JP6211100B2 - Urea grease manufacturing method - Google Patents

Description

  The present invention relates to a method for producing urea grease.

  Urea greases are constant velocity joints, ball joints, wheel bearings, alternators, cooling fans, ball screws, machine tool linear guides, bearings for construction equipment sliding areas, as well as steel equipment and various other industrial Used in various applications such as bearings and gears in machinery facilities. Urea grease typically has excellent heat and oxidation resistance and can extend the life of the bearing.

  Urea grease contains a low molecular weight organic compound, and this compound is sometimes referred to as polyurea usually synthesized from isocyanate and amine. Diisocyanates and monoamines can be used to form diureas:

  Diisocyanates and diamines can be used to form tetraureas:

  Diisocyanates, alcohols and diamines can be used to form triureaurethanes:

  Urea greases are formed by performing these reactions in a base oil and feeding grease products directly, where a urea thickener is dispersed throughout the base oil.

  The reaction between the diisocyanate and the amine requires no heat and proceeds at an excellent rate at room temperature. There are no reaction by-products that need to be removed. However, diisocyanate reagents are highly toxic and volatile and require special processing and handling equipment. In order to avoid the use of diisocyanate reagents, it is desirable to find alternative routes for urea grease production.

  Accordingly, the present invention is a process for producing urea grease, which comprises a compound of formula (I), a compound of formula (II) and a compound of formula (III):

Wherein R ¹ and R ² are selected from hydrocarbyl having 1 to 30 carbon atoms, or R ¹ and R ² are linked to hydrocarbylene having 1 to 30 carbon atoms. One or more reacting, wherein R ³ is selected from hydrocarbyl containing 2 to 30 carbon atoms and R ⁴ is hydrocarbylene containing 2 to 30 carbon atoms) The method is provided comprising a number of steps, wherein at least one of the reaction steps is carried out in the presence of a base oil.

  The method of the present invention provides urea grease, but avoids the use of diisocyanate reagents. Isocyanate-free urea synthesis is a Luc Ubaghs PhD thesis, “Isocyanate-free synthesis of (functional) polyureas, polyurethanes and urethane-containing copolymers. This document does not disclose the production of urea grease. The inventors have found that urea grease can be produced by reacting compounds (I), (II) and (III) where at least one of the reaction steps takes place in the presence of a base oil. .

FIG. 1 is a reaction scheme showing the production of urea grease according to the present invention. FIG. 2 is a reaction scheme showing the production of urea grease according to the present invention. FIG. 3 is a reaction scheme showing the production of urea grease according to the present invention. FIG. 4 is a reaction scheme showing the production of urea grease according to the present invention.

  The term “hydrocarbyl” as used in the description of the present invention refers to a monovalent organic radical comprising hydrogen and carbon and may be aliphatic, aromatic or alicyclic, such as, but not limited to, May be aralkyl, alkyl, aryl, cycloalkyl, alkylcycloalkyl, or combinations thereof, and may be saturated or olefinically unsaturated (one or more divalents). They may have carbons that are heavily bonded, may be conjugated, or may not be conjugated). The term “hydrocarbylene” as used in the description of the present invention refers to a divalent organic radical comprising hydrogen and carbon, which may be aliphatic, aromatic or alicyclic, such as these Without limitation, it may be aralkyl, alkyl, aryl, cycloalkyl or alkylcycloalkyl and may be saturated or olefinically unsaturated (one or more double bonded It may have carbon, may be conjugated, or may not be conjugated).

