US2594286A - Grease and grease base - Google Patents

Grease and grease base Download PDF

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US2594286A
US2594286A US37534A US3753448A US2594286A US 2594286 A US2594286 A US 2594286A US 37534 A US37534 A US 37534A US 3753448 A US3753448 A US 3753448A US 2594286 A US2594286 A US 2594286A
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grease
lauryl
per cent
astm
accordance
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William C Bryant
Jr Harold Frost
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Swan Finch Oil Corp
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M5/00Solid or semi-solid compositions containing as the essential lubricating ingredient mineral lubricating oils or fatty oils and their use
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/04Elements
    • C10M2201/041Carbon; Graphite; Carbon black
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/04Elements
    • C10M2201/041Carbon; Graphite; Carbon black
    • C10M2201/042Carbon; Graphite; Carbon black halogenated, i.e. graphite fluoride
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108Residual fractions, e.g. bright stocks
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08Amides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08Amides
    • C10M2215/082Amides containing hydroxyl groups; Alkoxylated derivatives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28Amides; Imides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10Semi-solids; greasy

Definitions

  • This invention relates to a. lubricating composition and particularly to a new type of grease; it also relates to compounds which may be used for producing such grease.
  • the usual commercial greases heretofore known have consisted of a semi-solid or solid combination of a petroleum product and a soap, or a mixture of soaps, with or without fillers. They have been made by various manufacturing techniques and the soap or soaps serve to produce gelation of the mixture.
  • the usual greases are made up of calcium or soda, or calcium and-soda soaps in petroleum oil or other petroleum substances.
  • the principal object of the present invention is to produce a grease which shall overcome at least some of these disadvantages and which shall have superior characteristics. to those found in the calcium and sodium greases.
  • Another object of the invention is to provide a suitable base for producing such greases.
  • the invention comprises the novel products, the specific embodiments of which are described hereinafter by way of example and in accordance with which we now prefer to practice the invention.
  • A) o l!- I I RNHownmoNHm petroleum substance such as various petroleum oils, petrolatum or like substances, possesses useful grease-like characteristics. These greases are in the form of gels and'when the compound mentioned above is present in the proportion of about 6 to 18% of the grease, it forms a smooth, semi-solidmass at room temperature.
  • the compound maybe used in other proportions, say. from, 1v to 35% of the. composition, for varying purposes. With 1% composition using. a fluid petroleum oil such as cylinder oil, the composition is smooth, thickened with respect to the oil, but is still a fluid.
  • the amides. of the above formula are prepared by amidating; corresponding polybasic acids with long; chain primary amines. Instead of using a primary amine for such amidation at each end of the-chain, we. may use. at one end of the chain a. secondary amine and substances prepared in accordance with such procedure having. the formula:
  • R and R1. are aliphatic hydrocarbon radicals having carbon. chains of a length of C8 to C18,. and" ac is;- as defined above. Substances represented by theseformulae are included in our invention.
  • amides employing long chain primary and secondary amines and their characteristics useful for making compositions or grease bases in accordance with our invention are given below. All of the following compounds have been prepared by us. All of them are opaque, amorphous solids; varying in color from white to light amber. All of them are soluble in petroleum. oils and other organic solvents and are. substantially insoluble in water. The odor of these substances varies from ammoniacal for those containing short aliphatic chains such as the N-lauryl-Nirn-butyl-sebacamide to sweetspicy for those containing all long chains attached to the nitrogen atoms. Each of these substancesm'ay be produced by the same process, forwhich a typical process example follows:
  • n H C1aHs1l 1'fi(CHz)s-Fl ICisHss 203 gms. of sebacic acid were melted and 216 gms. of stearylamine were added thereto slowly. The mass was held at a temperature to assure the half salt being liquid at all times. After all of the stearylamine had been added, all of the oleylamine (214 gms.) was added at the same time, and the temperature raised to 300 F. and maintained at 300 F. for three hours.
  • the product is an opaque, amorphous solid having a light cream color. It has a spicy odor.
  • the above example employs a temperature of 300 F. for the reaction.
  • the temperature will vary in arange of 250 F. to 350 F.
  • the temperature employed must be raised correspondingly, but all temperatures employed will be withing the range stated.
  • each of the capillary melting points given below are sharp melting points.
  • the capillary melting points will have a short range.
  • the actual range will start at a somewhat lower point, about 3 0.
  • the nitrogen content will be slightly higher, namely, up to about 0.1% nitrogen.
  • N-lauryl-N -lau ryl-azelaiimide The product is an opaque, amorphous solid having a cream color. It has a spicy odor. Its melting point is 104 C. capillary; 229 F. American wax melting point.
  • the lauryl amine was combined with the azelaic American wax melting point.
  • the palmityl amine was combined with the sebacic acid and amidated for three hours at 300 F. in accordance with the above example for the process.
  • the product is an opaque, amorphous solid having a light amber color. It has a slightly spicy odor. Its melting point is 101 C. capillary; 217 F. American wax melting point.
  • the lauryl amine and oleyl amine were combined with the azelaic acid and amidated for three hours in accordance with the above example for the process.
  • the product is an opaque, white amorphous solid. It has a spicy odor. Its melting point is 118 C. capillary; 241 F. American wax melting point.
  • the stearyl amine was combined with the itaconic acid and amidated in accordance with the above example for the process, employing a temperature of 260? F. for one hour.
  • N -lauryl-N -n-butyl-sebacamide ing a light cream color. It has a slightly ammoniacal odor. Its melting point is 114 C. capillary; 239 F. American wax melting point.
  • the lauryl and n-butyl amine were combined with the sebacic acid and amidated for three hours in accordance with the above example for the process.
  • the product is an opaque, amorphous solid having a cream color. It has a slightly ammoniacal odor.
  • the octyl amine was combined with the itaconic acid and amidated in accordance with the above example for the process, employing a temperature of 260 F. for 45 minutes.
  • the product is an opaque, amorphous solid having a cream color. It has a slightly spicy odor.
  • the lauryl amine was combined with the sebacic acid and amidated for three hours in accordance with the above example for the process.
  • the product is an opaque, amorphous solid having a cream color. It has a spicy odor.
