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US3183189A - Petroleum lubricants stabilized with bactericides - Google Patents

Petroleum lubricants stabilized with bactericides Download PDF

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Publication number
US3183189A
US3183189A US96695A US9669561A US3183189A US 3183189 A US3183189 A US 3183189A US 96695 A US96695 A US 96695A US 9669561 A US9669561 A US 9669561A US 3183189 A US3183189 A US 3183189A
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Prior art keywords
hydrocarbon
petroleum
liquid petroleum
nitrobutyl
stabilize
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US96695A
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Edward B Hodge
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Commercial Solvents Corp
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Commercial Solvents Corp
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
    • F16D—COUPLINGS FOR TRANSMITTING ROTATION; CLUTCHES; BRAKES
    • F16D3/00—Yielding couplings, i.e. with means permitting movement between the connected parts during the drive
    • F16D3/16—Universal joints in which flexibility is produced by means of pivots or sliding or rolling connecting parts
    • F16D3/20—Universal joints in which flexibility is produced by means of pivots or sliding or rolling connecting parts one coupling part entering a sleeve of the other coupling part and connected thereto by sliding or rolling members
    • F16D3/22—Universal joints in which flexibility is produced by means of pivots or sliding or rolling connecting parts one coupling part entering a sleeve of the other coupling part and connected thereto by sliding or rolling members the rolling members being balls, rollers, or the like, guided in grooves or sockets in both coupling parts
    • C—CHEMISTRY; METALLURGY
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
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    • C10M2203/106—Naphthenic fractions
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    • C10M2203/108—Residual fractions, e.g. bright stocks
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/124—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers thereof
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/286—Esters of polymerised unsaturated acids
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    • C10M2207/40—Fatty vegetable or animal oils
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/10—Amides of carbonic or haloformic acids
    • C10M2215/102—Ureas; Semicarbazides; Allophanates
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    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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    • C10M2215/26—Amines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling

Definitions

  • My invention relates to a stabilized petroleum lubricant and more particularly to a process for the production of stabilized petroleum lubricants containing as the active stabilizing agent nitroamines having the structural formula:
  • R is selected from the group consisting of lower alkyl and hydrogen; where R; is a member selected from v stabilization of various petroleum products such as cutting oils, hydraulic fluids, 'etc.,'against breakdown by bacteria which metabolize the hydrocarbons with the concurrent formation of deleterious metabolites.
  • nitroamines having the above structural formula are included N-(Z-nitroisbbutyl)diisopropylamine, N- Z-nitropropyl morpholine, N- 2-nitropropyl) dibutylamine, N (2 nitropropyl)diisobutylamine, N-(Z-nitrobutyl)dimethylamine, N -(2-nitrobutyl) 2 -'ethylhexylamine, N-(2-nitrobutyl)-l-amino-2-propanol, N-(Z-nitrobutyl)morpholine, N (2 nitrobutyl)piperidine, N (2- nitrobutyl)tetrahydrofurfurylamine, etc.
  • I have found that in some instances I can obtain total inhibition of bacterial growth in petroleum lubricants at concentrations as low as 100 ppm. I prefer to include at least 1,000 p.p.m. in most petroleum formulations. However, I can employ amounts up to about 2% by weight of the active nitroamines when the latter is soluble to this extent in the particular petroleum hydrocarbon composition.
  • EXAMPLE I To test the use of my active ingredients in cutting oils, a 25 :1 water-cutting oil emulsion was prepared.
  • the cutting oil concentrate used was a proprietary-cutting oil containing no bacteria inhibitors such as that sold by Texaco Incorporated under the name of Soluble Oil Texaco-C.
  • To each of one-gallon containers was added 1 liter of water-cutting oil emulsion. Desired amounts of my nitroamines were added to the cutting-oil emulsion in the first container. No inhibitor was added tothe other container which was used as a control. At the beginning of the experiment, each unit was inoculated with 5 mls.
  • Light mineral oil 90 Oleic acid l0 EXAMPLE III The following is a stabilized steam cylinder oil which is adequately protected by 1,000 p.p.m. of N-(2-nitrobutyl dimethylamine. r
  • a liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a sufiicient amount of N-(Z-nitroisobutyl)diisopropylamine to stabilize said hydrocarbon against metabolizing bacteria.
  • a liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a suflicicnt amount of N-(Z-nitropropyl)morpholine to stabilize said hydrocarbon against metabolizing bacteria.
  • a liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a sufiicicnt amount of N-(Z-nitropropyl)dibutylamine to stabilize said hydrocarbon against metabolizing bacteria.
  • A, liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a sufficient amount of N-(Z-nitropropyl)diisobutylamine to stabilize said hydrocarbon against metabolizing bacteria.
  • a liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a sufficient amount of N-(2-nitrobutyl)dimethylamine to stabilize said hydrocarbon against metabolizing bacteria.
  • a liquid petroleum composition consisting essen-.
  • a liquid petroleum composition consisting essen-.
  • a liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a suflicient amount of N-(Z-nitrobutyl)morpholine to stabilize said hydrocarbon against metabolizing bacteria.
  • a liquid petroleum composition consisting essentially of a liquidpetroleum lubricant hydrocarbon and a sufiicient amount of N-(2-nitrobutyl)piperidine to stabilize said hydrocarbon against metabolizing bacteria.
  • a liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a sulficient amount of N-(Z-nitrobutyl)tetrahydrofurfurylamine to stabilize said hydrocarbon against metabolizing bacteria.
  • An aqueous petroleum emulsion consisting essentially of an aqueous petroleum lubricant hydrocarbon emulsion and a sufiicient amount of a nitroamine to stabilize said hydrocarbon against metabolizing bacteria, said nitroamine having the structural formula:
  • R is selected from the group consisting of lower alkyl and hydrogen; where R is a member selected from the group consisting of -N(R morpholino, and piperidyl; and where R: is a member selected from the group consisting of hydrogen, tetrahydrofurfuryl, lower alkyl, and lower hydroxyalkyl.
  • a liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a sufiicient amount of'a nitroamine to stabilize said hydrocarbon against metabolizing bacteria, said nitroamine having the structural formula:
  • Rr-CHri -R where R is selected from the group consisting of lower alkyl and hydrogen; where R, is a member selected from the group consisting of N(R morpholino, piperidyl; and where R is a member selected from the group consisting of hydrogen, tetrahydrofurfuryl, lower alkyl and lower hydroxyalkyl.
  • composition of claim 13 wherein the composition contains from about p.p.m. to 2% by weight of the nitroamine.
  • composition of claim 11 wherein the composition contains from about 100 p.p.m. to 2% by weight of the nitroamine.
  • composition of claim 11 wherein the composition is a cutting oil.
  • composition of claim 11 wherein the composition is a steam cylinder oil.

