EP0109549B1 - Agents anti-corrosion pour solutions aqueuses pour le traitement des métaux et procédé pour leur préparation - Google Patents

Agents anti-corrosion pour solutions aqueuses pour le traitement des métaux et procédé pour leur préparation Download PDF

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Publication number
EP0109549B1
EP0109549B1 EP83110410A EP83110410A EP0109549B1 EP 0109549 B1 EP0109549 B1 EP 0109549B1 EP 83110410 A EP83110410 A EP 83110410A EP 83110410 A EP83110410 A EP 83110410A EP 0109549 B1 EP0109549 B1 EP 0109549B1
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Prior art keywords
formula
denotes
compound
mono
group
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.)
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EP83110410A
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German (de)
English (en)
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EP0109549A1 (fr
Inventor
Francesco Dr. Cargnino
Giuseppe Dr. Natoli
Horst Lorke
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.)
Hoechst AG
Hoechst Italia SpA
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Hoechst AG
Hoechst Italia SpA
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Publication of EP0109549A1 publication Critical patent/EP0109549A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C23—COATING 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
    • C23F—NON-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
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting 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
    • C23F11/14—Nitrogen-containing compounds
    • C23F11/145—Amides; N-substituted amides
    • 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
    • C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
    • 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
    • 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
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
    • C10M2215/082—Amides [having hydrocarbon substituents containing less than thirty carbon atoms] containing hydroxyl groups; Alkoxylated 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/086—Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/12—Partial amides of polycarboxylic acids
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/12—Partial amides of polycarboxylic acids
    • C10M2215/122—Phtalamic acid
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/26—Amines
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • 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
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • 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

Definitions

  • the invention relates to anti-corrosion agents, particularly suitable for use as anti-corrosion agents for processing metals.
  • the present invention also relates to a method for producing these anti-corrosion agents.
  • the present invention relates to aqueous liquids containing no oils for working metals, especially metals exposed to corrosion
  • cooling lubricants containing no oils are often used.
  • These cooling lubricants which contain no oils, are essentially combinations of salts of organic acids, for example para-tertiary-butylbenzoic acid, or of isononanoic acid with water-soluble polyadducts, those of ethylene oxide and of propylene oxide and / or butylene oxide with compounds are obtained which have active hydrogen atoms.
  • the known disadvantage is that there is a tendency to a degreasing effect, in particular due to thermal influences, due to the change in the pH range or due to a change in the electrolyte charge. Consequently, a change in the composition and in the activity of the emulsion is caused, whereby after a certain time the emulsion in circulation is no longer able to perform neither the required corrosion protection nor the necessary lubrication activity.
  • Another disadvantage of mineral oil emulsions is that they Milky appearance makes it difficult to observe the machining process.
  • the inadequate corrosion protection effect is also present in the case in which the above-mentioned salts of organic acids are precipitated out due to the action of the ions which contribute to the hardness of the water, with a disadvantageous shift in the mixture consisting of corrosion and lubricants that are present in the coolant solutions. As a result, significant corrosion of both the tool and the workpiece can be caused during the operation.
  • These compounds of formula (I) are obtained by using one mole of a polyamine of the formula reacted with one mole of an alkylamine or hydroxyalkylamine and with 2 moles of an anhydride of the formula optionally the reaction product is methylolated with formaldehyde and the compound of the formula (I) obtained in the form of the free acid is neutralized with a mono-, di- or triethanolamine or with isopropanolamine.
  • the procedure is such that polyamine and the monoamine are added to the reaction vessel in the proportions given above and heated to a temperature of about 20-150 ° C., preferably 80-100 ° C.
  • the presence of an inert organic solvent is possible, but not essential.
  • the reaction can also be carried out in the melt without a solvent.
  • the amount of anhydride indicated above is slowly added at the indicated reaction temperature over a period of about 2 hours, the reaction temperature rising to about 120-140 ° C.
  • the corresponding free acids can be used successfully in many cases.
  • the water of reaction formed can remain in the reaction vessel; the amide of the formula (I) in which R 1 is di-alkylamino or di-hydroxy-alkylamino is then obtained.
  • the product thus obtained is a liquid that is soluble in water.
  • This product is diluted with monoethanolamine, diethanolamine or triethanolamine to a content of 50% and a very effective cooling lubricant is thus obtained.
  • the product obtained is a yellow liquid which is soluble in water. Diluted with an alkanolamine, this gives a good cooling lubricant.
  • a water-soluble product is obtained, which is diluted with an alkanolamine and is a very effective cooling lubricant.
  • phthalic anhydride 110 g are added to 30 g of ethylenediamine and 31 g of monoethanolamine and the mixture is heated to 120 ° C. To dissolve completely, the temperature is raised to 130-140 ° C. and then 30 g of monoethanolamine and 60 g of water are added. A yellow liquid which is readily miscible with water is obtained.
  • the new compounds of formula 1 are preferably used as corrosion inhibitors in aqueous liquids containing no oils and in the production of aqueous liquids containing no oils for the processing of metals.
  • the aqueous liquids mentioned, which do not contain oils, are used primarily for metalworking processes without cutting and with cutting, in particular for processing iron or ferrous metals. Because of the use of the compounds according to the invention, all those disadvantages with which the mineral oil emulsions and also the abovementioned cooling lubricants containing no oils are afflicted are avoided.
  • a major advantage of the cooling lubricants which contain no oils and which are produced using the new compounds of the formula I according to the invention consists in the fact that these new products have a greater corrosion protection effect than the lubricants of the known technology.
  • the aqueous cooling agents which contain no oils and which are prepared by adding the new products of the formula I according to the invention can be used in a very wide range of applications.
  • the lubricants according to the invention maintain high stability and high activity during their use.
  • the compounds of the formula of the invention exert such a high corrosion protection effect that an addition in weight between about 0.5% and 5.0% is sufficient to give cooling lubricants which do not contain oils the required corrosion protection effect even in cases where Metal surfaces are particularly exposed to corrosion.
  • the preferred proportion by weight when using the compounds of the formula (I) according to the invention in aqueous cooling lubricants containing no oils is between 1% and 2%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)

