US2328727A - Soluble oil - Google Patents
Soluble oil Download PDFInfo
- Publication number
- US2328727A US2328727A US351990A US35199040A US2328727A US 2328727 A US2328727 A US 2328727A US 351990 A US351990 A US 351990A US 35199040 A US35199040 A US 35199040A US 2328727 A US2328727 A US 2328727A
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- US
- United States
- Prior art keywords
- oil
- soluble
- soap
- water
- alkali metal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
Definitions
- This invention relates to soluble oils comprising petroleum oils which disperse readily when added to water. Oils of this type are used, for example, in the preparation of aqueous emulsions for use as a, cooling and lubricating fluid in metal working operations, such as the grinding, cutting, and turning of metals, and as a slushing oil for the protection of metal surfaces against oxidation.
- the emulsion In metal working, it is essential that the emulsion provide sufflcient lubrication and cooling, and the emulsion should not corrode or rust metals. In such operations as grinding operations, the emulsion should permit rapid settling of the removed metal and abrasive particles so that they will not be carried over to subsequent work, should keep the grinding surfaces clean, and should wet the work uniformly. The emulsion should not be materially aifected by hard water. Some of the prior emulsions were unstable in hard water, and an attempt to remedy this by softening the water resulted in objectionable foaming.
- a soluble oil comprising a petroleum oil, mahogany sulfonates, an alkali metal soap, and an alkylolamine. It has been found that the combination of an alkylolamine, such as triethanolamine, and a substantially neutral alkali metal soap, such as sodium resinate or rosin soap, has a unique rust inhibiting value and that the addition of an alkali metal hydroxide to compositions containing this combination further improves the rust inhibiting characteristics.
- an alkylolamine such as triethanolamine
- a substantially neutral alkali metal soap such as sodium resinate or rosin soap
- alkylolamines In addition to triethanolamine, other alkylolamines, such as monoand di-ethanolamines and the propanolamines, have been found to produce excellent results in combination with the other ingredients which make up the soluble oil of this invention. These alkylolamines increase the stability of the emulsion formed from the soluble oil, as well as inhibit the corrosion and rusting of metals. In the soluble oil the alkylolamines promote uniformity in the composition and prevent the separation of soap at low temperatures.
- substantially neutral alkali metal soap a rosin soap is preferred since this type of soap has very good grinding qualities and also is quite inexpensive.
- other water-soluble, substantially neutral soaps such as naphthenate soaps and the soaps of the fatty acids, such as palmitic, stearic, and oleic acids, may be used.
- the presence of substantial amounts of the soap are essential for emulsion stability.
- an important characteristic of the soap is that it cooperates with alkylolamines in the effective inhibiting of corrosion and rust formation. While considerable latitude is allowable in the selection of the soap, the soaps of the alkylolamines are to be avoided in view of their pronounced tendency toward the formation of foams.
- the alkylolamine soaps also do not permit ready settling of solid particles in the emulsion, such solid particles being the result of grindmetal sulfonates, such ing processes, etc. Therefore, there should be no acid in the composition available for the formation of soaps with the alkylolamines.
- the mahogany sulfonates in the composition are the primary emulsifying agents, but emulsification is also promoted by the alkali metal soaps and the alkylolamines.
- Mahogany sulfonates as is well known in the art, are the oil-soluble sulfonates formed in the sulfonation of petroleum oils. They are ordinarily prepared as alkali as sodium sulfonates, and they may be purified by several known methods. It is contemplated to use either the pure mahogany sulfonates or any of the commercial grades of varying degrees of purity. A commercial product containing about mahogany sulfonates has been found to be effective.
- the petroleum oil in the soluble oil may be those commonly used in soluble oils, such as, for example, a petroleum lubricating oil having a viscosity of about '70 seconds at F. Saybolt Universal.
- a small amount of water is preferably used to make the soluble oil fluid and to prevent oil separation, or Stratification of the emulsion, upon mixing the soluble oil with larger amounts of water.