  • the lauryl amine was combined with the succinic acid and amidated in accordance with the above example for the process, employing a temperature of 250 F. for '2 hours.
  • the 7 product is. an opaque, amorphous solid having a light .amber color... It has .a slightly ing alight amber color.
  • the product is an opaque, amorphous solid hav- It has a slightly spicy odor.
  • the oleyl amine was combined with the sebacic acid and amidated for three hours in accordance with the above example for the process.
  • the product is an opaque, amorphous solid having a cream color. It has a spicy odor.
  • the lauryl amine and palmityl I amine were combined with the azelaic acid and amidated for three hours in accordance with the above example for the process.
  • the product is an opaque, amorphous solid having a light amber color. It has a slightly spicy odor.
  • the lauryl amine and oleyl amine were combined with the itaconic acid and amidated in accordance with the above example for the process, employing a temperature of 280 'F. for one hour.
  • the product is an opaque, amorphous solid having a cream color. It has a spicy odor.
  • the lauryl amine and palmityl amine were combined with the malonic acid and amidated in accordance with the above example for the process, employing a tempera ture of 260 F. for 2 hours.
  • These amides may be prepared from substan tially pure long-chain amines which may con tain upwards of 15% of substances other than the primary amines, and polybasic acids which may contain up to 10% of substances other than the polybasic acids specified.
  • One grade of commercial .or technical lauryl amine which may be used in a mixture of amines having approximately the following composition:
  • the product is an opaque, white, amorphous solid with a slightly spicy odor.
  • the lauryl and stearyl amines were combined with the sebacic acid and amidated in accordance with the above example for the process.
  • the product is an opaque; light amber, amorphous solid with a slightly spicy odor.
  • the oleyl and palmityl amines were combined with the azelaic acid and amidated in accordance with the above example for the process.
  • the product is an opaque, cream colored, amorphous solidwith a slightly spicy odor.
  • the lauryl and palmityl amines were combined withthe sebacic acid and amidated in accordance with the above example for the process.
  • the product is an opaque, -lightamber, amorphous solid with a slightlyspicy odor.
  • the oleyl and palmityl amines were combined with the sebacic acid and amidated in accordance with the above example for the process.
  • R, R1 and a are as defined above.
  • CHQZCNHB R may be R1 in this reaction.
  • R and R1 are used herein to indicate radicals of dissimilar chain length.
  • Example 1 n Per cent N-lauryl-N1-lauryl-sebacamide 10 100/100? F. S. S. U. (Seconds Saybolt Universal) Coastal pale Oi1- The amide and the oil are heated together to 275 F. to effect solution, and the molten mass is allowed to cool to room temperature with constant slow (40 R. P. M.) agitation until the mass forms a smooth, semi-solid mass.
  • the semi-solid mass is allowed to cool to room temperature (YO-85 F.) and the mass is agitated slowly until the mass has a smooth, clear appearance and the penetration is stable according to ASTM D-217- 47 T (Amer. Soc. for Testing Materials Specification D-217-47)
  • the resultant grease had the following characteristics:
  • the difierence between ASTM D-566-42 dropping point and the Chrysler 461-C-4l dropping point is interpreted as being indicative of bleeding (syneresis) tendency of a grease.
  • the d-ifierence on the invention product listed is only nine (9) whereas for the sodium grease example the difference is sixty
  • the amide grease has a sharp melting point and does not thin out over a wide tempera-v ture range.
  • Example 3 Per cent N-tech. lauryl-Ni-tech. lauryl-sebacamide 6 3500/100 F. S. S. U. residual black oil 94
  • the same compounding technique was followed as in Example 2.
  • the other properties of this grease were similar tothose given under Example 1.
  • Example 4 Per cent N-tech. lauryl-Ni-tech. lauryl-sebacamide 4 98% 200-mesh graphite V V 14 3500/100 F. S. S. U. residual black oil 82
  • the amide and the oil were heated together to 270 F. to eifect solution, and the mass slowly stirred while cooling untilthe mass formed a heavy plastic mass.
  • the graphite was stirred in slowly to prevent lumping. After the graphite was all in, and the batch was smooth, the mass was allowed to cool to room temperature. When cool,'the mass was milled to a smooth, unctuous lubricating grease. The following characteristics appeared on test:
  • Example 5 Per cent N-tech. lauryl-Ni-tech. lauryl-sebacamide 15 70/100 F. pale paraffin oil -85 The same compounding technique was followed as in Example 1. The following characteristics appeared on-test:
  • Example 6 Per cent N-tech. lauryl-Nl-tech. lauryl-sebacamide 12 BOO/100 F. white oil 88 as in Example 2. The following characteristics appeared on test:
  • Example 7 Per cent N-tech. lauryl-Nl-tech. lauryl-azelaamide 100/100 F. S. S. U. Coastal pale oil 90 The same compounding technique was followed as in Example 1. The following characteristics appeared on test:
  • Example 9 Percent N-stearyl-Ni-stearyl-itaconamide 10 300/100 F. S. S. U. Coastal pale oil 90 The same compounding technique was followed as in Example 1. The following characteristics appeared on test:
  • Example 10 Per cent N-lauryl-Ni-mono-nbutyl-sebacamide 10 100/100 F. S. S. U. Coastal pale oil 90 The same compounding technique was followed as in Example 1. The following characteristics appeared on test:
  • Example 11 V Per Cent N-tech. lauryl-Nl-tech. lauryl sebacamide 1 4000/100 F. S. S. U. Coastal bright stock 99
  • Example 11 V Per Cent N-tech. lauryl-Nl-tech. lauryl sebacamide 1 4000/100 F. S. S. U. Coastal bright stock 99
  • Example 2 The same compounding technique was followed as in Example 1. Formed a true gel of semisolid character. With a 30 gm. cone, the following characteristics appeared on test:
  • Example 13 Per cent N-tech lauryl-Ni-tech. lauryl sebacamide 20 100/100 F. S. S. U. Coastal pale oil The same compounding technique was followed as in Example 1. The following characteristics appeared on test:
  • Example 14 Per cent N-tech. lauryl-Ni-tech. lauryl sebacamide 35 100/100 F. S. S. U. Coastal pale oil 65 The same compounding technique was followed as in Example 1. The following characteristics appeared on test:
  • Example 16 H Per cent N-lauryl-N1-sec. stearyl-sebacamide 1O BOO/100 F. S. S. U. Coastal pale oil 90 This grease was made in the same manner as in Example 1. peared on test:
  • Example 18 Per cent N-o1eyl-N1-sec. palmityl sebacamide 300/100 F. S. S. U. Coastal pale oil 90 This grease was made in the same manner as in Example 1. The following characteristics appeared on test:
  • the greases made in accordance with our 1nvention are non-metallic products. They are homogeneous; that is, the organic gelling agent is compatible in all respects with the petroleum oil or similar substance, causing the product to act as a chemical entity. Accordingly, the greases do not separate on storage or when subjected to high heat under operating conditions. In other words, they do not bleed under such conditions. They possess in general increased film strength. They show increased shear resistance, demonstrated by the fact that upon rupture of the film, it tends to heal itself quickly. They have increased oxidation stability. They give rust protection to the metal being lubricated. This has been verifiied by salt spray tests. In addition, they show better water-repellency.
