EP0200001B1 - Procédé pour revêtir une surface métallique d'huile lubrifiante - Google Patents

Procédé pour revêtir une surface métallique d'huile lubrifiante Download PDF

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Publication number
EP0200001B1
EP0200001B1 EP86104328A EP86104328A EP0200001B1 EP 0200001 B1 EP0200001 B1 EP 0200001B1 EP 86104328 A EP86104328 A EP 86104328A EP 86104328 A EP86104328 A EP 86104328A EP 0200001 B1 EP0200001 B1 EP 0200001B1
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EP
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Prior art keywords
lubricating oil
metal surface
coating
acid
reaction product
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Expired
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EP86104328A
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German (de)
English (en)
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EP0200001A1 (fr
Inventor
Yoshio Nagae
Takashi Nihon Parkerizing Ichikawa Kawakami
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Nihon Parkerizing Co Ltd
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Nihon Parkerizing Co Ltd
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Priority to AT86104328T priority Critical patent/ATE43650T1/de
Publication of EP0200001A1 publication Critical patent/EP0200001A1/fr
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M111/00Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/02Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a non-macromolecular organic compound
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32Esters
    • C10M105/40Esters containing free hydroxy or carboxyl groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/56Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
    • C10M105/58Amines, e.g. polyalkylene polyamines, quaternary amines
    • CCHEMISTRY; METALLURGY
    • C23COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23FNON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/281Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/282Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/283Esters of polyhydroxy compounds
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/286Esters of polymerised unsaturated acids
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/287Partial esters
    • C10M2207/2875Partial esters used as base material
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/287Partial esters
    • C10M2207/288Partial esters containing free carboxyl groups
    • C10M2207/2885Partial esters containing free carboxyl groups used as base material
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/287Partial esters
    • C10M2207/289Partial esters containing free hydroxy groups
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/287Partial esters
    • C10M2207/289Partial esters containing free hydroxy groups
    • C10M2207/2895Partial esters containing free hydroxy groups used as base material
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
    • C10M2207/404Fatty vegetable or animal oils obtained from genetically modified species
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/023Amines, e.g. polyalkylene polyamines; Quaternary amines used as base material
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/044Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08Amides
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26Amines
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    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives

