EP0031924B1 - Utilisation de sels d'alcanolamines d'acides amidiques cycliques comme inhibiteurs de corrosion dans des systèmes aqueux - Google Patents

Utilisation de sels d'alcanolamines d'acides amidiques cycliques comme inhibiteurs de corrosion dans des systèmes aqueux Download PDF

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Publication number
EP0031924B1
EP0031924B1 EP80107851A EP80107851A EP0031924B1 EP 0031924 B1 EP0031924 B1 EP 0031924B1 EP 80107851 A EP80107851 A EP 80107851A EP 80107851 A EP80107851 A EP 80107851A EP 0031924 B1 EP0031924 B1 EP 0031924B1
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weight
gew
carbon atoms
teile
acid
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EP80107851A
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German (de)
English (en)
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EP0031924A1 (fr
Inventor
Walter Dr.-Chem Trautmann
Elmar Getto
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BASF SE
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BASF SE
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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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—Amides; Imides
    • 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
    • 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
    • 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
    • C10M2215/12—Partial amides of polycarboxylic acids
    • 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
    • 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 the use of alkanolamine salts of cyclic amic acids as corrosion inhibitors in aqueous systems.
  • Certain forms of application e.g. if contact corrosion between different metals is to be prevented, e.g. When machining metal, require higher concentrations of inhibitors so that adequate corrosion protection can be achieved.
  • the low foam of the process medium is of particular importance.
  • the maleic acid salts to be used according to the above-mentioned literature are not sufficient with regard to low foam.
  • the aim of the invention were those substances which do not foam even in higher concentrations - with an otherwise equally good corrosion protection effect.
  • cyclic amide acids of the definition given in claim 1 are at the same time low-foaming and offer very good corrosion protection when they are present as alkanolamine salts.
  • the measure of using such amide acids as alkanolamine salts and thus in water-soluble form may seem obvious, but it has been found that depending on the chain length and structure of the longer alkyl radical bonded to the amide nitrogen, either (if the chain is too long) too strong foaming agents are almost water-insoluble, or if the chain is too short or an n-alkyl chain has no branches, the corrosion protection effect at least decreases significantly.
  • the narrow range of chain length and degree of isomerization according to the invention thus makes it possible to achieve the desired goal; at the same time, the sensitivity to electrolytes also decreases.
  • amic acid salts to be used according to the invention are derived from the cyclic amic acids and alkanolamines as defined.
  • amic acids in which the carboxylic acid and carbonamide groups are adjacent and in which the C atoms bearing these groups are not olefinic can be obtained, for example, by reacting the corresponding cyclic acid anhydrides of the formula (II) in which the circle according to formula (1) is defined in claim 1, with amines of formula (III) in which R 'and R 2 are also defined according to formula (I) in claim 1.
  • the ring can be mononuclear aromatic, for example a benzene ring which can optionally be substituted by C 1 -C 4 -alkyl groups, fluorine, chlorine, bromine atoms, nitro groups or carboxyl groups.
  • cyclopentane, cyclopentene, cyclohexane, cyclohexene, the bicyclo- [2.2.1] -heptane, -heptene residue or the bicyclo- [2.2.2] -octane or -octene residue come in as ring system here Consider.
  • the above-mentioned substituents are also possible here.
  • the preferred anhydrides are e.g. Phthalic, tetrahydrophthalic, hexahydrophthalic or bicyclo- [2.2.1] -hept-2-en-5,6-dicarboxylic acid anhydride as starting compounds.