Claims (5)

1. Composés de formule
Figure imgb0019
dans laquelle
R représente l'hydrogène ou un groupe hydroxyméthyle,
R1 un groupe mono-(Cy-C5)-alkylamino, di-(C2-C5) alkylamino, mono-(C2-C5)-hydroxyalkylamino ou di-(C2-C5)-hydroxyalkylamino,
ou bien R1 et R représentent ensemble une liaison directe, l'atome d'azote étant alors directement lié à l'atome de carbone,
R2 représente l'hydrogène ou un groupe hydroxyméthyle,
R3 un groupe
Figure imgb0020
n est le nombre 2 ou 3,
m un nombre compris entre 1 et 4 et
M un groupe mono-, di- ou tri-éthanolammonium ou iso-propanolammonium.
2. Composés selon la revendication 1 dans lesquels
R1 est un groupe di-(C2-C5)-hydroxyalkylamino, en particulier di-hydroxyéthylamino, et
R3 un groupe
Figure imgb0021
3. Procédé de préparation des composés selon la revendication 1, caractérisé en ce que l'on fait réagir un mole d'une polyamine de formule
Figure imgb0022
avec une mole d'une alkylamine ou d'un hydroxyalkylamines et 2 moles d'un anhydride de formule
Figure imgb0023
éventuellement on méthylole le produit de la réaction avec du formaldéhyde, et on neutralise le composé de formule 1 obtenu sous la forme de l'acide libre avec la mono-, di- ou tri-éthanolamine ou avec l'isopropanolamine.
4. Utilisation des composés selon la revendication 1 comme agents de protection contre la corrosion dans des liquides aqueux.
5. Utilisation des composés selon la revendication 1 comme agents de protection contre la corrosion dans des produits lubrifiants et de refroidissement dans des liquides aqueux.
EP83110410A 1982-10-25 1983-10-19 Agents anti-corrosion pour solutions aqueuses pour le traitement des métaux et procédé pour leur préparation Expired EP0109549B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT2390282 1982-10-25
IT23902/82A IT1191045B (it) 1982-10-25 1982-10-25 Additivi anti-corrosione per liquidi acquosi per la lavorazione di metalli e procedimento per la loro preparazione

Publications (2)

Publication Number Publication Date
EP0109549A1 EP0109549A1 (fr) 1984-05-30
EP0109549B1 true EP0109549B1 (fr) 1988-08-31

Family

ID=11210758

Family Applications (1)

Application Number Title Priority Date Filing Date
EP83110410A Expired EP0109549B1 (fr) 1982-10-25 1983-10-19 Agents anti-corrosion pour solutions aqueuses pour le traitement des métaux et procédé pour leur préparation

Country Status (6)

Country Link
US (1) US4552678A (fr)
EP (1) EP0109549B1 (fr)
JP (1) JPS59130251A (fr)
BR (1) BR8305873A (fr)
DE (1) DE3377869D1 (fr)
IT (1) IT1191045B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3341013A1 (de) * 1983-11-12 1985-05-23 Henkel KGaA, 4000 Düsseldorf Bernsteinsaeure-mono-dialkylamide als wasserloesliche korrosionsschutzmittel
US4749503A (en) * 1986-03-07 1988-06-07 Chemical Exchange Industries, Inc. Method and composition to control microbial growth in metalworking fluids
US5470908A (en) * 1993-10-28 1995-11-28 The Dow Chemical Company Water-based acrylic coating compositions
DE102014203659A1 (de) * 2014-02-28 2015-09-03 Siemens Aktiengesellschaft Kühlvorrichtung für einen Konverter einer Hochspannungs-Gleichstrom-Übertragungsanlage

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4168292A (en) * 1977-10-26 1979-09-18 Petrolite Corporation Acylated hydroxyalkylaminoalkylamides and preparation thereof and uses thereof as corrosion inhibitors
IT1098305B (it) * 1978-06-02 1985-09-07 Snam Progetti Antiruggine per sistemi acquosi e composizione lubrificante antiruggine
DE3222996A1 (de) * 1981-06-22 1983-03-03 Basf Ag, 6700 Ludwigshafen Alkanolaminsalze cyclischer amidsaeuren und ihre verwendung als korrosionsschutzmittel in waessrigen systemen
US4374741A (en) * 1981-07-21 1983-02-22 Cincinnati Milacron Inc. Polyamide and functional fluid containing same

Also Published As

Publication number Publication date
IT1191045B (it) 1988-02-24
IT8223902A1 (it) 1984-04-25
IT8223902A0 (it) 1982-10-25
JPS59130251A (ja) 1984-07-26
US4552678A (en) 1985-11-12
BR8305873A (pt) 1984-05-29
EP0109549A1 (fr) 1984-05-30
DE3377869D1 (en) 1988-10-06

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