  The present invention provides a method for producing urea grease. The compound of formula (I), the compound of formula (II) and the compound of formula (III) are reacted:

R ¹ and R ² are selected from hydrocarbyl having 1 to 30 carbon atoms, or R ¹ and R ² are linked to form a hydrocarbylene group having 1 to 30 carbon atoms To do. R ¹ and R ² are preferably hydrocarbyl or hydrocarbylene groups containing only hydrogen and carbon atoms, but particularly when one or both of R ¹ or R ² is an aryl group, R ¹ and R 2 ^It is also contemplated that 2 may also contain heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents. Suitably R ¹ and R ² are selected from aryl having 6-12 carbon atoms and alkyl having 1-12 carbon atoms, or R ¹ and R ² are linked, An alkylene group having 1 to 12 carbon atoms is formed. Preferably, R ¹ and R ² are selected from phenyl and substituted phenyl groups having 6-12 carbon atoms, and alkyl groups having 1-12 carbon atoms, or R ¹ and R ² are To form an alkylene group having 1 to 6 carbon atoms. Substituted phenyl includes methyl substituted or ethyl substituted phenyl (preferably in the para or ortho position) or ethoxy substituted phenyl. Most preferably, R ¹ and R ² are both phenyl or R ¹ and R ² are linked to form an ethylene group, ie the compound of formula (I) is diphenylene carbonate or ethylene Carbonate. R ¹ and R ² are preferably selected such that R ¹ —OH and R ² —OH (or HO—R ¹ —R ² —OH) can be easily removed from the reaction mixture.

R ³ is selected from hydrocarbyl containing 2 to 30 carbon atoms. R ³ preferably includes only hydrogen and carbon atoms, but particularly when R ³ is an aryl group, R ³ also includes heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents. It may be possible. Preferably R ³ is aryl having 6 to 12 carbon atoms or alkyl containing 2 to 18 carbon atoms. Most preferably, the compound of formula (II) is also referred to as octylamine, dodecylamine (laurylamine), tetradecylamine (myristylamine), hexadecylamine, octadecylamine (tallow amine, also stearylamine). ), Oleylamine, aniline, benzylamine, p-toluidine, p-chloro-aniline or m-xylidine.

R ⁴ is a hydrocarbylene containing 2 to 30 carbon atoms. R ⁴ preferably contains only hydrogen and carbon atoms, but particularly when R ⁴ is an arylene group, R ⁴ also contains a heteroatom substituent such as a halo, nitro, hydroxyl or alkoxy substituent. It may be possible. Preferably R ⁴ is arylene containing 6 to 12 carbon atoms or alkylene containing 2 to 12 carbon atoms. Most preferably, the compound of formula (III) is selected from arylene containing 6 to 12 carbon atoms. Preferred compounds of formula (III) are shown below:

In one embodiment of the method of the invention, the compound of formula (I), the compound of formula (II) and the compound of formula (III) are reacted in one step in the presence of a base oil. However, in a more preferred embodiment, the reaction is performed in two steps and the second step is performed in the presence of a base oil. In a first preferred embodiment, the method for producing urea grease comprises:
(A1) reacting a compound of formula (I) with a compound of formula (II): and

(B1) reacting the product of step (a1) with a compound of formula (III):

Wherein step (b1) is carried out in the presence of a base oil. In a second preferred embodiment, the method for producing urea grease comprises:
(A2) reacting a compound of formula (I) with a compound of formula (III): and

(B2) reacting the product of step (a2) with a compound of formula (II):

Wherein step (b2) is carried out in the presence of a base oil.

  In a first preferred embodiment, in step (a1), the compound of formula (I) is reacted with a compound of formula (II):

When R ¹ and R ² are linked to form a hydrocarbylene group, only one product is expected. If R ¹ and R ² are hydrocarbyl groups (and are not linked), an alcohol by-product is expected to occur in step (a1), and this by-product is preferably removed prior to step (b1).

  The diurea grease preferably reacts the compounds of formula (I) and (II) in step (a1) and then reacts the product of step (a1) with the compound of formula (III) in step (b1) Manufactured by:

  When tetraurea grease is the desired product, in step (a1), the compounds of formula (I) and (II) are converted to compounds of formula (IV):

(Wherein R ⁵ is a hydrocarbylene containing 2 to 30 carbon atoms). Then in step (b1) the product of step (a1) is reacted with a compound of formula (III):

R ⁵ preferably contains only hydrogen and carbon atoms, although it is believed that R ⁵ may also contain heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents. R ⁵ is preferably arylene containing 6 to 12 carbon atoms or alkylene containing 2 to 12 carbon atoms. Preferred compounds of formula (IV) include ethylene diamine, propylene diamine, butylene diamine, pentylene diamine and hexamethylene diamine.

