WO2014122273A1 - Process for preparing a urea grease - Google Patents
Process for preparing a urea grease Download PDFInfo
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- WO2014122273A1 WO2014122273A1 PCT/EP2014/052454 EP2014052454W WO2014122273A1 WO 2014122273 A1 WO2014122273 A1 WO 2014122273A1 EP 2014052454 W EP2014052454 W EP 2014052454W WO 2014122273 A1 WO2014122273 A1 WO 2014122273A1
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- WO
- WIPO (PCT)
- Prior art keywords
- formula
- compound
- grease
- carbon atoms
- urea
- Prior art date
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- 0 CN(C(*)=O)*(N(*)C(*)=O)=C Chemical compound CN(C(*)=O)*(N(*)C(*)=O)=C 0.000 description 1
Classifications
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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
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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
- 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
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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
- 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
- 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:
- 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;
- reaction steps wherein at least one of the reaction steps is carried out in the presence of a base oil.
- the process of the invention provides a urea grease, but avoids the use of diisocyanate reagents.
- Isocyanate-free syntheses of ureas are described by Luc Ubaghs in the PhD thesis "Isocyanate-free synthesis of (functional) polyureas, polyurethanes and urethane-containing
- urea greases 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.
- FIG. 1 is a reaction scheme showing the
- FIG. 4 is a reaction scheme showing the
- 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,
- 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 may be saturated or olefinically unsaturated (one or more double-bonded carbons,
- 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
- 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
- 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
- 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 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 Pre ow:
- 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 (bl) reacting the product of step (al) with a compound of formula ( III ) :
- step (bl) is carried out in the presence of a base oil.
- the process for preparing a urea grease comprises steps of:
- step (b2) reacting the product of step (a2) with a compound of formula (II) :
- step (b2) is carried out in the presence of a base oil.
- step (al) the compound of formula (I) reacts with the compound of formula ( II ) :
- 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 (al) and this byproduct is preferably removed before step (bl) .
- a diurea grease is suitably prepared by reacting compounds of formula (I) and (II) in step (al) and subsequently reacting the product of step (al) with a compound of formula (III) in step (bl) :
- step (al) the compounds of formula (I) and (II) are additionally reacted with a compound of formula (IV) :
- step (al) wherein R 5 is hydrocarbylene comprising from 2 to 30 carbon atoms.
- step (al) is then reacted with a compound of formula (III) in step (bl) :
- 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,
- step (al) the compounds of formula (I) and (II) are additionally reacted with a compound of formula (V) and a compound of formula (VI) :
- R 6 and R 7 are independently chosen from
- step (al) hydrocarbyl comprising from 2 to 30 carbon atoms.
- step (al) hydrocarbyl comprising from 2 to 30 carbon atoms.
- step (bl) hydrocarbyl comprising from 2 to 30 carbon atoms.
- 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-l-ol (oleyl alcohol), 9-octadecadien-l-ol (unsaturated palmitoleyl alcohol), 12-octadecadien-l-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,
- step (bl) Before the product of step (al) is used in step (bl) 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
- Removal is suitably achieved using vacuum.
- step (a2) the compound of formula (I) reacts with the compound of formula ( III ) :
- step (I) 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) :
- 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) :
- hydrocarbyl comprising from 2 to 30 carbon atoms.
- 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 -0H and R 2 -0H compounds). Removal is suitably achieved using vacuum or adequate solvent washes .
- step (al) and (a2) will be affected by the choice of the compound (I) . If compound (I) is diphenyl carbonate, then step (al) or (a2) preferably takes place without solvent or in the presence of a solvent such as toluene or
- 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.
- 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 BLll and DABCO LV33.
- step (bl) and (b2) will be affected by the choice of the compound (I) .
- 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.
- 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.
- a catalyst such as dibutyl tin dilaurate.
- the inventors have found that additional heating is often necessary to transform the reaction product of step (bl) or (b2) into a grease.
- the reaction products of step (bl) or (b2) are heated to at least 170°C and then cooled.
- 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 ]_ Q -
- C50 hydrocarbon polymers for example, polymers of alpha- olefins, 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
- 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
- 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 (bl) or step (b2) is subjected to further finishing procedures such as homogenisation, filtration and de- aeration .
- 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 .