- Mahogany sulfonates 5 to 15 Neutral alkali metal soap 2- to 6 Alkylolamine l. 0.5 to 4 Water 1 to 5 Petroleum oil Balance
- rosin is dissolved in a portion'of the petroleum oil at a temperature of about 200 F.
- the mahogany soaps which are readily soluble in this mixture,
- a soluble oil which is particularly efiective in grinding processes has the following composition:
- an alkali metal hydroxide it is preferred to add from 0.01 to 0.2% of an alkali metal hydroxide to any of the soluble oils prepared according to the invention wherever minimum corrosion and rusting of metals is desired. It is to be understood, how- 'ever, that the mere presence of an excess of an alkali metal hydroxide in any emulsion does not necessarily result in the prevention of rust formation. An emulsion containing no free alkylolamine is not improved with respect to rust prevention by the presence of excess caustic. Therefore, the improvement obtained when an excess of an alkali metal hydroxide is added in v the preparation of the composition of this in- When the use of very hard water is necessary, it is therefore desirable to increase the proportion of sodium resinate. For example, increasing the proportion of sodium resinate from 2.65% to 5.3% results in a completely stable emulsio where water of high hardness is used.
- a soluble oil comprising a petroleum oil, mahogany sulfonates, a water-soluble soap, an alkylolamine in amounts suflicient to impart antirusting properties, and an alkali metal hydroxide.
- a soluble oil comprising a petroleum oil, mahogany sulfonates, a water-soluble soap, an alkylolamine in amounts suflicient to impart antirusting properties, an'alkali metal hydroxide, and water.
- a soluble 011 comprising a petroleum oil, mahogany sulfonates, a rosin soap, triethanolamine in amounts suflicient to impart anti-rustin properties, and an alkali metal hydroxide.
- a soluble oil comprising a petroleum oil, mahogany sulfonates, a rosin soap, triethanolamine in amounts sufficient to impart anti-rusting properties, an alkali metal hydroxide, and water.
- a soluble 011 comprising a petroleum oil, a water-soluble soap, triethanolamine in amounts suilicient to impart anti-rusting properties, and an alkali metal hydroxide.
- a soluble oil comprising a petroleum oil, 5 to 15% mahogany sulfonates, 2 to 6% watersoluble alkali metal soap, and 0.5 to 4% alkylolamine, the petroleum oil constituting substantially all of the remainder.
- a soluble oil comprising a petroleum oil, 5 to 15% mahogany sulfonates, 2 to 6% neutral alkali metal rosin soap, and 0.5 to 4% triethanolamine, the petroleum oil constituting substantially all of the remainder.
- a soluble oil comprising a petroleum oil, 5 to 15% mahogany sulfonates, 2 to 6% rosin soap, 0.5 to 4% triethanolamine, and 0.01 to 0.2% alkali metal hydroxide, the petroleum oil constituting substantially all of the remainder.
- a soluble oil comprising a petroleum oil, 5 to 15% mahogany sulfonates, 2 to 6% rosin soap, 0.5 to 4% triethanolamine, 0.01 to 0.2% alkali metal hydroxide, and 1 to 5% water, the petroleum oil constituting substantially all of the remainder.
- a soluble oil comprising a petroleum oil, about 15% commercial mahogany sulfonates, about 2.65% rosin soap, about 1% triethanolamine, about 2% water, and about'0.1% sodium hydroxide, the petroleum oil constituting substantially all of the remainder.
- a soluble oil comprising a petroleum oil
- a soluble oil according to claim 11 con taining from 0.1 to 0.2% butyl ether of diethylene glycol.
- a soluble oil comprising petroleum oil, 5 to 15% mahogany sulfonate, 2 to 6% neutral alkali metal rosin soap; 0.5 to 4% alkylolamine, and 1 to 5% water, the petroleum oil constituting substantially all of the remainder.
