US3192163A - Process for the stabilization of petroleum lubricants - Google Patents

Process for the stabilization of petroleum lubricants Download PDF

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US3192163A
US3192163A US96676A US9667661A US3192163A US 3192163 A US3192163 A US 3192163A US 96676 A US96676 A US 96676A US 9667661 A US9667661 A US 9667661A US 3192163 A US3192163 A US 3192163A
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petroleum
lubricant
nitro
methyl
bis
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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
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic 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
    • C10M2203/108—Residual fractions, e.g. bright stocks
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/18—Natural waxes, e.g. ceresin, ozocerite, bees wax, carnauba; Degras
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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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    • C10M2207/10—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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    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/18—Tall oil acids
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • 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
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/10—Amides of carbonic or haloformic acids
    • C10M2215/102—Ureas; Semicarbazides; Allophanates
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
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    • C10M2215/26—Amines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/135—Steam engines or turbines
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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 nitroainines having the structural formula:
  • R is lower alkyl and hydrogen and where R is selected from the group consisting of the radical N(R the morpholino radical and the piperidyl radical and R is selected from the group consisting of lower alkyl, lower hydroxyl alkyl, and hydrogen.
  • nitroamines having the above structural formula are included 2-nitro-2-methyl-l,3-bis(dibutylamino)propane, 2-nitro-2-methyl-l,3-bis(Z-hydroxypropyl)aminopropane, 2-nitro-2-methyl-1,3-dimorpholinopropane, 2-nitro-2-methyl-l,3-dipiperidylpropane, and 2-mitro-2-ethyl-1,3-bis(dimethylamino)propane.
  • 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.
  • 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.
  • 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 bacterial inhibitors sold by Texaco Incorporated under the name of Soluble Oil Texaco-C.
  • To each of one-gallon containers was added '1 liter of watercutting oil emulsion. Desired amounts of my nitroamines were added to the cutting-oil emulsion in the first container. No inhibitor was added to the other container which was used as a control.
  • 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-week period, 5 mls. of bacterial culture were added at periodic weekly intervals.
  • I V To test the
  • Example II Coucentra- Number Nitroamine tion in :1 of days water-cutting effective oil emulsion 42 2-nitro-2'ethyl-l,3-bis(dimethylamino)propane. 250 1 -2 2-nitro-2-methyl-1,3-dirn0rph'ol1nopropane.. 2-nitro-2-methyl-1,3-dipiperidylpropane 1, 000 42 Control 0
  • Example II Example 111 The following is a stabilized steam cylinder oil which is adequately protected by 1,000 ppm. of 2-nitro-2-methyl-1,3-bis (dibutylamino) propane.
  • Example IV Percent by weight S.A.E. lubricating oil Oleic acid 10
  • Example IV The following is a core oil which is adequately protected by 1,000 ppm. of Z-nitro-Z-methyl-l,3-bis(2-hydroxypropyl) aminoprop ane.
  • Example V The following is a cutting oil which is adequately protected by 1,000 ppm. of 2-nitro-2-ethyl-1,3-bis(dimethylamino) propane.
  • a liquid petroleum lubricant composition consisting essentially of a liquid petroleum lubricant and a sufiicient amount of a nitroamine to stabilize said lubricant against metabolizing bacteria, said nitroamine having the structural formula:
  • R Ri-OHz( J-CHz-R1 wherein R is lower alkyl and hydrogen and wherein R is selected from the group consisting of the radical N (R the morpholino radical and the piperidyl radical and R is selected from the group consisting of lower alkyl, lower hydroxyl alkyl, and hydrogen.
  • a liquid'petroleum lubricant composition consisting essentially of a liquid petroleum lubricantand a sufficient amount of 2-nitro-2-ethyl1,3-bis(dimethylaminohprop ane to stabilize said lubricant against metabolizing bacteria.
  • a liquid petroleum lubricant composition consisting essentially of a liquid petroleum lubricant and a sufiicient amount Of 2-nitro-2-methyll ,3-bis dibutylainino propane to stabilize said lubricant against metabolizing bacteria.
  • a liquid petroleum lubricant composition consisting essentially of a liquid petroleum lubricant and a suflicient amount of 2 nitro 2 methyl-1,3-bis(2-hydroxypropyl) aminopropane to stabilize said lubricant against metabolizing bacteria.
  • a liquid petroleum lubricant composition consisting essentially of a liquid petroleum lubricant and a sufiicient amount of Z-nitro-Z-methyl-1,3-dipiperidylpropane to stabilize said lubricant against metabolizing bacteria.
  • An aqueous petroleum emulsion consisting essentially of an aqueous petroleum lubricant emulsion and a sutficient amount of a nitroainine to stabilize said lubricant against metabolizing bacteria, said nitroamine having the structural formula:
  • R is lower alkyl and hydrogen and wherein R is selected from the group consisting of the radial References Cited by the Examiner UNITED STATES PATENTS 2,381,408 8/45 Senkus 167-22 XR 2,474,791 6/ 49 Senkus 260-247 2,913,414 11/59 Hodge 25251.5 2,976,244 1 3/61 Bennett 252-51.5 2,987,479 6/61 Bennett .252-5l.5 3,054,748 9/62 Hodge l67 22 DANIEL E. WY MAN, Primary Examiner; JULIUS GREENWALD, ALPHONSO D. SULLIVAN,