  • a grease. composition comprising a petroleum lubricant and a sufficient quantity of a gelation agent to cause at least a partial gelation thereof, said agent being selected from the group consisting of in which R and R1 are aliphatic hydrocarbon radicals, R having a carbon chain of a length of C8 to C18, R1 having a carbon chain of a length of C2 to C18, and :1: equals 1 to 8.
  • a grease composition comprising a petroleum lubricant and a sufiicient quantity of a gelation agent to cause at least a partial gelation thereof, said agent having the formula where R and R1 are aliphatic hydrocarbon radicals, R having a carbon chain of a length of C8 to C18, R1 having a carbon chain of a length of C2 to C18, and x equals 1 to 8.
  • a grease composition comprising a major proportion of a petroleum lubricant and a minor proportion of a gelation agent, said agent having a formula 0 0 RNHHI (CHzhQiNHRi where R and R1 are aliphatic hydrocarbon radicals, R having a carbon chain of a length of C8 to 018, R having a carbon chain of a length of C2 to C18, and :1: equals 1 to 8.
  • a grease having about 6 to 18% of grease base having the formula where R and R1 are aliphatic hydrocarbon radicals, R having a carbon chain of a length of C8 to C18, R1 having a carbon chain of a length of C2 to C18, and :0 equals 1 to 8, and the remainderbeing composed substantially of petroleum oil.
  • a grease composed of about 10% of N-tech. lauryl-Ni-tech. lauryl-azelaamide and the remainder being composed substantially of mineral oil.
  • a grease composed of about 10% of N-tech. lauryl-N1-tech. oleyl-azelaamide and the remainder being composed substantially of mineral oil.
  • a grease composed of about 10% of N- stearyl-Ni-steary1-itaconamide and the remainder being composed substantially of mineral oil.
  • a grease composed of about 10% of N-tech. lauryl-N1 mono n butyl-sebacamide and the remainder being composed substantially of mineral oil.

Description

Patented Apr. 29, 1952 GREASE AND GREASE BASE William 0. Bryant, Garfield, N. J., and Harold Frost, Jr'., Yonkers, N. Y assignors to Swan.- Finch Oil Corporation, New York, N. Y.,, a corporation of New York No- Drawing. Application July 8', 1948, Serial No. 37,534
16' Claims. 1
This invention relates to a. lubricating composition and particularly to a new type of grease; it also relates to compounds which may be used for producing such grease.
The usual commercial greases heretofore known have consisted of a semi-solid or solid combination of a petroleum product and a soap, or a mixture of soaps, with or without fillers. They have been made by various manufacturing techniques and the soap or soaps serve to produce gelation of the mixture. The usual greases are made up of calcium or soda, or calcium and-soda soaps in petroleum oil or other petroleum substances. These known greases have certain disadvantages among which are the following: The lime soap grease and the soda soap grease have poor operating qualities at low temperatures, each producing very high starting torques at low temperatures; for example, at -20 F. Again, when the calcium greases are heated up to the melting point, the water of gel'atinboil'ed off; and when cooled, the soap tends to separate from the oil. When the sodium greases are heated up and cooled, they tend to set to a much heavier mass which is unstable to shearing forces. The calcium greases, furthermore, have relatively low dropping points. Calcium and sodium greases have little rust preventive action and the waterresistance of the sodium greases isquite low. Thus, in contact with water, such greases tend to emulsify and wash away, thus losing their. effectiveness.
The principal object of the present invention is to produce a grease which shall overcome at least some of these disadvantages and which shall have superior characteristics. to those found in the calcium and sodium greases. Another object of the invention is to provide a suitable base for producing such greases.
The invention comprises the novel products, the specific embodiments of which are described hereinafter by way of example and in accordance with which we now prefer to practice the invention.
We have found in accordance with our. invention that a composition containing a proportion of a substance having the formula:
A) o l!- I I RNHownmoNHm petroleum substance such as various petroleum oils, petrolatum or like substances, possesses useful grease-like characteristics. These greases are in the form of gels and'when the compound mentioned above is present in the proportion of about 6 to 18% of the grease, it forms a smooth, semi-solidmass at room temperature. The compound maybe used in other proportions, say. from, 1v to 35% of the. composition, for varying purposes. With 1% composition using. a fluid petroleum oil such as cylinder oil, the composition is smooth, thickened with respect to the oil, but is still a fluid.
The amides. of the above formula are prepared by amidating; corresponding polybasic acids with long; chain primary amines. Instead of using a primary amine for such amidation at each end of the-chain, we. may use. at one end of the chain a. secondary amine and substances prepared in accordance with such procedure having. the formula:
in which R and R1. are aliphatic hydrocarbon radicals having carbon. chains of a length of C8 to C18,. and" ac is;- as defined above. Substances represented by theseformulae are included in our invention. One. of the CH2 groups in. Formula A may be substituted by the group, C"=CH2, in which case the formula then reads:
Examples of the amides employing long chain primary and secondary amines and their characteristics, useful for making compositions or grease bases in accordance with our invention are given below. All of the following compounds have been prepared by us. All of them are opaque, amorphous solids; varying in color from white to light amber. All of them are soluble in petroleum. oils and other organic solvents and are. substantially insoluble in water. The odor of these substances varies from ammoniacal for those containing short aliphatic chains such as the N-lauryl-Nirn-butyl-sebacamide to sweetspicy for those containing all long chains attached to the nitrogen atoms. Each of these substancesm'ay be produced by the same process, forwhich a typical process example follows:
Process example For making N-stearyl-Nr-oleyl-sebacamide,
n H C1aHs1l 1'fi(CHz)s-Fl ICisHss 203 gms. of sebacic acid were melted and 216 gms. of stearylamine were added thereto slowly. The mass was held at a temperature to assure the half salt being liquid at all times. After all of the stearylamine had been added, all of the oleylamine (214 gms.) was added at the same time, and the temperature raised to 300 F. and maintained at 300 F. for three hours.