- a soluble oil comprising petroleumoil, 5 to 15% mahogany sulfonate, 2 to 6% alkali metal rosin soap, said soap being completely saponifled, 0.5 to 4% alkylolamine, and 1 to 5% water, the petroleum oil constituting substantially all of the remainder.
- a soluble oil comprising petroleum oil, mahogany sulfonate, 4 to 6% rosin soap, alkylolamine in amounts sufficient to impart anti-rusting properties, and a small amount of butyl ether of diethylene glycol, the petroleum oil constituting substantially all of the remainder.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Description
Patented Sept. 7, 1943 UNITED STATES PATENT OFFICE r. by p ny. ware mesne assignments, to The Texas Com- New York, N. Y., a corporation of Dela- No Drawing. Application August 9, 1940, Serial No. 351,990
17 Claims.
This invention relates to soluble oils comprising petroleum oils which disperse readily when added to water. Oils of this type are used, for example, in the preparation of aqueous emulsions for use as a, cooling and lubricating fluid in metal working operations, such as the grinding, cutting, and turning of metals, and as a slushing oil for the protection of metal surfaces against oxidation.
In metal working, it is essential that the emulsion provide sufflcient lubrication and cooling, and the emulsion should not corrode or rust metals. In such operations as grinding operations, the emulsion should permit rapid settling of the removed metal and abrasive particles so that they will not be carried over to subsequent work, should keep the grinding surfaces clean, and should wet the work uniformly. The emulsion should not be materially aifected by hard water. Some of the prior emulsions were unstable in hard water, and an attempt to remedy this by softening the water resulted in objectionable foaming.
It is an object of this invention to produce a soluble oil which is superior to soluble oils used in the past, since none of the prior soluble oils fully met the various requirements.
It has now been discovered that the requirements enumerated and other requirements are particularly well met by a soluble oil comprising a petroleum oil, mahogany sulfonates, an alkali metal soap, and an alkylolamine. It has been found that the combination of an alkylolamine, such as triethanolamine, and a substantially neutral alkali metal soap, such as sodium resinate or rosin soap, has a unique rust inhibiting value and that the addition of an alkali metal hydroxide to compositions containing this combination further improves the rust inhibiting characteristics.
In addition to triethanolamine, other alkylolamines, such as monoand di-ethanolamines and the propanolamines, have been found to produce excellent results in combination with the other ingredients which make up the soluble oil of this invention. These alkylolamines increase the stability of the emulsion formed from the soluble oil, as well as inhibit the corrosion and rusting of metals. In the soluble oil the alkylolamines promote uniformity in the composition and prevent the separation of soap at low temperatures.
As the substantially neutral alkali metal soap, a rosin soap is preferred since this type of soap has very good grinding qualities and also is quite inexpensive. However, other water-soluble, substantially neutral soaps, such as naphthenate soaps and the soaps of the fatty acids, such as palmitic, stearic, and oleic acids, may be used. The presence of substantial amounts of the soap are essential for emulsion stability. As noted above, an important characteristic of the soap is that it cooperates with alkylolamines in the effective inhibiting of corrosion and rust formation. While considerable latitude is allowable in the selection of the soap, the soaps of the alkylolamines are to be avoided in view of their pronounced tendency toward the formation of foams. The alkylolamine soaps also do not permit ready settling of solid particles in the emulsion, such solid particles being the result of grindmetal sulfonates, such ing processes, etc. Therefore, there should be no acid in the composition available for the formation of soaps with the alkylolamines.
The mahogany sulfonates in the composition are the primary emulsifying agents, but emulsification is also promoted by the alkali metal soaps and the alkylolamines. Mahogany sulfonates, as is well known in the art, are the oil-soluble sulfonates formed in the sulfonation of petroleum oils. They are ordinarily prepared as alkali as sodium sulfonates, and they may be purified by several known methods. It is contemplated to use either the pure mahogany sulfonates or any of the commercial grades of varying degrees of purity. A commercial product containing about mahogany sulfonates has been found to be effective.