  When triurea urethane grease is the desired product, in step (a1), the compound of formula (I) and (II) is replaced with a compound of formula (V) and a compound of formula (VI);

Further reaction with (wherein R ⁶ and R ⁷ are independently selected from hydrocarbyl containing 2 to 30 carbon atoms).

  Then in step (b1) the product of step (a1) is reacted with a compound of formula (III):

R ⁶ preferably contains only hydrogen and carbon atoms, although it is believed that R ⁶ may also contain heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents. R ⁶ is preferably alkylene or alkenylene containing 2 to 24 carbon atoms. Preferred compounds of the 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 contains only hydrogen and carbon atoms, although it is believed that R ⁷ may also contain heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents. R ⁷ is preferably arylene containing 6 to 12 carbon atoms or alkylene containing 2 to 12 carbon atoms. Preferred compounds of formula (VI) include ethylenediamine, propylenediamine, butylenediamine, pentylenediamine and hexamethylenediamine.

Before using the product of step (a1) in step (b1), any unreacted compounds of formulas (I) and (II), any solvents that may have been used, and any by-products (especially R ¹ − it is preferable to remove the OH and ^R 2 -OH compounds). Removal is preferably accomplished using a vacuum.

  In a second preferred embodiment, in step (a2), the compound of formula (I) is reacted with a compound of formula (III):

When R ¹ and R ² are linked to form a hydrocarbylene group, only one product is expected. If R ¹ and R ² are hydrocarbyl groups (not linked), an alcohol by-product is expected to occur in step (a2), and this by-product is preferably removed prior to step (b2).

  The diurea grease preferably reacts the compounds of formulas (I) and (III) in step (a2) and then in step (b2) the product of step (a2) in the presence of a base oil. Prepared by reacting with a compound of (II):

  If tetraurea grease is the desired product, in step (a2), the compounds of formula (I) and (III) are converted to compounds of formula (IV):

(Wherein R ⁵ is a hydrocarbylene containing 2 to 30 carbon atoms). Preferred R ⁵ groups are as described for the first preferred embodiment of the present invention. In step (a2), the compound of formula (I) is expected to react with the compound of formula (III), and the compound of formula (I) is expected to react with the compound of formula (IV). Then in step (b2), the reaction product of step (a2) is reacted with a compound of formula (II):

  When triurea urethane grease is the desired product, in step (a2), the compounds of formulas (I) and (III) are converted to compounds of formulas (V) and (VI):

Further reaction with (wherein R ⁶ and R ⁷ are independently selected from hydrocarbyl containing 2 to 30 carbon atoms). Preferred R ⁶ and R ⁷ groups are as described for the first embodiment of the present invention. In step (a2), the compound of formula (I) is expected to react with the compound of formula (III), the compound of formula (I) is expected to react with the compound of formula (V), and the compound of formula (I) Is expected to react with the compound of formula (VI). Then in step (b2), the reaction product of step (a2) is reacted with a compound of formula (II):

Before using the product of step (a2) in step (b2), any unreacted compounds of formulas (I) and (III), any solvents that may have been used, and any by-products (especially R ¹ − it is preferable to remove the OH and ^R 2 -OH compounds). Removal is preferably accomplished using vacuum or thorough solvent washing.