  • Amines which are reacted with such anhydrides are e.g. primary amines such as isooctylamines, isononylamines, isodecylamines, isoundecylamines and isododecylamines, preferably the isooctylamines and isononylamines or secondary amines such as N-methyl-N-isooctylamines, N-ethyl-N-isooctylamines, N-propyl-N-isooctylamines, N- (n-butyl) -N-isooctylamine, N- (iso-butyl) -N-isooctylamine, N-methyl-N-isononylamine, N-ethyl-N-isononylamine, N- (n-butyl) -N-isononylamine, N- (iso-buty
  • N-Methyl-N-isooctyl- and -isononylamines are particularly preferred here.
  • amines can be used in a mixture with corresponding nC 8 -C 12 -alkyl- or C 1 - to C 4 -alkyl-nC 8 -C 12 -alkylamines, in an amount such that the later end products up to 90% by weight. -% - related on alkanolamine salt - contained on the corresponding n-alkylamide acid salts.
  • These mixtures originate, for example, from oxo synthesis.
  • the anhydrides can be reacted with the amines by customary methods, which require no special explanation.
  • amic acids obtained are then neutralized in a manner known per se with the alkanolamines.
  • Alkanolamines may be all the relevant agents when they are capable of forming water-soluble salts, ie mainly C 2 - to C 4 alkanolamines or NC i - C 4 alkyl-C 2 - to C 4 -alkanolamines.
  • alkanolamines derived from ethylenediamine can also be considered, for example 4-fold ethoxylated or propoxylated ethylenediamine.
  • N-2-ethylhexyl-, N-methyl-N- (2-ethylhexyl) -, the N-isonyl- and the N-methyl-N-isononylhalamides of phthalic acid and tetrahydrophthalic acid which have been found to be particularly effective inhibitors, have also been found to be effective Triethanolamine or Diethanolamine have been neutralized.
  • anti-corrosion agents have been found that are extremely effective in aqueous systems and practically do not foam even in higher application concentrations.
  • the agents are added to the process media in an amount of 0.01 to 5% by weight, based on the medium. Exceeding and falling short are possible, but do not bring any additional advantages.
  • the corrosion protection effect is demonstrated in 1% and 2% aqueous solution of active substance and in various water hardnesses using the Herbert test system introduced in the metalworking sector.
  • This consists of a standardized gray cast iron plate and also standardized steel chips of 5 mm length, which are supplied by Alfred Herbert, Coventry / England.
  • the square plate with the dimensions 100 X 100 X 5 mm is carefully sanded before testing using a belt grinder with 120 corundum emery belt, washed with white spirit and ethanol and dried with a clean cloth.
  • the steel chips supplied with the test system which are obtained under standardized conditions from 0.40% carbon steel, are placed on the prepared cast steel plate in four piles using a suitable metal or plastic spoon with the capacity of a normal teaspoon so that they separate from each other and have the same distance from the edges of the plate.
  • the chips should lie in a single layer in the narrowest possible position.
  • the solutions or emulsions to be tested for their corrosion behavior are applied to the piles of chips by means of a measuring pipette in such a quantity that the liquid reaching the cast steel plate is held together by the chips. After standing for 24 hours in an atmosphere of 70% relative humidity, the chips are shaken off the plate by tilting. The clearly visible outline of the dried aqueous medium remains. Depending on the corrosiveness of the liquid, rust marks of smaller or larger extent have formed at the contact points of the chips, which could also have grown together to form a closed rust layer. The assessment can be made by visually estimating the percentage of rust in the area.
  • the impact method was used based on DIN 53 902.
  • the simple test procedure was sufficient, in which the punch with the perforated plate was manually inserted and removed 30 times in 30 s and then carefully pulled out (IG impact method).
  • the foam volume is on the graded Foam cylinder after 1, 5 and 10 min. read in ml. Information about temperature, concentration and water hardness are also important.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Lubricants (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)