The petroleum oil in the soluble oil may be those commonly used in soluble oils, such as, for example, a petroleum lubricating oil having a viscosity of about '70 seconds at F. Saybolt Universal.
In preparing the soluble oil of this invention, a small amount of water is preferably used to make the soluble oil fluid and to prevent oil separation, or Stratification of the emulsion, upon mixing the soluble oil with larger amounts of water.
The proportions of the various ingredients in the soluble oil are quite flexible and may be varied over a, fairly Wide range, according to the particular properties desired in the finished product. However, to obtain the best results the proportions should be maintained within the following ranges:
Per cent by weight:
Mahogany sulfonates 5 to 15 Neutral alkali metal soap 2- to 6 Alkylolamine l. 0.5 to 4 Water 1 to 5 Petroleum oil Balance In the preparation of the soluble oil, rosin is dissolved in a portion'of the petroleum oil at a temperature of about 200 F. The mahogany soaps, which are readily soluble in this mixture,
are then added. To eiTect the saponification of the rosin, an aqueous solution of caustic soda is stirred into the mixture while maintaining the temperature at about 160 to 170 F. The proportion of alkali is carefully adjusted so that complete saponification occurs. Otherwise, a portion of the rosin would be available for the formation of soap with the alklolamine added at a later stage in the process. The presence of even small proportions of soaps of alklolamines is to be avoided in view of the fact that these soaps promote foaming and do not permit settling of solid particles in the emulsions formed from the soluble oils. After complete saponification of the rosin, the remainder of the petroleum oil and the required amount of alkylolamines are added. If necessary, the water content is then adjusted to obtain maximum stability, and the mixture is withdrawn as a finished product. The above procedure is given merely as an example of a suitable method of preparation, but obviously other methods will be apparent to those skilled in the art.
A soluble oil which is particularly efiective in grinding processes has the following composition:
Per cent by weight: Commercial mahogany sulfonates (containing about 65% mahogany sulfonates) 15.0 Sodium resinate 2.65 Triethanolamine 1.0 Water 2.0 Petroleum oil (lubricating oil; viscosity '70 seconds at 100 F., Saybolt Universal) Balance While this composition in the ordinary dilutions, for example, one part of the soluble oil diluted with ten parts of water, forms almost no rust, it can be further improved by the addition of small proportions of an alkali metal hydroxide. For example, the proportion of about 0.1% sodium hydroxide results in a composition which has no material effect on metals upon contact over extended periods of time. Therefore, it is preferred to add from 0.01 to 0.2% of an alkali metal hydroxide to any of the soluble oils prepared according to the invention wherever minimum corrosion and rusting of metals is desired. It is to be understood, how- 'ever, that the mere presence of an excess of an alkali metal hydroxide in any emulsion does not necessarily result in the prevention of rust formation. An emulsion containing no free alkylolamine is not improved with respect to rust prevention by the presence of excess caustic. Therefore, the improvement obtained when an excess of an alkali metal hydroxide is added in v the preparation of the composition of this in- When the use of very hard water is necessary, it is therefore desirable to increase the proportion of sodium resinate. For example, increasing the proportion of sodium resinate from 2.65% to 5.3% results in a completely stable emulsio where water of high hardness is used.
Wheneverit is necessary to increase the proportion of alkali metal soap in the soluble oil, the tendency for the separation of soap at low temperatures increases. Therefore, for the higher proportions of soap, say 4 to 6%, it is desirable to add small proportions of stabilizers such as, for example, the butyl ether of diethylene glycol (butyl carbitol). The addition of about 0.1 to 0.2% butyl carbitol to soluble oils containing 5.3% sodium resinate effectively prevents soap separation at low temperatures,
Obviously, many modifications and variations of the invention may be made without departing from the spirit and scope thereof, and therefore i only such limitations should be imposed as are indicated in the appended claims.
I claim:
1. A soluble oil comprising a petroleum oil, mahogany sulfonates, a water-soluble soap, an alkylolamine in amounts suflicient to impart antirusting properties, and an alkali metal hydroxide.