  Preferred reaction conditions in steps (a1) and (a2) are expected to be affected by the choice of compound (I). When compound (I) is diphenyl carbonate, step (a1) or (a2) is preferably carried out without a solvent or in the presence of a solvent such as toluene or dimethylformamide. This reaction is preferably carried out in the presence of a catalyst such as diphenylphosphinic acid. Phenol is expected to be produced as a reaction byproduct. Phenol by-products are expected to be removed, for example, by use of a vacuum. When compound (I) is dimethyl carbonate, it is desirable to use a catalyst such as dibutyltin methoxide, dibutyltin dilaurate or tin (II) octoate. Other catalysts that can be used include potassium t-butoxide, copper (II) acetylacetonate, DABCO BL11 and DABCO LV33.

  Preferred reaction conditions in steps (b1) and (b2) are expected to be affected by the choice of compound (I). When compound (I) is diphenyl carbonate, the reaction is preferably heated to at least 90 ° C, more preferably about 100 ° C. This reaction is preferably carried out in the absence of a catalyst. When compound (I) is dimethyl carbonate, the reaction is preferably heated to at least 130 ° C, more preferably about 140 ° C. This reaction is preferably carried out in the presence of a catalyst such as dibutyltin dilaurate. The inventors have found that additional heating is often required to convert the reaction product of step (b1) or (b2) to grease. Preferably, the reaction product of step (b1) or (b2) is heated to at least 170 ° C. and then cooled.

The base oil present in at least one of the reaction steps may be derived from minerals, derived from synthesis, or a combination thereof. The mineral-derived base oil may be a mineral oil, for example, produced by solvent refining or hydrotreating. Base oil derived synthesis typically a mixture of C ₁₀ -C ₅₀ hydrocarbon polymers, such as alpha - olefin polymers, esters types of synthetic oils may include ether type synthetic oils, and combinations thereof. Base oils can also include highly paraffinic products derived from Fischer-Tropsch.

  Preferable examples of the mineral base oil include paraffinic base oil and naphthenic base oil. Paraffinic base oils typically have carbon in the aromatic structure in the range of 1-10% (Ca), carbon in the naphthene structure in the range of 20-30% (Cn), and 60-70%. It has a proportion of carbon (Cp) in the paraffinic structure in the range. Naphthenic base oils typically have carbon (Ca) in the aromatic structure in the range of 1-20%, carbon in the naphthenic structure in the range of 30-50% (Cn), and 40-60%. It has a proportion of carbon (Cp) in the paraffinic structure in the range.

Suitable examples of base oils include medium viscosity mineral oils, high viscosity mineral oils, and combinations thereof. Medium viscosity mineral oils generally range from 5 mm ² / sec centistokes (cSt) at 100 ° C. to 15 mm ² / sec (cSt) at 100 ° C., preferably 6 mm ² / sec (cSt) at 100 ° C. And a viscosity in the range of 12 mm ² / sec (cSt) at 100 ° C., more preferably in the range of 7 mm ² / sec (cSt) at 100 ° C. and 12 mm ² / sec (cSt) at 100 ° C. High viscosity mineral oils generally range from 15 mm ² / sec (cSt) at 100 ° C. to 40 mm ² / sec (cSt) at 100 ° C., preferably 15 mm ² / sec (cSt) at 100 ° C. to 30 mm at 100 ° C. ^It has a viscosity in the range of ² / second (cSt).

  Suitable examples of mineral oils that can be conveniently used include those sold by Shell Group member companies under the names “HVI”, “MVIN”, or “HMVIP”. Polyalphaolefins and base oils of the type produced by hydroisomerization of waxes, such as those sold by Shell Group member companies under the name "XHVI" (trademark) may also be used .

  At least one of the reaction steps is performed in the presence of a base oil, preferably the last reaction step is performed in the presence of a base oil. The urea grease that is the product of the process of the present invention comprises a urea thickener and a base oil. The urea grease is preferably in the range of 2 weight percent to 25 weight percent, more preferably in the range of 3 weight percent to 20 weight percent, and most preferably in the range of 5 weight percent to 20 weight percent, based on the total weight of the urea grease. Contains weight percent urea.