Definitions

  • the invention relates to a method for coating a metal surface with a lubricating oil containing citric acid ester and its application to the coating of metal surfaces made of ferrous materials.
  • Metal sheets e.g. B. steel sheets or sheets of tinned steel, treated for the production of cans or similar containers with a corrosion-protecting lubricating oil, in order to prevent the formation of corrosion or abrasion during transport and storage.
  • a corrosion-protecting lubricating oil In view of the paintability or the removability of the lubricating oil with any cleaning agents, however, the layers produced must be extremely thin. With increasing shipping or export of sheets, the importance of such lubricating oils has increased significantly.
  • dioctyl sebazate has hitherto been applied to the metal sheets and then packaged with an anti-corrosive paper containing a volatile corrosion inhibitor.
  • the corrosion protection obtained in this way is unsatisfactory. It is also difficult to remove these oils, so that insufficient paint adhesion or uneven metal deposition can occur in the subsequent treatment.
  • the object of the invention is to provide a method for coating metal surfaces with lubricating oil which does not have the known, in particular the aforementioned disadvantages, and leads to treated metal surfaces which have superior results with regard to corrosion resistance, lubricity, paintability and printability as well as cleaning.
  • the object is achieved by designing the method of the type mentioned at the outset in accordance with the invention such that a lubricating oil which, in addition to citric acid ester, contains 5 to 40% by weight of a reaction product of organic carboxylic acid and amine, in an amount of Applying 4 to 250 mg / m 2 by electrostatic coating.
  • the content of the reaction product is given as a proportion of the lubricating oil.
  • a preferred embodiment of the invention is to apply a lubricating oil whose citric acid ester has the formula has, where R "R 2 and R 3 are hydrocarbon radicals having 1 to 8 carbon atoms.
  • the removability of the lubricating oil decreases with higher carbon chains.
  • citric acid esters are trimethyl citrate, triethyl citrate, tripropyl citrate, tributyl citrate and trioctyl citrate.
  • the corrosion protection achieved is unsatisfactory and the electrical conductivity of the lubricating oil increases, with the result that the film is more difficult to apply. If the hydrocarbon residue has 19 or more carbon atoms, the removability of the lubricating oil is reduced.
  • the carboxylic acids used can be both aliphatic and aromatic in nature.
  • propionic acid, butyric acid, caproic acid, caprylic acid, capric acid, lauric acid, oleic acid, benzoic acid, toluic acid, p-nitrobenzoic acid and tert-butylbenzoic acid are suitable.
  • Corrosion protection, removability, odor and electrical conductivity are particularly preferred caprylic acid, capric acid, lauric acid and benzoic acid.
  • a further advantageous embodiment of the invention therefore provides for the application of a lubricating oil, the reaction product of which is formed from a secondary or tertiary amine.
  • a lubricating oil the reaction product of which is formed from a secondary or tertiary amine.
  • Such amines are di- or trialkylamine, such as di- or tri-methylamine, -ethylamine, -butylamine, and also ethylhexylamine, but also amino alcohols, such as dimethylethanolamine, diethylethanolamine, dibutylethanolamine, dihexylethanolamine and the like.
  • cyclohexylamines such as dicyclohexylamine, and also morphine , Diethanolamine and methylmorpholine can be used.
  • the molar ratio of organic carboxylic acid to amine is preferably 1: 1.
  • the lubricating oil to be used in the process according to the invention can contain further additives which are conventional per se, such as animal or vegetable oil or synthetic esters, e.g. B. dioctyl sebazate, or acetylated trialkyl citrate, to adjust viscosity and conductivity.
  • Surfactants can be introduced to improve the removability of the lubricating oil.
  • the method according to the invention is suitable for coating a large number of metal surfaces. It is particularly applicable to the coating of sheet metal or strip made of steel or tinned steel.
  • a particularly suitable steel quality is so-called "tin-free steel", under which steel with combination layers of metallic chromium (e.g. 0.02 to 0.05 g / m 2 ) and chromium hydroxide (e.g. 0 , 2 to 0.5 g / m 2 , calculated as Cr (OH) 3. 3 H 2 0). These layers are produced by cathodic switching from electrolytes containing chromic acid and sulfuric acid or hydrogen fluoride.
  • Corrosion resistance 5 test sheets measuring 75 x 150 mm were coated with tarpaulin paper and wound into a package and sealed at the ends with adhesive tape. The package was then placed in the tester maintained at 50 ° C and 90% relative humidity for 20 days.
  • Lubricating oil removability Test sheets were placed in a 2% by weight sodium hydroxide solution at 80 ° C. and rinsed with water. The time until complete wettability with water is determined (the shorter the time, the better the removability).
  • Paint adhesion The sheets are coated with an epoxy phenol paint for cans in such a way that a layer weight of 50 ⁇ 5 mg / dm 2 results after the paint has hardened. The curing takes place at 200 to 205 ° C for a period of 10 minutes. The sheets are then cross-cut to the metal surface, so that squares of 1 mm 2 in size are produced. The degree of flaking is then determined and evaluated.
  • the lubricating oil was applied electrostatically to black plate by means of a coating device, so that a uniform layer weight of 25 mg / m 2 resulted.
  • the sheet treated in this way was then cut to 70 mm x 150 mm sections and subjected to the tests for lubricity, corrosion resistance, lubricant oil removability and paintability. The results of the test can be found in the final table.
  • the lubricating oil was examined in accordance with the information in Example 1. The results are also in the final table.
  • the lubricating oil was applied and tested under the conditions of Example 1. The results can be found in the final table.
  • Dioctyl sebazate with an electrical conductivity of 0.02 ⁇ S / cm was applied and tested under the conditions of Example 1.
  • Triethyl citrate with an electrical conductivity of 0.08 ⁇ S / cm was again applied and investigated under the conditions of Example 1.
  • the dibutylamine salt of caprylic acid was carried out as in Example 1, applied electrostatically and tested.