Yield, per cent Theoretical 95.13 Actual 95.09
acid and amidated for three hours at 300 F. in accordance with the above example for the process.
N-palmityl-N -palmityl-sebacamide i CmHasN-F(CH2)aFNC1oHa1 Analysis Yield Nitrogen Hydrogen Carbon Per cent Per cent Per cent Per cent Theoretical 4. 32 12. 96 77. 72 94. 74 Actual 4. 29 12. 91 77. 80 94. 68
The product is an opaque, amorphous solid having a light cream color. It has a spicy odor.
Its melting point is 114 C. capillary; 238 F.
represents the compound recovered after all the water of reaction has been removed. In the description of each of the substances given below, the yield obtained is given and was obtained in the same manner as that described in the above example.
The above example employs a temperature of 300 F. for the reaction. For the manufacture of the other below-listed amides correspondingly produced by the above example, the temperature will vary in arange of 250 F. to 350 F. As the chain length of the acid used increases, the temperature employed must be raised correspondingly, but all temperatures employed will be withing the range stated.
Each of the capillary melting points given below are sharp melting points. In the case of the compounds designated Tech., corresponding to the compounds mentioned below, the capillary melting points will have a short range. In these technical materials also, the actual range will start at a somewhat lower point, about 3 0.,
below the capillary melting point of the rela tively pure material. Also, in these technical compounds, the nitrogen content will be slightly higher, namely, up to about 0.1% nitrogen.-
The said examples of the amides employing long chain primary and secondary amines and their characteristics are as follows:
N-lauryl-N -lau ryl-azelaiimide The product is an opaque, amorphous solid having a cream color. It has a spicy odor. Its melting point is 104 C. capillary; 229 F. American wax melting point. In preparing this amide, the lauryl amine was combined with the azelaic American wax melting point. In preparing this amide, the palmityl amine was combined with the sebacic acid and amidated for three hours at 300 F. in accordance with the above example for the process.
N-lauryl- -oleyl azelallmide H III C iiHZ5-L I (CH2) 7FNC isHai Q t Yield, per cent Theoretical 94.28 Actual 94.20
5 The product is an opaque, amorphous solid having a light amber color. It has a slightly spicy odor. Its melting point is 101 C. capillary; 217 F. American wax melting point. In preparing this amide, the lauryl amine and oleyl amine were combined with the azelaic acid and amidated for three hours in accordance with the above example for the process.
N-stearylN -stearyl-itaconamide H H-[C-H H H Ci5H37-NC( J-(:JCNC1 H Yield, per cent Theoretical 93.94 Actual 93.90
The product is an opaque, white amorphous solid. It has a spicy odor. Its melting point is 118 C. capillary; 241 F. American wax melting point. In preparing this amide, the stearyl amine was combined with the itaconic acid and amidated in accordance with the above example for the process, employing a temperature of 260? F. for one hour.
N -lauryl-N -n-butyl-sebacamide ing a light cream color. It has a slightly ammoniacal odor. Its melting point is 114 C. capillary; 239 F. American wax melting point. In preparing this amide, the lauryl and n-butyl amine were combined with the sebacic acid and amidated for three hours in accordance with the above example for the process.
Theoretical CaHul IC--- ---.--C-I I-*CaHn t i t Yield, per cent Theoretical 90.73 Actual 90.4
The product is an opaque, amorphous solid having a cream color. It has a slightly ammoniacal odor. In preparing this amide, the octyl amine was combined with the itaconic acid and amidated in accordance with the above example for the process, employing a temperature of 260 F. for 45 minutes.
Yield, per cent 91.93 Actual 91184 Yield, per cent Theoretical 94.81 Act l 94.79
The product .is an opaque, amorphous solid having a cream color. It has a slightly spicy odor. In preparing this amide, the lauryl amine was combined with the sebacic acid and amidated for three hours in accordance with the above example for the process.
Yield, per cent Theoretical 92.63 Actual 92.59
The product is an opaque, amorphous solid having a cream color. It has a spicy odor. In. preparing this amide, the lauryl amine was combined with the succinic acid and amidated in accordance with the above example for the process, employing a temperature of 250 F. for '2 hours.
Yield, per cent Theoretical 95.02 Actual 94.98
The 7 product is. an opaque, amorphous solid having a light .amber color... It has .a slightly ing alight amber color.
spicy odor. In preparing this amide, the oleyl amine was combined with the azelaic acid and amidated for three hours in accordance with the above example for the process.
Yield, per cent Theoretical 95.11 Actual 95.03
The product is an opaque, amorphous solid hav- It has a slightly spicy odor. In preparing this amide, the oleyl amine was combined with the sebacic acid and amidated for three hours in accordance with the above example for the process.
N-lauryl-Nl-palmityl-azolatlmide H H 1 a C zH251 I-'C(CH2)1ff-C15H33 I 0 Yield, per cent Theoretical 94.14 Actual 94.10
The product is an opaque, amorphous solid having a cream color. It has a spicy odor. In preparing this amide, the lauryl amine and palmityl I amine were combined with the azelaic acid and amidated for three hours in accordance with the above example for the process.
N-lauryl-N -o1eyl-itaconamide III H-F-H H f) H C Hg5 NC( J--(:1l I-C 13H35 Yield, per cent Theoretical 93.82 Actual 93.77
The product is an opaque, amorphous solid having a light amber color. It has a slightly spicy odor. In preparing this amide, the lauryl amine and oleyl amine were combined with the itaconic acid and amidated in accordance with the above example for the process, employing a temperature of 280 'F. for one hour.
