EP1153111A1 - Emulsion d'huile dans l'eau comprenant au moins un additif de lubrification - Google Patents

Emulsion d'huile dans l'eau comprenant au moins un additif de lubrification

Info

Publication number
EP1153111A1
EP1153111A1 EP00900673A EP00900673A EP1153111A1 EP 1153111 A1 EP1153111 A1 EP 1153111A1 EP 00900673 A EP00900673 A EP 00900673A EP 00900673 A EP00900673 A EP 00900673A EP 1153111 A1 EP1153111 A1 EP 1153111A1
Authority
EP
European Patent Office
Prior art keywords
additive
pss
emulsion
lubrication
coo
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.)
Withdrawn
Application number
EP00900673A
Other languages
German (de)
English (en)
French (fr)
Inventor
Hervé Derule
Hubert Jacobs
Amadou Dicko
Peggy Guinet
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
USINOR SA
Original Assignee
USINOR SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by USINOR SA filed Critical USINOR SA
Publication of EP1153111A1 publication Critical patent/EP1153111A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C10M173/00—Lubricating compositions containing more than 10% water
    • 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
    • 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
    • C10M137/105—Thio derivatives not containing metal
    • 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
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/047—Thioderivatives not containing metallic elements
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/241—Manufacturing joint-less pipes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/242—Hot working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/243—Cold working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/245—Soft metals, e.g. aluminum
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/246—Iron or steel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/247—Stainless steel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01—Emulsions, colloids, or micelles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/015—Dispersions of solid lubricants
    • C10N2050/02—Dispersions of solid lubricants dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating

Definitions

  • Oil-in-water emulsion comprising at least one lubrication additive.
  • the invention relates to an additive for soluble oil intended to reinforce the lubricating power of this oil, in particular when it is applied in a thin and "dry" film to a steel surface.
  • This oiling treatment is intended to ensure good lubrication between the sheet surface and that of the tools under the shaping conditions. Applied on bare steel sheets, this oiling treatment often has another temporary protection function against corrosion, as described in patent EP 0 577 486 from the company SOLLAC.
  • soluble that is to say emulsifiable in water, applied as an emulsion, the emulsion having at least two different phases, an aqueous liquid phase and an oily phase dispersed in the aqueous phase.
  • soluble oils make it easier to obtain homogeneous deposits which are very thin or of very low surface density, for example less than or equal to 1 g / m 2 .
  • soluble oils can be easily applied by spraying, which ensures a homogeneous deposit of very small thickness on the surface to be treated.
  • Patent EP 0 577 486 already cited describes a method of surface treatment of a metal part using an oil emulsion; according to the invention object of this patent, this treatment is suitable for forming, on this surface, a homogeneous and protective film, of dry, thin appearance and of surface density less than 1 g / m 2 .
  • the object of the invention is to propose an additive to increase the lubricating power of soluble oils when they are applied to bare steel surfaces, in particular when they are applied in thin and dry film to these surfaces.
  • the subject of the invention is an oil in water emulsion intended for a lubrication treatment of a steel surface comprising at least one lubrication additive chosen from the group comprising the products corresponding to the following formulas : - (R 1 2 -O-) 1 2 -PSS- (CH 2 ) n -COO- (CH 2 ) m -CH 3 with n and m chosen so that n + m> 22,
  • the invention may also have one or more of the following characteristics:
  • the proportion of lubrication additive in the oily phase of the emulsion is between 2% and 6%.
  • a subject of the invention is also a method for treating the lubrication of a steel surface comprising the steps of applying this emulsion to this surface followed by drying suitable for forming a dry film on said surface, the dry film having preferably a surface density less than or equal to 1 g / m 2 .
  • the invention also has the use of this treatment method for lubricating steel sheets before shaping, since the oiled sheets of dry appearance obtained by this treatment process require no re-oiling before shaping, in particular by stamping.
  • the lubrication treatment according to the invention is carried out on a sheet intended for enamelling or for painting, the invention advantageously makes it possible to avoid any degreasing operation after this lubrication and before this enamelling or painting at strictly speaking, in particular if the dry film which results from this treatment has a surface density less than or equal to 1 g / m 2 and even if a shaping operation is interposed between the lubrication and remeshing treatment or the painting.
  • the components necessary to prepare the emulsion are: the oil (s), the emulsifier (s) to form and maintain the emulsion, and, according to the invention, at least one lubrication additive corresponding to the formula:
  • additives can be added to the “oily base” or to the emulsion, such as corrosion inhibitors, film-forming agents, anti-foaming agents, bactericidal agents, or the like; these additives are known in themselves and will not be described here in detail.
  • the proportions of lubrication additive to be added to the oily base are preferably between 2% and 6% approximately; at 2%, a significant effect is observed but most of the tests were carried out at 5%.
  • the various fat-soluble components of the oily base are first mixed, including the lubrication additives according to the invention, and the oily base obtained is then emulsified by adding water under strong agitation; the proportion of water or the proportion (aqueous phase) / (oily phase) is adapted in a conventional manner.
  • the proportion of water or the proportion (aqueous phase) / (oily phase) is adapted in a conventional manner.
  • the steel surface to be treated is a sheet surface intended for shaping, for example by stamping.
  • a uniform emulsion layer is therefore applied in a conventional manner to the sheet, for example by spraying or by dipping, then the applied layer is dried, for example by blowing hot air, so as to obtain a uniform film and dry on the steel surface of the sheet; this application method followed by drying is described in particular in patent EP 0 577 486 already cited.
  • the drying is adapted to remove almost all of the water from the applied emulsion layer; drying is not too thorough to avoid any risk of degradation of the components of the oily base.
  • a steel sheet is thus obtained treated according to the invention, that is to say coated with an oil-based film comprising the lubrication additive according to the invention.
  • the lubrication additive according to the invention is compatible with the components of the oily bases suitable for temporary protection against corrosion, in particular the corrosion inhibiting agents.
  • AQUASAFE 21 an oil of the soluble type, called AQUASAFE 21, from the company CASTROL, generally used for the temporary protection against corrosion of steel parts.
  • V14 one to serve as a reference without any other additive, called V14 from the company FUCHS, generally used to treat steel parts both against corrosion and for lubrication before stamping;
  • the additive according to the invention is mixed with the AQUASAFE 21 oily base, then the oily mixture is emulsified with stirring;
  • the lubricant treatment product is prepared by mixing the additive according to the invention in the oily base, here SHELL 3282.