Claims (6)

1. Procédé pour le revêtement d'une surface métallique avec un huile lubrifiante contenant un ester d'acide citrique, caractérisé en ce que l'on applique par dépôt électrostatique sur la surface métallique, en une quantité de 4 à 250 mg/m2, une huile lubrifiante qui contient, en plus d'un ester d'acide citrique, de 5 à 40 % en poids d'un produit de réaction obtenu à partir d'un acide organique carboxylique et d'une amine.
2. Procédé selon la revendication 1, caractérisé en ce que l'on applique sur la surface métallique une huile lubrifiante dont l'ester d'acide citrique possède la formule
Figure imgb0012
dans laquelle R" R2 et R3 représentent des radicaux hydrocarbonés ayant de 1 à 8 atomes de carbone.
3. Procédé selon la revendication 1 ou 2, caractérisé en ce que l'on applique sur la surface métallique une huile lubrifiante dont le produit de réaction est formé à partir d'un acide carboxylique de formule
Figure imgb0013
dans laquelle R est un radical hydrocarboné ayant de 3 à 18 atomes de carbone:
4. Procédé selon la revendication 1, 2 ou 3, caractérisé en ce que l'on applique sur la surface métallique une huile lubrifiante dont le produit de réaction est formé a partir d'une amine secondaire ou tertiaire.
5. Procédé selon la revendication 1, 2, 3 ou 4, caractérisé en ce que l'on applique sur la surface métallique une huile lubrifiante dont le produit de réaction est formé à partir d'une amine qui comporte au maximum 2 groupes OH.
6. Utilisation du procédé selon une ou plusieurs des revendications 1 à 5, pour le revêtement de surfaces métalliques à base de matériaux ferreux, par exemple à base d'acier.
EP86104328A 1985-04-04 1986-03-28 Procédé pour revêtir une surface métallique d'huile lubrifiante Expired EP0200001B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT86104328T ATE43650T1 (de) 1985-04-04 1986-03-28 Verfahren zum beschichten einer metalloberflaeche mit schmieroel.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP70090/85 1985-04-04
JP60070090A JPS61230772A (ja) 1985-04-04 1985-04-04 金属の被覆法

Publications (2)

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EP0200001A1 EP0200001A1 (fr) 1986-11-05
EP0200001B1 true EP0200001B1 (fr) 1989-05-31

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EP86104328A Expired EP0200001B1 (fr) 1985-04-04 1986-03-28 Procédé pour revêtir une surface métallique d'huile lubrifiante

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EP (1) EP0200001B1 (fr)
JP (1) JPS61230772A (fr)
AT (1) ATE43650T1 (fr)
DE (2) DE3663691D1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7696136B2 (en) 2004-03-11 2010-04-13 Crompton Corporation Lubricant compositions containing hydroxy carboxylic acid and hydroxy polycarboxylic acid esters

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4209502A1 (de) * 1992-03-24 1993-09-30 Hoechst Ag Verwendung von Estern der Citronensäure als Schmiermittel für Kältemittelverdichter
DE4313752A1 (de) * 1993-04-27 1994-11-03 Karl Naumann Gmbh Verfahren zur formgebenden Bearbeitung von Metallteilen mit anschließender Lackierung
GB2296714B (en) * 1994-12-15 1998-03-25 Abbey Coating composition
DE19747895A1 (de) * 1997-10-30 1999-05-06 Henkel Kgaa Metallbehandlungsflüssigkeit für den neutralen pH-Bereich
FR2809116B1 (fr) * 2000-05-19 2002-08-30 Usinor Utilisation d'une composition huileuse pour le traitement temporaire des surfaces metalliques
DE102011079558A1 (de) * 2011-07-21 2013-01-24 K&P Invest GBR Verwendung von Estern mehrwertiger Carbonsäuren als Betriebsstoff
DE102015210481A1 (de) * 2015-06-09 2016-12-15 Henkel Ag & Co. Kgaa Verwendung von Zitronensäureestern als Korrosionsinhibitor in alkoholischen, als Aerosol versprühbaren kosmetischen Zusammensetzungen

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US3923471A (en) * 1972-03-10 1975-12-02 Nat Steel Corp Lubricated metallic container stocks and method of preparing the same and applying an organic coating thereto
PL131859B1 (en) * 1979-05-09 1985-01-31 Conner Alvin J Metal corrosion inhibitor
US4287741A (en) * 1979-10-09 1981-09-08 National Steel Corporation Lubricated tinplate for drawing and ironing operation

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US7696136B2 (en) 2004-03-11 2010-04-13 Crompton Corporation Lubricant compositions containing hydroxy carboxylic acid and hydroxy polycarboxylic acid esters

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DE3663691D1 (en) 1989-07-06
EP0200001A1 (fr) 1986-11-05
ATE43650T1 (de) 1989-06-15
JPS61230772A (ja) 1986-10-15
DE3610641A1 (de) 1986-10-09

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