  The product of the process of the present invention is urea grease. Preferably, the base grease obtained from step (b1) or step (b2) is treated with further finishing procedures such as homogenization, filtration and degassing.

  Urea made according to the method of the present invention to impart certain desirable characteristics to the urea grease, such as, for example, oxidation stability, tackiness, extreme pressure properties, corrosion inhibition, friction and wear reduction, and combinations thereof The grease may contain one or more additives in amounts normally used in this field of application. Preferably, the additive is added to the base grease prior to the finishing procedure. Most preferably, the base grease is homogenized, then the additives are added, and then the grease is treated with further homogenization.

Suitable additives include one or more extreme pressure / anti-friction agents such as zinc salts such as zinc dialkyl or diaryl dithiophosphates, borates, substituted thiadiazoles such as dialkoxyamines reacted with substituted organic phosphates. High molecular nitrogen / phosphorus compounds, amine phosphates, natural or synthetic sulfurized whale oils, sulfurized lard, sulfurized esters, sulfurized fatty acid esters, and similar sulfurized materials such as the formula (OR) ₃ P = O ( Wherein R is an alkyl, aryl or aralkyl group), and triphenylphosphorothionate; one or more overbased metal-containing detergents such as calcium alkylsalicylate or Magnesium or alkylaryl sulfonates; The reaction product of one or more ashless dispersing additives such as polyisobutenyl succinic anhydride and an amine or ester; one or more antioxidants such as hindered phenols or amines such as Phenyl alpha naphthylamine, diphenylamine or alkylated diphenylamine; one or more antirust additives, for example oxygenated hydrocarbons optionally neutralized with calcium, calcium salts of alkylated benzene sulfonates and alkylated benzene petroleum sulfonates; As well as one or more viscosity index improvers; one or more pour point depressing additives; and one or more adhesives. Also, solid materials such as graphite, finely divided MoS ₂ / talc, metal powder, and various polymers such as polyethylene wax may be added to impart special properties.

  The urea grease produced according to the method of the present invention is 0.1 weight percent to 15 weight percent, preferably 0.1 weight percent to 5 weight percent, more preferably 0.1 weight percent, based on the total weight of the urea grease. It may contain ˜2 weight percent, even more preferably 0.2 weight percent to 1 weight percent of one or more additives.

  The urea grease produced by the method of the present invention is preferably a constant velocity joint, ball joint, wheel bearing, alternator, cooling fan, ball screw, machine tool linear guide, construction equipment sliding area, and steel equipment. And in typical applications for urea greases such as bearings and gears in various other industrial machinery facilities.

  In an alternative embodiment of the invention, the urea grease comprises a compound of formula (I), a compound of formula (II) and a compound of formula (III):

Wherein R ¹ and R ² are selected from hydrocarbyl having 1 to 30 carbon atoms, or R ¹ and R ² are linked to hydrocarbylene having 1 to 30 carbon atoms. One or more reacting, wherein R ³ is selected from hydrocarbyl containing 2 to 30 carbon atoms and R ⁴ is hydrocarbylene containing 2 to 30 carbon atoms) Including many steps;
Further, the resulting urea product may be produced by a method comprising the step of dispersing in the base oil. In this modified method of the present invention, urea is synthesized from compounds (I), (II) and (III), and then the urea powder is dispersed in a base oil to form a grease.

  Figures 1, 2, 3 and 4 show reaction schemes showing the synthesis of four proposed urea greases.

  FIG. 1 shows the process of reacting diphenyl carbonate (2) with ethylenediamine (4) and octylamine (1) without a solvent under a nitrogen atmosphere. After the reaction is complete, the excess phenol is removed in vacuo. The two intermediates (3, 5) are then combined to the final tetraurea (7) by introducing methylene diphenyldiamine (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.