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Description

United States Patent 3,183,189 PETROLEUM LUBRICANTS STABILIZED WITH BACTERICIDES Edward B. Hodge, Terre Haute, Ind., assignor to Commercial Solvents Corporation, New York, N.Y., a corporation of Maryland No Drawing. Filed Mar. 20, 1961, Ser. No. 96,695
16 Claims. (Cl. 252-495) My invention relates to a stabilized petroleum lubricant and more particularly to a process for the production of stabilized petroleum lubricants containing as the active stabilizing agent nitroamines having the structural formula:
where R is selected from the group consisting of lower alkyl and hydrogen; where R; is a member selected from v stabilization of various petroleum products such as cutting oils, hydraulic fluids, 'etc.,'against breakdown by bacteria which metabolize the hydrocarbons with the concurrent formation of deleterious metabolites.
Many compounds have been used as stabilization agents in lubricants, but very few have been found to be commercially successful due to the fact that the compounds are unstable, or are not active against a wide variety of microorganisms.
Among the nitroamines having the above structural formula are included N-(Z-nitroisbbutyl)diisopropylamine, N- Z-nitropropyl morpholine, N- 2-nitropropyl) dibutylamine, N (2 nitropropyl)diisobutylamine, N-(Z-nitrobutyl)dimethylamine, N -(2-nitrobutyl) 2 -'ethylhexylamine, N-(2-nitrobutyl)-l-amino-2-propanol, N-(Z-nitrobutyl)morpholine, N (2 nitrobutyl)piperidine, N (2- nitrobutyl)tetrahydrofurfurylamine, etc. I have found that in some instances I can obtain total inhibition of bacterial growth in petroleum lubricants at concentrations as low as 100 ppm. I prefer to include at least 1,000 p.p.m. in most petroleum formulations. However, I can employ amounts up to about 2% by weight of the active nitroamines when the latter is soluble to this extent in the particular petroleum hydrocarbon composition.
I have found that my active ingredients are effective bacteriostatic' agents in petroleum containing lubricants such as cutting oils, penetrating oils, grinding lubricants, iron tinning lubricants, core oils, hydraulic fluids, etc.
The following examples set out lubricating compositions in which my active ingredients act as effective bacteriostatic agents. It is not intended that my invention be limited to the compositions, portions, or lubricants set out below; but rather I intend for all equivalents and variations obvious to those skilled in the art to be included within the scope of this specification and the attached claims.
EXAMPLE I To test the use of my active ingredients in cutting oils, a 25 :1 water-cutting oil emulsion was prepared. The cutting oil concentrate used was a proprietary-cutting oil containing no bacteria inhibitors such as that sold by Texaco Incorporated under the name of Soluble Oil Texaco-C. To each of one-gallon containers was added 1 liter of water-cutting oil emulsion. Desired amounts of my nitroamines were added to the cutting-oil emulsion in the first container. No inhibitor was added tothe other container which was used as a control. At the beginning of the experiment, each unit was inoculated with 5 mls. of a heterogeneous bacterial culture which had grown for several years in a water-cutting oil emulsion. Aeration and mixing were obtained by using an air lift to continually circulate the mixture. The test was continued for a period of six weeks and during the six- 1 week period, 5 mls. of bacterial culture were added at periodic weekly intervals.
The following table sets out the results of the above tests and the number of days of bacterial irihibitionwhen the described concentration of the desired nitroamines were incorporated into the cutting-oil emulsion.
\ EXAMPLE II The following is a water emulsifiable cutting oil which is adequately protected by 1,000 p.p.m. of my nitroamine inhibitors:
Percent by weight Light mineral oil 90 Oleic acid l0 EXAMPLE III The following is a stabilized steam cylinder oil which is adequately protected by 1,000 p.p.m. of N-(2-nitrobutyl dimethylamine. r
Percent S.A.E. lubricating oil 90 Oleic'acid l0 EXAMPLE IV The following is a core oil which is adequately protected by 1,000 p.p.rn. of N-(2-nitrobutyl)morpholine.
