de formule (II)
    Figure imgb0041
     et
    (b1) faire réagir le produit de l'étape (a1) avec un composé de formule (III) :

            H2N-R4 -NH2      (III)

    dans lequel l'étape (b1) est réalisée en présence d'une huile de base.
  3. Procédé de préparation d'une graisse à base d'urée selon la revendication 1 comprenant les étapes consistant à :
    (a2) faire réagir un composé de formule (I) avec un composé de formule (III)
    Figure imgb0042
     et
    (b2) faire réagir le produit de l'étape (a2) avec un composé de formule (II) :

            R3- NH2      (II)

    dans lequel l'étape (b2) est réalisée en présence d'une huile de base.
  4. Procédé selon la revendication 2 ou la revendication 3, dans lequel un catalyseur est présent à l'étape (a1), l'étape (a2), l'étape (b1) et/ou l'étape (b2).
  5. Procédé selon la revendication 2, 3 ou 4 dans lequel les produits réactionnels de l'étape (b1) ou (b2) sont chauffés jusqu'à au moins 170 °C puis refroidis.
  6. Procédé selon une quelconque revendication précédente, dans lequel la graisse à base d'urée comprend un pourcentage pondéral d'urée rapporté au poids total de la graisse à base d'urée dans une gamme de 2 pour cent en poids à 25 pour cent en poids.
  7. Procédé selon une quelconque revendication précédente, dans lequel la graisse est soumise à une ou plusieurs procédures de finition choisies parmi l'homogénéisation, la filtration et la désaération.
  8. Procédé selon une quelconque revendication précédente, dans lequel un ou plusieurs additifs sont ajoutés à la graisse.
EP14703097.7A 2013-02-08 2014-02-07 Procédé de préparation de graisse à base d'urée Active EP2954035B1 (fr)

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EP14703097.7A EP2954035B1 (fr) 2013-02-08 2014-02-07 Procédé de préparation de graisse à base d'urée

Applications Claiming Priority (3)

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EP13154677 2013-02-08
EP14703097.7A EP2954035B1 (fr) 2013-02-08 2014-02-07 Procédé de préparation de graisse à base d'urée
PCT/EP2014/052454 WO2014122273A1 (fr) 2013-02-08 2014-02-07 Procédé de préparation d'une graisse à base d'urée

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EP (1) EP2954035B1 (fr)
JP (1) JP6211100B2 (fr)
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BR (1) BR112015017754A2 (fr)
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WO2018092806A1 (fr) * 2016-11-16 2018-05-24 出光興産株式会社 Composition de graisse pour équipement doté d'un dispositif d'alimentation en graisse automatique, et procédé de production associé
JPWO2020218522A1 (fr) * 2019-04-26 2020-10-29
JP7382250B2 (ja) 2020-02-14 2023-11-16 株式会社ネオス ポリウレアポリウレア化合物とこれを含む組成物ならびにポリウレア硬化物、およびポリウレア硬化物を含む成形フィルムならびに成形品
WO2022019198A1 (fr) * 2020-07-22 2022-01-27 株式会社ジェイテクト Matière première pour graisse, procédé de production de matière première de graisse, procédé de production de graisse et graisse

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Publication number Publication date
RU2015138152A (ru) 2017-03-16
CN104981536A (zh) 2015-10-14
WO2014122273A1 (fr) 2014-08-14
JP2016506985A (ja) 2016-03-07
US20160002557A1 (en) 2016-01-07
EP2954035A1 (fr) 2015-12-16
JP6211100B2 (ja) 2017-10-11
BR112015017754A2 (pt) 2017-07-11
RU2646606C2 (ru) 2018-03-06

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