Yield, per cent Theoretical 93.11 Actual 93.01
The product is an opaque, amorphous solid having a cream color. It has a spicy odor. In preparing this amide, the lauryl amine and palmityl amine were combined with the malonic acid and amidated in accordance with the above example for the process, employing a tempera ture of 260 F. for 2 hours.
These amides may be prepared from substan tially pure long-chain amines which may con tain upwards of 15% of substances other than the primary amines, and polybasic acids which may contain up to 10% of substances other than the polybasic acids specified. One grade of commercial .or technical lauryl amine which may be used in a mixture of amines having approximately the following composition:
Per Per cent cent Primary amines 85 Octyl min 8 Decylamina 9 Dodecylnmine 47 Tetradecylamine 18 Hexadecylamine 8 Octadecyl mine Octfldecenylamine 6 Secondary amines Total 100 This mixed aminewould, of course, produce a mixture of corresponding amides with the dibasic acid selected.
Examples of amides employing -secondary amines in accordance with the formula where R,'R1 and a: are as defined above, are as follows:
N-lauryl-N -sec. stearyl sebacamide Yield, per cent Theoretical 96.04 Actual 96.01
The product is an opaque, white, amorphous solid with a slightly spicy odor. In preparing this amide, the lauryl and stearyl amines were combined with the sebacic acid and amidated in accordance with the above example for the process.
N-oleyl- -sec. palmityl-azelafimide lB 35 -E 2)7 fi' 1fiH33)2 Yield, per cent Theoretical 96.09 Actual 96.04
The product is an opaque; light amber, amorphous solid with a slightly spicy odor. In preparing this amide, the oleyl and palmityl amines were combined with the azelaic acid and amidated in accordance with the above example for the process.
N-lauryl-N sec. palmityl sebacamide i 12H25N:i-( H2) sfi-N( isHsa)z Yield, per cent Theoretical 95.77 Actual 95.70
The product is an opaque, cream colored, amorphous solidwith a slightly spicy odor. In preparing this amide, the lauryl and palmityl amines were combined withthe sebacic acid and amidated in accordance with the above example for the process.
N-oley1-N -sec. palmityl sebacamide H C 1sHs5-Il% (GH2) B (I:'|N (CisHia) 2 o 0 Yield, per cent Theoretical 96.14 Actual 96.11
8 The product is an opaque, -lightamber, amorphous solid with a slightlyspicy odor. In preparing this amide, the oleyl and palmityl amines were combined with the sebacic acid and amidated in accordance with the above example for the process.
The reaction which occurs for the production of the material in accordance with Formula A above'is' as follows:
where R, R1 and a: are as defined above. Of
course, if R and R1 represent the same radical,
the equation. can be simplified to recite If a secondary amine is used, the reaction is represented as follows:
o E ll 21110 mm (CHQZCNHB R may be R1 in this reaction. In other words, R and R1 are used herein to indicate radicals of dissimilar chain length.
The following are examples of the manner in which we now prefer to practice our invention for the manufacture of grease. These examples are illustrative and the invention is not to be considered as confined thereto except as indicated in the appended claims.
Example 1 n Per cent N-lauryl-N1-lauryl-sebacamide 10 100/100? F. S. S. U. (Seconds Saybolt Universal) Coastal pale Oi1- The amide and the oil are heated together to 275 F. to effect solution, and the molten mass is allowed to cool to room temperature with constant slow (40 R. P. M.) agitation until the mass forms a smooth, semi-solid mass.
The semi-solid mass is allowed to cool to room temperature (YO-85 F.) and the mass is agitated slowly until the mass has a smooth, clear appearance and the penetration is stable according to ASTM D-217- 47 T (Amer. Soc. for Testing Materials Specification D-217-47) The resultant grease had the following characteristics:
Penetration 5000 vstrokes work- Water absorption (Chrysler 461- BEC running torque at 20 F.
' Water For puirposes of comparison. we give below corresponding characteristics, respectively, of lime and soda soap greases:
A lime soap grease. 10% soap, 90% 1.00/ 100 F. S. S. U- Coastal pale oil had the following characteristics Penetration 5000 strokes working 420 Penetration ASTM D2l747-T 330 D/P ASTM D-566-42 188 F. D/P Chrysler 461-C-3l 181 F. BEC'starting torque at 70 F..... 540 dynes BEC running torque at 70 F 120 dynes BEC starting torque at 20 F- Over 2700 dynes No stable point (continued to v drop) Corrosion test-grease1i-. S.
B. 5791b (Federal Specification B'ook VV'L) Rust protection 10% salt spray absorption Chrysler 46 lC-41 1 A sodium soap grease. sodas 021p. 90%
Nil 8 hrs. failed 100/100 F. S. S. U. Coastal pale oil had the fol- Over 420 540 dynes 180 dynes Over 2700 dynes 600 dynes Nil 10 hrs. failed At 60% turned to liquid emulsion The above characteristics show that the amide grease is superior to the calcium grease in all respects and is superior to the sodium grease in many respects. With respect to the sodium grease, it is noted that there is very little syneresis in the amide grease as compared with the sodium grease, as may be seen by comparing the dropping points of the two. The difierence between ASTM D-566-42 dropping point and the Chrysler 461-C-4l dropping point is interpreted as being indicative of bleeding (syneresis) tendency of a grease. The greater the numerical difference of the two dropping points, the greater the bleeding tendency. As can be seen from the data above, the d-ifierence on the invention product listed is only nine (9) whereas for the sodium grease example the difference is sixty Furthermore, the amide grease has a sharp melting point and does not thin out over a wide tempera-v ture range. The amide greases when compounded as above revert to their original gel structure after being heated to the melting point and allowed to cool, whereas the calcium greases show separation of the soap from the oil upon The same compounding technique was followed 10 The amide and the oil were heated together to 270 F. to achieve complete solution. The mixture was allowed to cool to room temperature over night. The solid mass was milled out to a smooth, buttery consistency. The following characteristics appeared on test:
Penetration AS'IM D-217-47-T 340 D/P ASTM D-566-42 F 226 The other properties of this grease were similar to those given under Example 1.