- salicylates or alkylarylsulphonates ; one or more ashless dispersant additives, such as reaction products of polyisobutenyl succinic anhydride and an amine or ester; one or more antioxidants, such as hindered phenols or amines, for example phenyl alpha naphthylamine,
- diphenylamine or alkylated diphenylamine ; one or more antirust additives such as oxygenated hydrocarbons which have optionally been neutralised with calcium, calcium salts of alkylated benzene sulphonates and alkylated benzene petroleum sulphonates, and succinic acid
- Solid materials such as graphite, finely divided MoS 2 , talc, metal powders, and various polymers such as polyethylene wax may also be added to impart special properties .
- 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:
- 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;
- 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 than 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
- 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 .
- FIG. 4 shows a process wherein diphenylcarbonate
- Example Id Step (b2) - Synthesis of Diurea in Base Oil lOlg of diphenylcarbamate, prepared according to Example la, was heated in base oil (506g) and octylamine (60g) overnight at 96 °C. The mixture was cooled and stirred with acetone (4x500ml), settled and decanted to remove phenol and by-products (according to NMR 95% pure) . The material was dried using a rotary evaporator and heated to 170°C then cooled down to form a grease. The properties of the grease were measured and are shown in Table 1.
- Example 2 One-Pot Two-Step Synthesis of Diurea in Base Oil
- the dicarbamate was reacted with octylamine for 2 hrs at 105 °C.
- the product was washed with dichloromethane and was then purified by crystallization from
- 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.
Abstract
Description
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Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015556509A JP6211100B2 (en) | 2013-02-08 | 2014-02-07 | Urea grease manufacturing method |
EP14703097.7A EP2954035B1 (en) | 2013-02-08 | 2014-02-07 | Process for preparing a urea grease |
BR112015017754A BR112015017754A2 (en) | 2013-02-08 | 2014-02-07 | process for preparing a urea lubricant |
US14/765,946 US20160002557A1 (en) | 2013-02-08 | 2014-02-07 | Process for preparing a urea grease |
RU2015138152A RU2646606C2 (en) | 2013-02-08 | 2014-02-07 | Process for preparing a urea grease |
CN201480007940.1A CN104981536A (en) | 2013-02-08 | 2014-02-07 | Process for preparing urea grease |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP13154677 | 2013-02-08 | ||
EP13154677.2 | 2013-02-08 |
Publications (1)
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WO2014122273A1 true WO2014122273A1 (en) | 2014-08-14 |
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PCT/EP2014/052454 WO2014122273A1 (en) | 2013-02-08 | 2014-02-07 | Process for preparing a urea grease |
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US (1) | US20160002557A1 (en) |
EP (1) | EP2954035B1 (en) |
JP (1) | JP6211100B2 (en) |
CN (1) | CN104981536A (en) |
BR (1) | BR112015017754A2 (en) |
RU (1) | RU2646606C2 (en) |
WO (1) | WO2014122273A1 (en) |
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WO2018092806A1 (en) * | 2016-11-16 | 2018-05-24 | 出光興産株式会社 | Grease composition for equipment provided with automatic grease feeder, and production method therefor |
CN113677782A (en) * | 2019-04-26 | 2021-11-19 | 引能仕株式会社 | Lubricating oil composition |
JP7382250B2 (en) | 2020-02-14 | 2023-11-16 | 株式会社ネオス | Polyurea Polyurea compounds, compositions containing the same, cured polyurea products, and molded films and molded products containing the cured polyurea products |
JPWO2022019198A1 (en) * | 2020-07-22 | 2022-01-27 |
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- 2014-02-07 RU RU2015138152A patent/RU2646606C2/en active
- 2014-02-07 JP JP2015556509A patent/JP6211100B2/en active Active
- 2014-02-07 BR BR112015017754A patent/BR112015017754A2/en not_active Application Discontinuation
- 2014-02-07 CN CN201480007940.1A patent/CN104981536A/en active Pending
- 2014-02-07 US US14/765,946 patent/US20160002557A1/en not_active Abandoned
- 2014-02-07 WO PCT/EP2014/052454 patent/WO2014122273A1/en active Application Filing
- 2014-02-07 EP EP14703097.7A patent/EP2954035B1/en active Active
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Also Published As
Publication number | Publication date |
---|---|
RU2646606C2 (en) | 2018-03-06 |
RU2015138152A (en) | 2017-03-16 |
CN104981536A (en) | 2015-10-14 |
EP2954035A1 (en) | 2015-12-16 |
BR112015017754A2 (en) | 2017-07-11 |
US20160002557A1 (en) | 2016-01-07 |
JP6211100B2 (en) | 2017-10-11 |
EP2954035B1 (en) | 2016-12-21 |
JP2016506985A (en) | 2016-03-07 |
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