Percent Crude tall oil 25 Fuel oil Tall oil ester (glycol or glycerol) 40 EXAMPLE v The following is a cutting oil which is adequately protected by 1,000 p.p.m. of N-(Z-nitrobutyl)piperidine.
Percent Tallow Paraffin wax 29 Beeswax 1.3 Oxalic acid 1.3 Potassium citrate 1.3 Urea 0.4
Patented May 11, I965 Now having described my invention, what I claim is:
l. A liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a sufiicient amount of N-(Z-nitroisobutyl)diisopropylamine to stabilize said hydrocarbon against metabolizing bacteria.
2. A liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a suflicicnt amount of N-(Z-nitropropyl)morpholine to stabilize said hydrocarbon against metabolizing bacteria.
3. A liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a sufiicicnt amount of N-(Z-nitropropyl)dibutylamine to stabilize said hydrocarbon against metabolizing bacteria.
4. A, liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a sufficient amount of N-(Z-nitropropyl)diisobutylamine to stabilize said hydrocarbon against metabolizing bacteria.
5. A liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a sufficient amount of N-(2-nitrobutyl)dimethylamine to stabilize said hydrocarbon against metabolizing bacteria.
6. A liquid petroleum composition consisting essen-.
tially of a liquid petroleum lubricant hydrocarbon and a sufiicient amount of N-(Z-nitrobutyl)-2-ethylhexylamine to stabilize said hydrocarbon against metabolizing bacteria.
7. A liquid petroleum composition consisting essen-.
tially of a liquid petroleum lubricant hydrocarbon and a sufficient amount of N-(Z-nitrobtityl)-1-amino-2-propanol to stabilize said hydrocarbon against metabolizing bacteria.
8. A liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a suflicient amount of N-(Z-nitrobutyl)morpholine to stabilize said hydrocarbon against metabolizing bacteria.
9. A liquid petroleum composition consisting essentially of a liquidpetroleum lubricant hydrocarbon anda sufiicient amount of N-(2-nitrobutyl)piperidine to stabilize said hydrocarbon against metabolizing bacteria.
10. A liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a sulficient amount of N-(Z-nitrobutyl)tetrahydrofurfurylamine to stabilize said hydrocarbon against metabolizing bacteria.
11. An aqueous petroleum emulsion consisting essentially of an aqueous petroleum lubricant hydrocarbon emulsion and a sufiicient amount of a nitroamine to stabilize said hydrocarbon against metabolizing bacteria, said nitroamine having the structural formula:
where R is selected from the group consisting of lower alkyl and hydrogen; where R is a member selected from the group consisting of -N(R morpholino, and piperidyl; and where R: is a member selected from the group consisting of hydrogen, tetrahydrofurfuryl, lower alkyl, and lower hydroxyalkyl.
12. A liquid petroleum composition consisting essentially of a liquid petroleum lubricant hydrocarbon and a sufiicient amount of'a nitroamine to stabilize said hydrocarbon against metabolizing bacteria, said nitroamine having the structural formula:
Rr-CHri -R where R is selected from the group consisting of lower alkyl and hydrogen; where R, is a member selected from the group consisting of N(R morpholino, piperidyl; and where R is a member selected from the group consisting of hydrogen, tetrahydrofurfuryl, lower alkyl and lower hydroxyalkyl.
13. The composition of claim 12 wherein the composition contains from about p.p.m. to 2% by weight of the nitroamine.
14. The composition of claim 11 wherein the composition contains from about 100 p.p.m. to 2% by weight of the nitroamine.
15. The-composition of claim 11 wherein the composition is a cutting oil.
16. The composition of claim 11 wherein the composition is a steam cylinder oil.
References Cited by the Examiner UNITED STATES PATENTS 2,419,506 4/47 Senkus 260-583 2,465,958 3/49 Senkus 260-347.7 2,474,791 6/49 Senkus 260-247 2,588,428 3/52 Stewart et a1. 167-22 2,812,332 11/57 Pennino 167-33 2,913,414 11/59 Hodge 252-515 3,054,749 9/62 Bennett et a1 252-8.55
FOREIGN PATENTS 107,419 5/39 Australia.
160,367 1/55 Australia.
421,189 3/47 Italy.
DANIEL E. WYMAN, Primary Examiner.
J ULIUS GREENWALD, Examiner.