Description

United States Patent .s,l92,163 PRGCESS FOR THE STABILIZATHON 0F TETROLEUM LUERTCANT 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. $6,676
=Claims. (Cl. 25249.5)
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 nitroainines having the structural formula:
where R is lower alkyl and hydrogen and where R is selected from the group consisting of the radical N(R the morpholino radical and the piperidyl radical and R is selected from the group consisting of lower alkyl, lower hydroxyl alkyl, and hydrogen.
It is well known that organisms from the groups consisting of Corynebacterium, Achromobacter, lseudomonas, Nocardia and Mycobacterium metabolize petroleum hydrocarbons and fatty acids and thereby produce undesirable oxidation products.
The petroleum industry has long been interested in the 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 2-nitro-2-methyl-l,3-bis(dibutylamino)propane, 2-nitro-2-methyl-l,3-bis(Z-hydroxypropyl)aminopropane, 2-nitro-2-methyl-1,3-dimorpholinopropane, 2-nitro-2-methyl-l,3-dipiperidylpropane, and 2-mitro-2-ethyl-1,3-bis(dimethylamino)propane. 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 bacterial inhibitors sold by Texaco Incorporated under the name of Soluble Oil Texaco-C. To each of one-gallon containers was added '1 liter of watercutting oil emulsion. Desired amounts of my nitroamines were added to the cutting-oil emulsion in the first container. No inhibitor was added to the 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-week period, 5 mls. of bacterial culture were added at periodic weekly intervals. I V
The following table sets out the results of the above tests and the number of days of bacterial inhibition when the described concentration of the desired nitroamines were incorporated into the cutting-oil emulsion.
Table I Coucentra- Number Nitroamine tion in :1 of days water-cutting effective oil emulsion 42 2-nitro-2'ethyl-l,3-bis(dimethylamino)propane. 250 1 -2 2-nitro-2-methyl-1,3-dirn0rph'ol1nopropane.. 2-nitro-2-methyl-1,3-dipiperidylpropane 1, 000 42 Control 0 Example II Example 111 The following is a stabilized steam cylinder oil which is adequately protected by 1,000 ppm. of 2-nitro-2-methyl-1,3-bis (dibutylamino) propane.
Percent by weight S.A.E. lubricating oil Oleic acid 10 Example IV The following is a core oil which is adequately protected by 1,000 ppm. of Z-nitro-Z-methyl-l,3-bis(2-hydroxypropyl) aminoprop ane.
Percent by weight Crude tall oil 25 Fuel oil 35 Tall oil ester (glycol or glycerol) 40 Example V The following is a cutting oil which is adequately protected by 1,000 ppm. of 2-nitro-2-ethyl-1,3-bis(dimethylamino) propane.
Percent by weight Tallow 65 Paratfin wax 29 Beeswax 1.3 Oxalic acid 1.3 Potassium citrate 1.3 Urea 0.4
Now having described my invention, what I claim is: 1. A liquid petroleum lubricant composition consisting essentially of a liquid petroleum lubricant and a sufiicient amount of a nitroamine to stabilize said lubricant against metabolizing bacteria, said nitroamine having the structural formula:
R Ri-OHz( J-CHz-R1 wherein R is lower alkyl and hydrogen and wherein R is selected from the group consisting of the radical N (R the morpholino radical and the piperidyl radical and R is selected from the group consisting of lower alkyl, lower hydroxyl alkyl, and hydrogen.
2. A liquid'petroleum lubricant composition consisting essentially of a liquid petroleum lubricantand a sufficient amount of 2-nitro-2-ethyl1,3-bis(dimethylaminohprop ane to stabilize said lubricant against metabolizing bacteria.
3. A liquid petroleum lubricant composition consisting essentially of a liquid petroleum lubricant and a sufiicient amount Of 2-nitro-2-methyll ,3-bis dibutylainino propane to stabilize said lubricant against metabolizing bacteria.
4. A liquid petroleum lubricant composition consisting essentially of a liquid petroleum lubricant and a suflicient amount 0f= 2-nitro-2-methyl-1,3-dimorpholinopr0pane to stabilize said lubricant against metabolizing bacteria.
A liquid petroleum lubricant composition consisting essentially of a liquid petroleum lubricant and a suflicient amount of 2 nitro 2 methyl-1,3-bis(2-hydroxypropyl) aminopropane to stabilize said lubricant against metabolizing bacteria.
6. A liquid petroleum lubricant composition consisting essentially of a liquid petroleum lubricant and a sufiicient amount of Z-nitro-Z-methyl-1,3-dipiperidylpropane to stabilize said lubricant against metabolizing bacteria.
'7. An aqueous petroleum emulsion consisting essentially of an aqueous petroleum lubricant emulsion and a sutficient amount of a nitroainine to stabilize said lubricant against metabolizing bacteria, said nitroamine having the structural formula:
wherein R is lower alkyl and hydrogen and wherein R is selected from the group consisting of the radial References Cited by the Examiner UNITED STATES PATENTS 2,381,408 8/45 Senkus 167-22 XR 2,474,791 6/ 49 Senkus 260-247 2,913,414 11/59 Hodge 25251.5 2,976,244 1 3/61 Bennett 252-51.5 2,987,479 6/61 Bennett .252-5l.5 3,054,748 9/62 Hodge l67 22 DANIEL E. WY MAN, Primary Examiner; JULIUS GREENWALD, ALPHONSO D. SULLIVAN,
Examiners.