2. A soluble oil comprising a petroleum oil, mahogany sulfonates, a water-soluble soap, an alkylolamine in amounts suflicient to impart antirusting properties, an'alkali metal hydroxide, and water.
3. A soluble 011 comprising a petroleum oil, mahogany sulfonates, a rosin soap, triethanolamine in amounts suflicient to impart anti-rustin properties, and an alkali metal hydroxide.
4. A soluble oil comprising a petroleum oil, mahogany sulfonates, a rosin soap, triethanolamine in amounts sufficient to impart anti-rusting properties, an alkali metal hydroxide, and water.
5. A soluble 011 comprising a petroleum oil, a water-soluble soap, triethanolamine in amounts suilicient to impart anti-rusting properties, and an alkali metal hydroxide.
6. A soluble oil comprising a petroleum oil, 5 to 15% mahogany sulfonates, 2 to 6% watersoluble alkali metal soap, and 0.5 to 4% alkylolamine, the petroleum oil constituting substantially all of the remainder.
7. A soluble oil comprising a petroleum oil, 5 to 15% mahogany sulfonates, 2 to 6% neutral alkali metal rosin soap, and 0.5 to 4% triethanolamine, the petroleum oil constituting substantially all of the remainder.
8. A soluble oil comprising a petroleum oil, 5 to 15% mahogany sulfonates, 2 to 6% rosin soap, 0.5 to 4% triethanolamine, and 0.01 to 0.2% alkali metal hydroxide, the petroleum oil constituting substantially all of the remainder.
9. A soluble oil comprising a petroleum oil, 5 to 15% mahogany sulfonates, 2 to 6% rosin soap, 0.5 to 4% triethanolamine, 0.01 to 0.2% alkali metal hydroxide, and 1 to 5% water, the petroleum oil constituting substantially all of the remainder.
10. A soluble oil comprising a petroleum oil, about 15% commercial mahogany sulfonates, about 2.65% rosin soap, about 1% triethanolamine, about 2% water, and about'0.1% sodium hydroxide, the petroleum oil constituting substantially all of the remainder.
11. A soluble oil comprising a petroleum oil,
about 15% commercial mahogany sulfonates,
droxide, the petroleum oil constituting substantially all of the remainder.
12. A soluble oil according to claim 11 con taining from 0.1 to 0.2% butyl ether of diethylene glycol.
13. A soluble oil comprising petroleum oil, 5 to 15% mahogany sulfonate, 2 to 6% neutral alkali metal rosin soap; 0.5 to 4% alkylolamine, and 1 to 5% water, the petroleum oil constituting substantially all of the remainder.
14. A soluble oil comprising petroleumoil, 5 to 15% mahogany sulfonate, 2 to 6% alkali metal rosin soap, said soap being completely saponifled, 0.5 to 4% alkylolamine, and 1 to 5% water, the petroleum oil constituting substantially all of the remainder.
15. A soluble oil'comprising petroleum oil, mahogany sulfonate, water soluble soap, 0.5 to 4% alkylolamine, 0.01 to 0.2% alkali metal hydroxide, and water, the petroleum oil constituting substantially all of the remainder.
16.-A soluble oil as claimed in claim 15 in which the water soluble soap is a rosin soap.
17. A soluble oil comprising petroleum oil, mahogany sulfonate, 4 to 6% rosin soap, alkylolamine in amounts sufficient to impart anti-rusting properties, and a small amount of butyl ether of diethylene glycol, the petroleum oil constituting substantially all of the remainder.