Claims (1)

11. AN AQUEOUS PETROLEUM EMULSION CONSISTING ESSENTIALLY OF AN AQUEOUS PETROLEUM LUBICANT HYDROCARBON EMULSION AND A SUFICIENT AMOUNT OF A NITROAMINE TO STABILIZE SAID HYDROCARBON AGAINST METABOLIZING BACTERIA, SAID NITROAMINE HAVING THE STRUCTURAL FORMULA:
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990002782A1 (en) * 1988-09-06 1990-03-22 The Lubrizol Corporation Nitro-groups containing amines, and fuels compositions containing same
US4941986A (en) * 1989-03-16 1990-07-17 The Lubrizol Corporation Liquid compositions containing organic nitro compounds

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2419506A (en) * 1945-02-26 1947-04-22 Commercial Solvents Corp Alkyl and hydroxyalkyl nitro amines and process for preparing them
US2465958A (en) * 1947-03-14 1949-03-29 Commercial Solvents Corp Nitro amines and process for preparing them
US2474791A (en) * 1945-02-26 1949-06-28 Commercial Solvents Corp Nitroalkyl substituted heterocyclic compounds and process for preparing them
US2588428A (en) * 1945-04-02 1952-03-11 Goodrich Co B F Complex amine products with dialkyl zinc dithiocarbamates as pesticides
US2812332A (en) * 1955-04-01 1957-11-05 Goodrich Co B F Quaternary ammonium xanthates
US2913414A (en) * 1957-08-01 1959-11-17 Commercial Solvents Corp Petroleum lubricants stabilized against hydrocarbon metabolizable microor-ganisms
US3054749A (en) * 1960-06-10 1962-09-18 Commercial Solvents Corp Process for the control of bacteria in water flooding operations in secondary oil recovery

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2419506A (en) * 1945-02-26 1947-04-22 Commercial Solvents Corp Alkyl and hydroxyalkyl nitro amines and process for preparing them
US2474791A (en) * 1945-02-26 1949-06-28 Commercial Solvents Corp Nitroalkyl substituted heterocyclic compounds and process for preparing them
US2588428A (en) * 1945-04-02 1952-03-11 Goodrich Co B F Complex amine products with dialkyl zinc dithiocarbamates as pesticides
US2465958A (en) * 1947-03-14 1949-03-29 Commercial Solvents Corp Nitro amines and process for preparing them
US2812332A (en) * 1955-04-01 1957-11-05 Goodrich Co B F Quaternary ammonium xanthates
US2913414A (en) * 1957-08-01 1959-11-17 Commercial Solvents Corp Petroleum lubricants stabilized against hydrocarbon metabolizable microor-ganisms
US3054749A (en) * 1960-06-10 1962-09-18 Commercial Solvents Corp Process for the control of bacteria in water flooding operations in secondary oil recovery

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990002782A1 (en) * 1988-09-06 1990-03-22 The Lubrizol Corporation Nitro-groups containing amines, and fuels compositions containing same
US4941986A (en) * 1989-03-16 1990-07-17 The Lubrizol Corporation Liquid compositions containing organic nitro compounds

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