Claims (1)

1. A LIQUID PETROLEUM LIBRICANT COMPOSITION CONSISTING ESSENTIALLY OF A LIQUID PETROLEUM LUBRICANT AND A SUFFICIENT AMOUNT OF A NITROAMINE TO STABILIZE SAID LUBRICANT AGAINST METABOLIZING BACTERIA, SAID NITROAMINE HAVING THE STRUCTUREAL FORMULA:
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US4101433A (en) * 1977-03-25 1978-07-18 Imc Chemical Group, Inc. Composition
US4390438A (en) * 1981-10-16 1983-06-28 Nalco Chemical Company Dibasic acids to reduce coefficient of friction in rolling oils
US4607036A (en) * 1983-12-15 1986-08-19 Lever Brothers Company Preservative compositions employing anti-microbial morpholine derivatives
JP2008081602A (en) * 2006-09-27 2008-04-10 Yushiro Chem Ind Co Ltd Water-soluble metal working agent, coolant and its preparation method, microorganism deterioration prevention method for water-soluble metal working agent and metal working

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US2381408A (en) * 1943-04-12 1945-08-07 Commerical Solvents Corp Nitro amines and process for preparing same
US2474791A (en) * 1945-02-26 1949-06-28 Commercial Solvents Corp Nitroalkyl substituted heterocyclic compounds and process for preparing them
US2913414A (en) * 1957-08-01 1959-11-17 Commercial Solvents Corp Petroleum lubricants stabilized against hydrocarbon metabolizable microor-ganisms
US2976244A (en) * 1958-06-27 1961-03-21 Commercial Solvents Corp Petroleum lubricants stabilized with nitroesters
US2987479A (en) * 1958-06-27 1961-06-06 Commercial Solvents Corp Stabilization of petroleum lubricants
US3054748A (en) * 1960-05-23 1962-09-18 Commercial Solvents Corp Process for the control of bacteria in water flooding operations in secondary oil recovery

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2381408A (en) * 1943-04-12 1945-08-07 Commerical Solvents Corp Nitro amines and process for preparing same
US2474791A (en) * 1945-02-26 1949-06-28 Commercial Solvents Corp Nitroalkyl substituted heterocyclic compounds and process for preparing them
US2913414A (en) * 1957-08-01 1959-11-17 Commercial Solvents Corp Petroleum lubricants stabilized against hydrocarbon metabolizable microor-ganisms
US2976244A (en) * 1958-06-27 1961-03-21 Commercial Solvents Corp Petroleum lubricants stabilized with nitroesters
US2987479A (en) * 1958-06-27 1961-06-06 Commercial Solvents Corp Stabilization of petroleum lubricants
US3054748A (en) * 1960-05-23 1962-09-18 Commercial Solvents Corp Process for the control of bacteria in water flooding operations in secondary oil recovery

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4101433A (en) * 1977-03-25 1978-07-18 Imc Chemical Group, Inc. Composition
US4390438A (en) * 1981-10-16 1983-06-28 Nalco Chemical Company Dibasic acids to reduce coefficient of friction in rolling oils
US4607036A (en) * 1983-12-15 1986-08-19 Lever Brothers Company Preservative compositions employing anti-microbial morpholine derivatives
JP2008081602A (en) * 2006-09-27 2008-04-10 Yushiro Chem Ind Co Ltd Water-soluble metal working agent, coolant and its preparation method, microorganism deterioration prevention method for water-soluble metal working agent and metal working
US20100093868A1 (en) * 2006-09-27 2010-04-15 Yushiro Chemical Industry Co., Ltd. Water-soluble metal-processing agent, coolant, method for preparation of the coolant, method for prevention of microbial deterioration of water-soluble metal-processing agent, and metal processing
CN101522875B (en) * 2006-09-27 2012-07-04 尤希路化学工业株式会社 Water-soluble metal-processing agent, coolant, method for preparation of the coolant, method for prevention of microbial deterioration of water-soluble metal-processing agent, and metal processing
US8476208B2 (en) 2006-09-27 2013-07-02 Yushiro Chemical Industry Co., Ltd. Water-soluble metal-processing agent, coolant, method for preparation of the coolant, method for prevention of microbial deterioration of water-soluble metal-processing agent, and metal processing

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