Example 3 Per cent N-tech. lauryl-Ni-tech. lauryl-sebacamide 6 3500/100 F. S. S. U. residual black oil 94 The same compounding technique was followed as in Example 2. The following characteristics I appeared on test: 7 I I Penetration. ASTM D-Zl 747T -a 330 D/P AS'IM D- 566-42 F 222 The other properties of this grease were similar tothose given under Example 1.
Example 4 Per cent N-tech. lauryl-Ni-tech. lauryl-sebacamide 4 98% 200-mesh graphite V V 14 3500/100 F. S. S. U. residual black oil 82 The amide and the oil were heated together to 270 F. to eifect solution, and the mass slowly stirred while cooling untilthe mass formed a heavy plastic mass. The graphite was stirred in slowly to prevent lumping. After the graphite was all in, and the batch was smooth, the mass was allowed to cool to room temperature. When cool,'the mass was milled to a smooth, unctuous lubricating grease. The following characteristics appeared on test:
Penetration ASTM D-217-47-T s10 D/P ASTM D-566-42 FL- .222
The other properties of this grease were similar to those given under Example 1.
Example 5 Per cent N-tech. lauryl-Ni-tech. lauryl-sebacamide 15 70/100 F. pale paraffin oil -85 The same compounding technique was followed as in Example 1. The following characteristics appeared on-test:
Penetration ASTM D-217-47-T 275 D/P ASTM D-566-42 F 230 The other properties of this grease were similar to those given under Example 1.
Example 6 Per cent N-tech. lauryl-Nl-tech. lauryl-sebacamide 12 BOO/100 F. white oil 88 as in Example 2. The following characteristics appeared on test:
Penetration ASTM D-2l7-47-T 29o D/P eros ace-42. F 231 r v 11 The other properties of this grease were similar to those given under Example 1.-
Example 7 Per cent N-tech. lauryl-Nl-tech. lauryl-azelaamide 100/100 F. S. S. U. Coastal pale oil 90 The same compounding technique was followed as in Example 1. The following characteristics appeared on test:
Penetration ASTM D-217-47-T 345 D/P ASTM D-566-42 ..F 205 The other properties of this grease were similar to those given under Example 1.
. Example 8 Per cent N-tech. lauryl-N1-tech. oleyl-azelaamide 10 160/100" F. S. S. U. solvent extracted Mid.-
continent pale oil 90 The same compounding technique was followed as in'Example 1. The following characteristics appeared on test:
Penetration ASTM D217-4'7T v 325 D/P ASTM D-566-42 F 200 The other properties of this grease were similar to those given under Example l.
Example 9 Percent N-stearyl-Ni-stearyl-itaconamide 10 300/100 F. S. S. U. Coastal pale oil 90 The same compounding technique was followed as in Example 1. The following characteristics appeared on test:
Penetration ASTM D-217-4'7-T 350 D/P ASTM D566-42 F 203 The other properties of this grease were similar to those given under Example 1.
Example 10 Per cent N-lauryl-Ni-mono-nbutyl-sebacamide 10 100/100 F. S. S. U. Coastal pale oil 90 The same compounding technique was followed as in Example 1. The following characteristics appeared on test:
Penetration-ASTM D-217-47-T 1 275 D/P ASTM D-566-42 F 265 The other properties of this grease were similar to those given under Example 1.
I Example 11 V Per Cent N-tech. lauryl-Nl-tech. lauryl sebacamide 1 4000/100 F. S. S. U. Coastal bright stock 99 The same compounding technique was followed as in Example 1. Formed a solution that was a 'truegel but was of a semi-fluid consistency. Using a 30 gm. cone, in place of the'150'gm.
. 1'2 cone, the following characteristics appeared on test:
Penetration Modified ASTM D-217-47 330 D/P ASTM D-566-42 F 135 The other properties of this grease were similar to those given under Example 1.
The same compounding technique was followed as in Example 1. Formed a true gel of semisolid character. With a 30 gm. cone, the following characteristics appeared on test:
Penetration ASTM D-217-47 300 D/P ASTM D-566-42 F 15 5 The other properties of this grease were similar to those given under Example 1.
Example 13 Per cent N-tech lauryl-Ni-tech. lauryl sebacamide 20 100/100 F. S. S. U. Coastal pale oil The same compounding technique was followed as in Example 1. The following characteristics appeared on test:
Penetration ASTM D-21'7-4'7 275 D/P ASTM D-56642 F.. 245
The other properties of this grease were similar to those given in Example 1.
Example 14 Per cent N-tech. lauryl-Ni-tech. lauryl sebacamide 35 100/100 F. S. S. U. Coastal pale oil 65 The same compounding technique was followed as in Example 1. The following characteristics appeared on test:
Penetration ASTM D-217-47 205 D/P ASTM D-566-42 F 265 The other properties of this grease were similar to those given in Example 1.
Example 15 Per cent N-lauryl-Ni-palmityl malonamide 10 500/100" F. S. S. U. Coastal pale oil 90 .100
The same compounding technique was followed as in Example' 2. The following characteristics appeared on test:
- Penetration ASTM D-2 174'l 355 D/P ASTM 13:566-42 F The other properties of this grease were similar to' those given. in Example 1..
----Although we prefer the compounds made with primary amines, we have also produced useful compounds employing the secondary amines, as follows:
Example 16 H Per cent N-lauryl-N1-sec. stearyl-sebacamide 1O BOO/100 F. S. S. U. Coastal pale oil 90 This grease was made in the same manner as in Example 1. peared on test:
Penetration ASTM D-2l7-47- T 340 D/P ASTM D-566-42'. F.. 211 The other properties of this grease were similar to those given in Example 1.
The other properties of this grease were similar to those given-in Example 1.
Example 18 Per cent N-o1eyl-N1-sec. palmityl sebacamide 300/100 F. S. S. U. Coastal pale oil 90 This grease was made in the same manner as in Example 1. The following characteristics appeared on test:
Penetration ASTM D-217-47-T 306 D/P ASTM D-566-42 F 209 The other properties of this grease were similar to those given in Example 1.