  • the sheet used for the lubrication treatment tests is a bare steel sheet 0.7 mm thick, taken directly from a continuous production line immediately downstream from a so-called “skinpass” operation. in the English language, carried out dry, without oil; this sheet, the surface of which is moreover not greasy, is not degreased.
  • stamping press adapted to produce buckets with an inside diameter of 50 mm from sheet blanks with a diameter of 90 mm; using a 50 mm diameter punch having at the end a radius of curvature of 3 mm, a 52.6 mm diameter die having an inner rim of radius of curvature 3.5 mm.
  • the drawing speed is set at 30 cm / min. ; the maximum force of hold-down is 150 kN.
  • the press is equipped with means for continuously monitoring the drawing parameters, in particular the blank holding pressure, the drawing force and the stroke of the punch.
  • the curve of the drawing force is plotted as a function of the stroke of the punch; this curve passes through a maximum which defines the maximum drawing force during operation.
  • This drawing test protocol therefore makes it possible to assess the level of lubrication of the surface of a sheet for drawing; to assess this level on one side, a film of Teflon ® (punch side) is affixed to the other side so as to obtain on this other side a friction which is always negligible compared to that which is exerted on the surface to be evaluated .
  • this protocol is applied directly to sheets treated according to the invention, without posterior oiling.
  • the additive used here according to the invention is O, O-di-isopropyl-dithiophosphate of 4-hydroxy-benzyl unsubstituted, of general formula (R 1) 2 -O-) 1> 2 -PSS- CH2- ⁇ -OH, where the radicals R j and R 2 are isopropyl.
  • the radical -OH is in the "para" position relative to the radical -CH2-S- on the aromatic ring ⁇ of the benzyl radical.
  • - Document EP 592 956 (LUBRIZOL) describes a lubricating composition (whole or soluble) containing oil, an additive resulting from the reaction between a dimercaptothiadiazole and an aliphatic olefin, and, according to claim 5, 0.1-1 % to 5-7% of a metal dithiophosphate as an extreme pressure agent (page 2, line 23 - pages 12-13);
  • Example 5 specifically describes the use, as an extreme pressure additive, of zinc isopropyl methylamyl dithiophosphate.
  • Tests are carried out both on samples treated with a freshly prepared additive emulsion and on samples treated with an "aged" additive emulsion in the sense that it was prepared three weeks before its application.
  • the following series of samples are thus prepared, under the conditions indicated in the MATERIALS section:
  • the stamping tests are carried out under the conditions indicated in ⁇ METHODS and the results obtained are plotted in a diagram comprising, on the abscissa, the clamping force of the blank holder (“FSF” in kN), and, on the ordinate, the maximum drawing force (“F.max” in kN); the diagram obtained is shown in FIG. 1.
  • the friction behavior of the samples ⁇ (without additive) reflects problems of grazing, which disappear completely on the samples ⁇ treated according to the invention.
  • the addition of soluble oils according to the invention therefore makes it possible to improve the friction behavior of bare steel sheets.
  • the first layer serving as a hanging base for the second layer - which is the one that gives the final appearance, with a single firing.
  • Additive OO-dialkyl-dithiophosphates of hvdroxybenzyle incidence of a polar group on the aromatic nucleus.
  • the purpose of this example is to illustrate the advantage of using O, O-dialkyl-dithiophosphates of hydroxybenzyl which are not unsubstituted by polar groups. Samples are treated with freshly prepared emulsions and tested under the conditions of Example 1.
  • - M denotes the additive O, O-di-isopropyl-dithiophosphate of 3-oxoethane-4-hydroxy-benzyie, denotes the additive O, O-di-isopropyl-dithiophosphate of 4-carboxy-benzyl, the term "Carboxy" designating the radical -COOH.
  • Additive according to the invention O, O-di-isopropyl-dithiophosphate of 4-hydroxy-benzyl, at 6 g / l of oily base.
  • Sheet used steel sheet coated by electrodeposition in a chloride medium with a layer of zinc with a thickness of the order of 10 ⁇ m.
  • the results of the stampability tests, carried out and presented as in Example 1, are reported in Figures 3 and 4:
  • IPr-O- 2 -PSS- (CH 2 ) 12 -COO- (CH 2 ) 10 -CH 3
  • IPr denotes the isopropyl group.
  • METHODS and the results obtained are plotted in a diagram comprising, on the abscissa, the clamping force of the blank holder (kN), and, on the ordinate, the maximum drawing force (kN); the diagram obtained is shown in FIG. 5.
  • the additive 1 deteriorates the lubricating properties of the Aquasafe oil 21, that the additive 2 does not modify them, while the additive 3 appreciably improves them.
  • Example 8 Effect of type of additives (R, -O) n-CH-PSS 9 - ⁇ -O- (CHo) n-COO-.
  • halide of the formula X-PSS- CH 2 - ⁇ -O- (CH 2 ) n -COO- (CH 2 ) m -CH 3 is synthesized, where X denotes bromine, by radical substitution of aromatic methylenes by N-bromosuccinimide in a solution of carbon tetrachloride in the presence of a catalyst of formula AIBN as initiator of free radicals;
  • Additives 1 ', 2' and 3 ' are then obtained by substitution of the para-substituted benzyl bromides on potassium O, O'-diisopropyl dithiphosphate in an ethanolic medium.
  • METHODS and the results obtained are plotted in a diagram comprising, on the abscissa, the clamping force of the blank holder (kN), and, on the ordinate, the maximum drawing force (kN); the diagram obtained is shown in FIG. 6.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
EP00900673A 1999-01-28 2000-01-28 Emulsion d'huile dans l'eau comprenant au moins un additif de lubrification Withdrawn EP1153111A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9900926A FR2789084B1 (fr) 1999-01-28 1999-01-28 Emulsion d'huile dans l'eau comprenant au moins un additif de lubrification
FR9900926 1999-01-28
PCT/FR2000/000187 WO2000044861A1 (fr) 1999-01-28 2000-01-28 Emulsion d'huile dans l'eau comprenant au moins un additif de lubrification