THEODORE W. LANGER.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US351990A US2328727A (en) | 1940-08-09 | 1940-08-09 | Soluble oil |
Applications Claiming Priority (1)
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US351990A US2328727A (en) | 1940-08-09 | 1940-08-09 | Soluble oil |
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US2328727A true US2328727A (en) | 1943-09-07 |
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Cited By (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2421158A (en) * | 1942-05-20 | 1947-05-27 | Emery Industries Inc | Cutting oil base |
US2421159A (en) * | 1942-05-20 | 1947-05-27 | Emery Industries Inc | Cutting oil base |
US2423144A (en) * | 1944-10-07 | 1947-07-01 | Shell Dev | Emulsifiable hydrocarbon oils and emulsions thereof |
US2436046A (en) * | 1944-12-22 | 1948-02-17 | Standard Oil Co | Emulsifiable soluble oil compositions |
US2438461A (en) * | 1944-08-03 | 1948-03-23 | Standard Oil Dev Co | Cutting oil composition |
US2443833A (en) * | 1942-05-20 | 1948-06-22 | Emery Industries Inc | Cutting oil base |
US2563588A (en) * | 1951-08-07 | Soluble cutting oils | ||
US2614948A (en) * | 1947-03-27 | 1952-10-21 | Michael W Freeman | Producing modified machine elements |
US2626240A (en) * | 1949-06-25 | 1953-01-20 | Texas Co | Noncorrosive soluble oil containing active sulfur |
US2655478A (en) * | 1949-06-25 | 1953-10-13 | Texas Co | Noncorrosive soluble oil containing active sulfur |
US2665995A (en) * | 1950-05-26 | 1954-01-12 | Tide Water Associated Oil Comp | Rust inhibiting composition |
US2695272A (en) * | 1952-05-21 | 1954-11-23 | Standard Oil Dev Co | Soluble metalworking oil |
US2789071A (en) * | 1952-10-06 | 1957-04-16 | Michael W Freeman | Compositions and methods for treating articles |
DE1032871B (en) * | 1954-11-16 | 1958-06-26 | British Petroleum Co | Emulsion cylinder lubricant for internal combustion engines operated with residual fuels |
DE1038688B (en) * | 1956-06-08 | 1958-09-11 | Esso A G | Cylinder lubricant for the lubrication of large diesel engines operated with diesel or heating oils with a high sulfur content |
US2913410A (en) * | 1955-08-11 | 1959-11-17 | Gulf Oil Corp | Soluble oil |
US2992948A (en) * | 1958-11-24 | 1961-07-18 | Michael W Freeman | Metal coating composition and method of coating |
US3000826A (en) * | 1957-04-02 | 1961-09-19 | Texaco Inc | Transparent metal working lubricant composition |
US3006858A (en) * | 1958-01-02 | 1961-10-31 | Nalco Chemical Co | Method of improvement of heat transfer coefficient in heat exchangers |
US3028335A (en) * | 1958-10-20 | 1962-04-03 | Waverly Oil Works Company | Lubricating composition |
US3057799A (en) * | 1959-06-02 | 1962-10-09 | Sea Gull Lubricants Inc | Rust inhibiting soluble oil composition |
US3071544A (en) * | 1959-08-14 | 1963-01-01 | Sun Oil Co | Emulsifiable mixtures of mineral oil and esters |
US3098821A (en) * | 1958-12-30 | 1963-07-23 | Sonneborn Chemical And Refinin | Cutting oil preparation |
US3259578A (en) * | 1960-08-04 | 1966-07-05 | Petrolite Corp | Lubricating compositions |
DE1242782B (en) * | 1956-02-16 | 1967-06-22 | Labofina Sa | Lubricants for heat engines |
US4134415A (en) * | 1976-03-08 | 1979-01-16 | Texaco Inc. | Pipeline transportation of heavy crude oil |
US4192767A (en) * | 1976-03-08 | 1980-03-11 | Texaco Inc. | Aqueous surfactant solutions and oil-in-water emulsions |