FIG. 2 shows a process of adding octylamine (1) and ethylenediamine (4) to an ice-cooled aqueous solution of ethylene carbonate (8). This reaction is catalyzed by (Bu ₂ Sn (OMe) ₂ ). After a short reaction time, the solvent and excess amine are removed in vacuo and the products 9 and 10 are isolated. In a further coupling reaction, products 9 and 10 and methylenediphenyldiamine (6) are coupled at 150 ° C. by the catalysis of (Bu ₂ Sn (OMe) ₂ ) and the presence of a base oil. The resulting ethylene glycol is removed in vacuo. The reaction product is heated to 170 ° C. to form a tetraurea grease.

  FIG. 3 shows a process in which dimethyl carbonate (1) and 4,4′-methylenedianiline (2) are reacted at 80 ° C. in the presence of potassium t-butoxide. Methanol is expected to be removed as a byproduct. The diphenylcarbamate product (3) is reacted with octylamine (4) in the presence of base oil and dibutyltin dilaurate at 100 ° C. to provide a grease product that is diurea in the base oil. The reaction product is heated to 170 ° C. to form a diurea grease.

  FIG. 4 shows a process in which diphenyl carbonate (1) and 4,4′-methylenedianiline (2) are reacted at 100 ° C. in the presence of diphenylphosphinic acid. Phenol is expected to 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 that is diurea in the base oil. The reaction product is heated to 170 ° C. to form a diurea grease.

  EXAMPLES Hereinafter, although an Example and a comparative example demonstrate this invention further in detail, this invention is not limited at all by these Examples.

Example 1a: Step (a2)-Synthesis of diphenylcarbamate A mixture of diphenyl carbonate (2 eq), 4,4'-methylenedianiline and diphenylphosphinic acid (5-10%) was reacted at 100 ° C overnight. (The solid melted and then formed again).

  The product was worked up by adding dimethyl ether, filtering and washing with dimethyl ether. A yield of 91-94% diphenylcarbamate was achieved.

Example 1b: Step (a2)-Synthesis of diphenylcarbamate A mixture of diphenyl carbonate (2 eq), 4,4'-methylenedianiline and diphenylphosphinic acid (10%) was reacted in toluene at 100 ° C. (1 ml / g diphenyl carbonate). The mixture was heated to reflux and after 14 hours only 7% of the starting material remained.

Example 1c: Step (b2) —Synthesis of Diurea in Base Oil 5 g of diphenylcarbamate in base oil (14.5 g) was reacted with octylamine at 110 ° C. overnight. The product was washed with 5 x 15 ml acetone. Additional base oil (14.5 g) was added and the mixture was stirred at 100 ° C. for 10 minutes and cooled to room temperature. After cooling, no grease was formed. The sample was again heated to 100 ° C. and stirred overnight at 1000 rpm. Still, no grease was formed. The material was then stirred at 170 ° C. for 30 minutes and cooled to form a grease. The properties of the grease were measured and are shown in Table 1.

Example 1d: Step (b2) —Synthesis of diurea in base oil 101 g of diphenylcarbamate prepared according to Example 1a was heated in base oil (506 g) and octylamine (60 g) at 96 ° C. overnight. did. The mixture was cooled, stirred with acetone (4 × 500 ml), allowed to settle and decanted to remove phenol and by-products (95% pure by NMR). The material was dried using a rotary evaporator, heated to 170 ° C. and then cooled 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 A mixture of diphenyl carbonate (150 g), 4,4'-methylenedianiline (69 g), and diphenylphosphinic acid (7.5 g) was reacted at 90 ° C. It was. The solid melted and a stirrable mixture was obtained. After 2-3 hours, the mixture began to become solid again. The reaction was stirred at 90 ° C. overnight (mechanical stirring).

  The next morning the mixture was solid. Base oil (198 g) was added and the mixture was stirred at 90 ° C. for 1 hour. Additional base oil was added (303.3 g). Octylamine (90.5 g) was then added. The mixture began to become milky / pink. The mixture was warmed to 104 ° C. over 6 hours 30 minutes. The mixture was suspended in acetone (II) and decanted. This was repeated several times until all the phenol was removed. The material was dried using a rotary evaporator, 130 g of base oil was added, and the mixture was heated to 170 ° C. and cooled to give a grease. The properties of the grease were measured and are shown in Table 1.