Publications (1)

Publication Number Publication Date
EP1153111A1 true EP1153111A1 (fr) 2001-11-14

Family

ID=9541302

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00900673A Withdrawn EP1153111A1 (fr) 1999-01-28 2000-01-28 Emulsion d'huile dans l'eau comprenant au moins un additif de lubrification

Country Status (8)

Country Link
US (1) US6486102B1 (pt)
EP (1) EP1153111A1 (pt)
JP (1) JP2002537413A (pt)
KR (1) KR20010111489A (pt)
BR (1) BR0007831A (pt)
CA (1) CA2360016A1 (pt)
FR (1) FR2789084B1 (pt)
WO (1) WO2000044861A1 (pt)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007061109B4 (de) 2007-12-19 2013-01-17 Henkel Ag & Co. Kgaa Behandlungslösung zum Beschichten eines Stahlbandes, ein Verfahren zum Aufbringen derselben sowie ein Stahlband mit einer Beschichtung erhalten aus der Behandlungslösung zur Verbesserung des Umformverhaltens
WO2013160566A1 (fr) 2012-04-25 2013-10-31 Arcelormittal Investigacion Y Desarrollo, S.L. Procédé de réalisation d'une tôle à revêtements znalmg huilés et tôle correspondante.
CN115521825B (zh) * 2022-11-07 2023-11-21 季华实验室 一种水基冲压液及其制备方法和应用
CN116554954B (zh) * 2023-05-11 2024-05-28 铜陵兢强电子科技股份有限公司 一种环保型漆包线表面润滑油及其制备方法

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US2530339A (en) * 1946-12-24 1950-11-14 Standard Oil Dev Co Compounded petroleum hydrocarbon products
US3350348A (en) * 1965-04-05 1967-10-31 Mobil Oil Corp Lubricating oil additives
US3567638A (en) * 1968-09-26 1971-03-02 Mobil Oil Corp Novel phosphorus-containing adducts in oil compositions containing the same
US3745148A (en) * 1971-04-05 1973-07-10 Ethyl Corp Stabilized organic compositions
US3865906A (en) * 1971-04-05 1975-02-11 Ethyl Corp 0,0-Dialkyl-(3,5-dialkyl-4-hydroxybenzyl)dithiophosphate compositions and process for making same
GB1569730A (en) * 1978-05-30 1980-06-18 Ciba Geigy Ag 0,0-diiso-propyl-s-(2-carboethoxyethyl)-phosphorodithioate and lubricating oil compositions containing it
US4333841A (en) * 1978-10-19 1982-06-08 Ciba-Geigy Corporation Dithiophosphate lubricant additives
DE3063981D1 (en) * 1979-09-18 1983-08-04 Ciba Geigy Ag Dithiophosphates, their preparation and lubricants containing them
TW279839B (pt) * 1992-06-02 1996-07-01 Ciba Geigy Ag
FR2692912B1 (fr) * 1992-06-30 1995-06-30 Lorraine Laminage Procede de protection contre la corrosion de pieces metalliques et pieces metalliques obtenues par ce procede.
EP0667389B1 (en) * 1994-02-11 2000-12-27 The Lubrizol Corporation Metal free hydraulic fluid with amine salt
SG84506A1 (en) * 1996-07-15 2001-11-20 Ciba Sc Holding Ag Beta-dithiophosphorylated propionic acid in lubricants
US5968880A (en) * 1997-10-23 1999-10-19 The Lubrizol Corporation Lubricating compositions, functional fluids and greases containing thiophosphorus esters or their salts with a oxyalkylene group, and methods of using the same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0044861A1 *

Also Published As

Publication number Publication date
KR20010111489A (ko) 2001-12-19
US6486102B1 (en) 2002-11-26
JP2002537413A (ja) 2002-11-05
FR2789084B1 (fr) 2001-03-09
WO2000044861A1 (fr) 2000-08-03
CA2360016A1 (fr) 2000-08-03
FR2789084A1 (fr) 2000-08-04
BR0007831A (pt) 2002-01-15

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