The greases made in accordance with our 1nvention, as pointed out, are non-metallic products. They are homogeneous; that is, the organic gelling agent is compatible in all respects with the petroleum oil or similar substance, causing the product to act as a chemical entity. Accordingly, the greases do not separate on storage or when subjected to high heat under operating conditions. In other words, they do not bleed under such conditions. They possess in general increased film strength. They show increased shear resistance, demonstrated by the fact that upon rupture of the film, it tends to heal itself quickly. They have increased oxidation stability. They give rust protection to the metal being lubricated. This has been verifiied by salt spray tests. In addition, they show better water-repellency. They also possess reversibility, namely, the grease will melt and then on cooling will revert to its gel form. They have a wide temperature range of operation. Tests both at low and high temperatures have demonstrated this. Due to the fact that the grease bases contain at least one hydrogen atom attached to one or more of the nitrogen groups, these bases are polar which will cause the lubricant, even in melted condition, to adhere to the metal being lubricated. In addition, tests have shown that the greases possess greater oiliness.
The following characteristics ap- Subject matter described but not claimed herein is claimed in copending application Serial No. 220,124, filed April 3, 1951.
What we claim is:
1.. A grease. composition comprising a petroleum lubricant and a sufficient quantity of a gelation agent to cause at least a partial gelation thereof, said agent being selected from the group consisting of in which R and R1 are aliphatic hydrocarbon radicals, R having a carbon chain of a length of C8 to C18, R1 having a carbon chain of a length of C2 to C18, and :1: equals 1 to 8.
2. A grease composition comprising a petroleum lubricant and a sufiicient quantity of a gelation agent to cause at least a partial gelation thereof, said agent having the formula where R and R1 are aliphatic hydrocarbon radicals, R having a carbon chain of a length of C8 to C18, R1 having a carbon chain of a length of C2 to C18, and x equals 1 to 8.
3. A grease composition comprising a major proportion of a petroleum lubricant and a minor proportion of a gelation agent, said agent having a formula 0 0 RNHHI (CHzhQiNHRi where R and R1 are aliphatic hydrocarbon radicals, R having a carbon chain of a length of C8 to 018, R having a carbon chain of a length of C2 to C18, and :1: equals 1 to 8.
4. A grease having a grease base in the proportion of 1 to 35% of the total weight of the grease having the formula where R and R1 are aliphatic hydrocarbon radicals, R having a carbon chain of a length of C8 to C18, R1 having a carbon chain of a length of C2 to C18, and as equals 1 to 8, and the major proportion of the remainder of the grease being composed of petroleum oil.
5. A grease having about 6 to 18% of grease base having the formula where R and R1 are aliphatic hydrocarbon radicals, R having a carbon chain of a length of C8 to C18, R1 having a carbon chain of a length of C2 to C18, and :0 equals 1 to 8, and the remainderbeing composed substantially of petroleum oil.
6. A grease having up to 14% graphite and about 4% technical N-lauryl-N1-lauryl-sebacamide, the remainder of the grease being composed substantially of mineral oil.
7. A grease composed of about 10% of N-tech. lauryl-Ni-tech. lauryl-azelaamide and the remainder being composed substantially of mineral oil.
8. A grease composed of about 10% of N-tech. lauryl-N1-tech. oleyl-azelaamide and the remainder being composed substantially of mineral oil.
9. A grease composed of about 10% of N- stearyl-Ni-steary1-itaconamide and the remainder being composed substantially of mineral oil.
10. A grease composed of about 10% of N-tech. lauryl-N1 mono n butyl-sebacamide and the remainder being composed substantially of mineral oil.
11. As a new composition, a mixture containing a minor proportion of a substance having the formula where R and R1 are aliphatic hydrocarbon radicals, R having a carbon chain of a length of C8 to C18, R1 having a carbon chain of a length of C2 to C18, the balance of the composition being a petroleum lubricant.
12. A process in accordance with claim 2 in which the gelation agent is N-lauryl-Ni-laurylazelaiimide.
13. A process in accordance with claim 2 in which the gelation agent is N-lauryl-Ni-oleylazelaamide.
14. A process in accordance with claim 2 in 16 which the gelation agent is N-lauryl-Nin-butylsebacamide.
15. A process in accordance with claim 2 in which the gelation agent is N-laurylNi-laurylsebacamide.
16. A process in accordance with claim 2 in which the gelation agent is N-stearylN1-steary1- itaconamide.
- WILLIAM C. BRYANT.
HAROLD FROST, JR.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 1,659,149 Nill Feb. 14, 1928 1,937,463 Nill Nov. 28, 1933 2,109,941 DAlelio Mar. 1, 1938 2,304,475 Pool Dec. 8, 1942 2,364,737 McGrew Dec. 12, 1944 2,371,104 Kienle et al Mar. 6, 1945 2,412,708 Blair Dec. 17, 1946 2,417,833 Lincoln et a1 Mar. 25, 1947 2,490,744 Trigg et a1. Dec. 6, 1949

Claims (1)

1. A GREASE COMPOSITION COMPRISING A PETROLEUM LUBRICANT AND A SUFFICIENT QUANTITY OF A GELATION AGENT TO CAUSE AT LEAST A PARTIAL GELATION THEREOF, SAID AGENT BEING SELECTED FROM THE GROUP CONSISTING OF
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Cited By (21)

* Cited by examiner, † Cited by third party
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US2698300A (en) * 1951-06-28 1954-12-28 California Research Corp Greases thickened with acyl ureas
US2709157A (en) * 1951-06-28 1955-05-24 California Research Corp Greases thickened with phenylene diamides
US2710839A (en) * 1952-11-01 1955-06-14 Standard Oil Co Aryl-urea thickened greases
US2744071A (en) * 1952-02-27 1956-05-01 Exxon Research Engineering Co Lubricating oil additives
US2752312A (en) * 1952-08-19 1956-06-26 California Research Corp Polyamide-polyamate-thickened grease