US4273664A (en) * | 1978-06-02 | 1981-06-16 | Snamprogetti S.P.A. | Rust-preventing agent for aqueous systems and rust-inhibiting lubricating compositions |
-
1940
- 1940-08-09 US US351990A patent/US2328727A/en not_active Expired - Lifetime
Cited By (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2563588A (en) * | 1951-08-07 | Soluble cutting oils | ||
US2421158A (en) * | 1942-05-20 | 1947-05-27 | Emery Industries Inc | Cutting oil base |
US2421159A (en) * | 1942-05-20 | 1947-05-27 | Emery Industries Inc | Cutting oil base |
US2443833A (en) * | 1942-05-20 | 1948-06-22 | Emery Industries Inc | Cutting oil base |
US2438461A (en) * | 1944-08-03 | 1948-03-23 | Standard Oil Dev Co | Cutting oil composition |
US2423144A (en) * | 1944-10-07 | 1947-07-01 | Shell Dev | Emulsifiable hydrocarbon oils and emulsions thereof |
US2436046A (en) * | 1944-12-22 | 1948-02-17 | Standard Oil Co | Emulsifiable soluble oil compositions |
US2614948A (en) * | 1947-03-27 | 1952-10-21 | Michael W Freeman | Producing modified machine elements |
US2626240A (en) * | 1949-06-25 | 1953-01-20 | Texas Co | Noncorrosive soluble oil containing active sulfur |
US2655478A (en) * | 1949-06-25 | 1953-10-13 | Texas Co | Noncorrosive soluble oil containing active sulfur |
US2665995A (en) * | 1950-05-26 | 1954-01-12 | Tide Water Associated Oil Comp | Rust inhibiting composition |
US2695272A (en) * | 1952-05-21 | 1954-11-23 | Standard Oil Dev Co | Soluble metalworking oil |
US2789071A (en) * | 1952-10-06 | 1957-04-16 | Michael W Freeman | Compositions and methods for treating articles |
DE1032871B (en) * | 1954-11-16 | 1958-06-26 | British Petroleum Co | Emulsion cylinder lubricant for internal combustion engines operated with residual fuels |
US2913410A (en) * | 1955-08-11 | 1959-11-17 | Gulf Oil Corp | Soluble oil |
DE1242782B (en) * | 1956-02-16 | 1967-06-22 | Labofina Sa | Lubricants for heat engines |
DE1038688B (en) * | 1956-06-08 | 1958-09-11 | Esso A G | Cylinder lubricant for the lubrication of large diesel engines operated with diesel or heating oils with a high sulfur content |
US3000826A (en) * | 1957-04-02 | 1961-09-19 | Texaco Inc | Transparent metal working lubricant composition |
US3006858A (en) * | 1958-01-02 | 1961-10-31 | Nalco Chemical Co | Method of improvement of heat transfer coefficient in heat exchangers |
US3028335A (en) * | 1958-10-20 | 1962-04-03 | Waverly Oil Works Company | Lubricating composition |
US2992948A (en) * | 1958-11-24 | 1961-07-18 | Michael W Freeman | Metal coating composition and method of coating |
US3098821A (en) * | 1958-12-30 | 1963-07-23 | Sonneborn Chemical And Refinin | Cutting oil preparation |
US3057799A (en) * | 1959-06-02 | 1962-10-09 | Sea Gull Lubricants Inc | Rust inhibiting soluble oil composition |
US3071544A (en) * | 1959-08-14 | 1963-01-01 | Sun Oil Co | Emulsifiable mixtures of mineral oil and esters |
US3259578A (en) * | 1960-08-04 | 1966-07-05 | Petrolite Corp | Lubricating compositions |
US4134415A (en) * | 1976-03-08 | 1979-01-16 | Texaco Inc. | Pipeline transportation of heavy crude oil |
US4192767A (en) * | 1976-03-08 | 1980-03-11 | Texaco Inc. | Aqueous surfactant solutions and oil-in-water emulsions |
US4273664A (en) * | 1978-06-02 | 1981-06-16 | Snamprogetti S.P.A. | Rust-preventing agent for aqueous systems and rust-inhibiting lubricating compositions |
US4388199A (en) * | 1978-06-02 | 1983-06-14 | Snamprogetti S.P.A. | Aqueous rust-inhibiting and lubricating compositions |
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