Example 3a: Step (a2)-Synthesis of dimethylcarbamate 4,4'-methylenedianiline was heated with potassium t-butoxide (4.4 equivalents) in dimethyl carbonate (pure) at 80 ° C for 0.5 hour. After filtration and washing with water, dimethylcarbamate (89%) was obtained.

Example 3b: Step (b2) —Synthesis of Diurea in Base Oil Dimethylcarbamate (65 g) prepared according to Example 3a is mixed with octylamine and dibutyltin dilaurate (added over several days) in the base oil. The diurea product was obtained with some monourea at 140 ° C. for 7 days. 498 g of grease was isolated. The properties of the grease were measured and are shown in Table 1.

Example 3c: Step (b2) and washing with acetone A sample of grease (40-50 g) from Example 3b was washed with acetone and evaporated to give 31 g with a purity of 97%. The properties of the grease were measured and are shown in Table 1.

Example 4: Synthesis of diurea and subsequent dispersion in base oil of diphenyl carbonate (10 g), 4,4'-methylenedianiline (4.6 g), and diphenylphosphinic acid (0.5 g) And reacted overnight. After the mixture was cooled to room temperature, the mixture solidified. The reaction was worked up by washing with diethyl ether (3 × 25 ml). The white material was filtered off and dried. This dicarbamate was reacted with octylamine at 105 ° C. for 2 hours. The product was washed with dichloromethane and then purified by crystallization from dimethylformamide.

  5 g of urea product was suspended in base oil (20 g). The mixture was heated to 170 ° C. over 30 minutes and then cooled to give a grease.

Grease Properties According to ASTM D217, the grease penetration and penetration were measured. A difference in consistency (difference between unmixed consistency and mixed consistency) was calculated. The dropping point was measured according to IP396. Table 1 shows the values.

  It is desirable that the consistency difference be as low as possible, and low values were achieved with some greases. The penetration values range from 247 to 340, and this range is expected to result in greases that are typically expected to fall into the NLGI grade 1, 2, or 3 category. The drop point is desirably as high as possible, with several greases achieving drop points above 300.

Claims (8)

A process for the production of urea grease comprising the compound of formula (I), the compound of formula (II) and the compound of formula (III):

Wherein R ¹ and R ² are selected from hydrocarbyl having 1 to 30 carbon atoms, or R ¹ and R ² are linked to hydrocarbylene having 1 to 30 carbon atoms. One or more reacting, wherein R ³ is selected from hydrocarbyl containing 2 to 30 carbon atoms and R ⁴ is hydrocarbylene containing 2 to 30 carbon atoms) Said production process comprising a number of steps, wherein at least one of the reaction steps is carried out in the presence of a base oil. (A1) reacting a compound of formula (I) with a compound of formula (II): and

(B1) reacting the product of step (a1) with a compound of formula (III):

The method for producing urea grease according to claim 1, wherein step (b1) is performed in the presence of a base oil. (A2) reacting a compound of formula (I) with a compound of formula (III): and

(B2) reacting the product of step (a2) with a compound of formula (II):

The process for producing urea grease according to claim 1, wherein step (b2) is carried out in the presence of a base oil.   The method according to claim 2 or 3, wherein a catalyst is present in step (a1), step (a2), step (b1) and / or step (b2).   The process according to any one of claims 2 to 4, wherein the reaction product of step (b1) or (b2) is heated to at least 170 ° C and then cooled.   6. The method of any one of claims 1-5, wherein the urea grease comprises a weight percent urea ranging from 2 weight percent to 25 weight percent, based on the total weight of urea grease.   7. A method according to any one of the preceding claims, wherein the grease is treated with one or more finishing procedures selected from homogenization, filtration and degassing.   8. A method according to any one of the preceding claims, wherein one or more additives are added to the grease.

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