Claims (2)

1. Utilisation en tant qu'inhibiteurs de corrosion dans des systèmes aqueux, de sels alcanolaminés d'amides-acides de formule (I)
Figure imgb0007
dans laquelle le cercle représente un noyau aromatique monocyclique ou un système de noyaux aliphatiques mono- ou bicycliques avec, chaque fois, 5 ou 6 atomes de C par noyau, R' représente un radical isoalcoyle dont la chaîne la plus longue contient 6 à 8 atomes de C et qui a un nombre total de carbone de 8 à 12 atomes de C, et R2 représente un radical alcoyle à 1-4 atomes de C ou un hydrogène, les groupes carboxyle ou carbonamide étant fixés sur des atomes de C non oléfiniques et étant situés en positions voisines.
2. Utilisation de sels selon la revendication 1, caractérisée en ce qu'on utilise en plus jusqu'à 90% en poids
- par rapport à la totalité de tous les sels alcanolaminés
- de sels alcanolaminés de composés de formule (I) dans lesquels R' représente un radical n-alcoyle à 8-12 atomes de C et R2 un radical alcoyle à 1-4 atomes de C ou un hydrogène.
EP80107851A 1979-12-21 1980-12-12 Utilisation de sels d'alcanolamines d'acides amidiques cycliques comme inhibiteurs de corrosion dans des systèmes aqueux Expired EP0031924B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2951542 1979-12-21
DE19792951542 DE2951542A1 (de) 1979-12-21 1979-12-21 Verwendung von alkanolaminsalzen cyclischer amidsaeuren als korrosionsschutzmittel in waessrigen systemen

Publications (2)

Publication Number Publication Date
EP0031924A1 EP0031924A1 (fr) 1981-07-15
EP0031924B1 true EP0031924B1 (fr) 1983-05-18

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EP80107851A Expired EP0031924B1 (fr) 1979-12-21 1980-12-12 Utilisation de sels d'alcanolamines d'acides amidiques cycliques comme inhibiteurs de corrosion dans des systèmes aqueux

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DE (2) DE2951542A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4379063A (en) * 1981-02-20 1983-04-05 Cincinnati Milacron Inc. Novel functional fluid
DE3719101A1 (de) * 1987-06-06 1988-12-15 Bayer Ag Neue korrosionsinhibitoren
EP0486510B1 (fr) * 1989-08-08 1996-02-14 Stepan Company Tensio-actifs amidocarboxy cycliques, leur synthese et leur emploi
WO1999022082A2 (fr) 1997-10-24 1999-05-06 D.D.C. Planungs-, Entwicklungs- Und Management Ag Dispositif et procede pour la realisation d'une construction et construction ainsi realisee

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2944969A (en) * 1957-02-06 1960-07-12 Petrolite Corp Prevention of rust and corrosion
US3231607A (en) * 1962-03-29 1966-01-25 Chevron Res Partial amides of benzene polycarboxylic acids
US3704090A (en) * 1971-04-26 1972-11-28 Hexcel Corp Corrosion inhibition using n-aminoalkyl phthalamides
FR2268791A1 (en) * 1974-04-25 1975-11-21 Nobel Hoechst Chimie Para-alkyl benzoic acid alkanolamine condensate - useful as water-soluble or dispersable corrosion inhibitors for ferrous metals
FR2427400A1 (fr) * 1978-06-02 1979-12-28 Snam Progetti Agent anti-rouille pour systemes aqueux et compositions lubrifiantes empechant la rouille

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2944969A (en) * 1957-02-06 1960-07-12 Petrolite Corp Prevention of rust and corrosion
US3231607A (en) * 1962-03-29 1966-01-25 Chevron Res Partial amides of benzene polycarboxylic acids
US3704090A (en) * 1971-04-26 1972-11-28 Hexcel Corp Corrosion inhibition using n-aminoalkyl phthalamides
FR2268791A1 (en) * 1974-04-25 1975-11-21 Nobel Hoechst Chimie Para-alkyl benzoic acid alkanolamine condensate - useful as water-soluble or dispersable corrosion inhibitors for ferrous metals
FR2427400A1 (fr) * 1978-06-02 1979-12-28 Snam Progetti Agent anti-rouille pour systemes aqueux et compositions lubrifiantes empechant la rouille

Also Published As

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DE3063379D1 (en) 1983-07-07
EP0031924A1 (fr) 1981-07-15
DE2951542A1 (de) 1981-07-02

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