US2756213A (en) * 1952-08-19 1956-07-24 California Research Corp Amate-dicarboxylate-thickened grease
US2830955A (en) * 1955-11-23 1958-04-15 California Research Corp Polyamide-thickened grease
US2830954A (en) * 1955-11-23 1958-04-15 California Research Corp Polyamide grease composition
US2908711A (en) * 1956-06-14 1959-10-13 Gulf Research Development Co Itaconic acid-amine reaction product
US2971910A (en) * 1957-12-16 1961-02-14 Shell Oil Co Lubricating compositions
US2977309A (en) * 1955-04-21 1961-03-28 Monsanto Chemicals Lubricating oil containing branched chain alkyl amine derivatives of dicarboxylic acids
DE1103336B (en) * 1957-09-19 1961-03-30 Nat Lead Co Process for the production of organic salts which have swelling, gelling and dispersing properties for organic liquids
US3226437A (en) * 1961-09-05 1965-12-28 Gulf Oil Corp N,n'-bisolelyloxamide
US3910847A (en) * 1972-10-02 1975-10-07 Sun Ventures Inc Tertiary diamides
US3933663A (en) * 1972-10-02 1976-01-20 Sun Ventures, Inc. Tertiary diamide as swelling agent for elastomeric seal
US4396516A (en) * 1979-10-09 1983-08-02 Nippon Oil Company, Ltd. Lubricant
US4517378A (en) * 1983-06-30 1985-05-14 E. I. Du Pont De Nemours And Company Curing agent for fluorocarbon polymer coating compositions
EP0467533A1 (en) * 1990-07-18 1992-01-22 Rheox International, Inc. Polyamide compositions and sealant formulations comprising them
EP1803792A1 (en) * 2004-10-20 2007-07-04 Porite Corporation Heat reversible gel-like lubricating composition, process for producing the same, and bearing lubricant and bearing system using said composition
WO2008070307A3 (en) * 2006-10-23 2008-11-27 Lubrizol Corp Antiwear agent and lubricating composition thereof
US20090176668A1 (en) * 2006-03-24 2009-07-09 Japan Energy Corporation Semi-solid lubricant composition for transmission element and mechanical system provided with the same

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US2109941A (en) * 1936-06-05 1938-03-01 Du Pont Preparation of amides
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US1659149A (en) * 1923-05-04 1928-02-14 Frederick C Acker Lubricating composition
US1937463A (en) * 1927-12-07 1933-11-28 P E Selby Inc Lubricating composition and method of making same
US2109941A (en) * 1936-06-05 1938-03-01 Du Pont Preparation of amides
US2304475A (en) * 1939-10-20 1942-12-08 Armour & Co High molecular weight aliphatic diamide of sebacic acid and process of preparing same
US2364737A (en) * 1940-10-11 1944-12-12 Du Pont Ethers
US2417833A (en) * 1944-04-22 1947-03-25 Continental Oil Co Lubricant
US2412708A (en) * 1944-10-16 1946-12-17 Petrolite Corp Lubricating oils
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Cited By (26)

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Publication number Priority date Publication date Assignee Title
US2698300A (en) * 1951-06-28 1954-12-28 California Research Corp Greases thickened with acyl ureas
US2709157A (en) * 1951-06-28 1955-05-24 California Research Corp Greases thickened with phenylene diamides
US2744071A (en) * 1952-02-27 1956-05-01 Exxon Research Engineering Co Lubricating oil additives
US2752312A (en) * 1952-08-19 1956-06-26 California Research Corp Polyamide-polyamate-thickened grease
US2756213A (en) * 1952-08-19 1956-07-24 California Research Corp Amate-dicarboxylate-thickened grease
US2710839A (en) * 1952-11-01 1955-06-14 Standard Oil Co Aryl-urea thickened greases
US2977309A (en) * 1955-04-21 1961-03-28 Monsanto Chemicals Lubricating oil containing branched chain alkyl amine derivatives of dicarboxylic acids
US2830955A (en) * 1955-11-23 1958-04-15 California Research Corp Polyamide-thickened grease
US2830954A (en) * 1955-11-23 1958-04-15 California Research Corp Polyamide grease composition
US2908711A (en) * 1956-06-14 1959-10-13 Gulf Research Development Co Itaconic acid-amine reaction product
DE1103336B (en) * 1957-09-19 1961-03-30 Nat Lead Co Process for the production of organic salts which have swelling, gelling and dispersing properties for organic liquids
US2971910A (en) * 1957-12-16 1961-02-14 Shell Oil Co Lubricating compositions
US3226437A (en) * 1961-09-05 1965-12-28 Gulf Oil Corp N,n'-bisolelyloxamide
US3910847A (en) * 1972-10-02 1975-10-07 Sun Ventures Inc Tertiary diamides
US3933663A (en) * 1972-10-02 1976-01-20 Sun Ventures, Inc. Tertiary diamide as swelling agent for elastomeric seal
US4396516A (en) * 1979-10-09 1983-08-02 Nippon Oil Company, Ltd. Lubricant
US4517378A (en) * 1983-06-30 1985-05-14 E. I. Du Pont De Nemours And Company Curing agent for fluorocarbon polymer coating compositions
EP0467533A1 (en) * 1990-07-18 1992-01-22 Rheox International, Inc. Polyamide compositions and sealant formulations comprising them
EP1803792A1 (en) * 2004-10-20 2007-07-04 Porite Corporation Heat reversible gel-like lubricating composition, process for producing the same, and bearing lubricant and bearing system using said composition
EP1803792A4 (en) * 2004-10-20 2010-07-28 Porite Corp Heat reversible gel-like lubricating composition, process for producing the same, and bearing lubricant and bearing system using said composition
US20090069203A1 (en) * 2004-10-20 2009-03-12 Porite Corporation Heat reversible gel-like lubricating composition, process for producing the same, and bearing lubricant and bearing system using said composition
JPWO2007116642A1 (en) * 2006-03-24 2009-08-20 株式会社ジャパンエナジー Semi-solid lubricant composition for transmission element and mechanical system provided with the same
US20090176668A1 (en) * 2006-03-24 2009-07-09 Japan Energy Corporation Semi-solid lubricant composition for transmission element and mechanical system provided with the same
US7973000B2 (en) * 2006-03-24 2011-07-05 Japan Energy Corporation Semi-solid lubricant composition for transmission element and mechanical system provided with the same
WO2008070307A3 (en) * 2006-10-23 2008-11-27 Lubrizol Corp Antiwear agent and lubricating composition thereof
US8304374B2 (en) 2006-10-23 2012-11-06 The Lubrizol Corporation Antiwear agent and lubricating composition thereof

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