EP0109548B1 - Corrosion inhibitors for aqueous solutions for the treatment of metals, and process for their preparation - Google Patents
Corrosion inhibitors for aqueous solutions for the treatment of metals, and process for their preparation Download PDFInfo
- Publication number
- EP0109548B1 EP0109548B1 EP83110409A EP83110409A EP0109548B1 EP 0109548 B1 EP0109548 B1 EP 0109548B1 EP 83110409 A EP83110409 A EP 83110409A EP 83110409 A EP83110409 A EP 83110409A EP 0109548 B1 EP0109548 B1 EP 0109548B1
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- EP
- European Patent Office
- Prior art keywords
- formula
- denotes
- compound
- metals
- corrosion
- 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.)
- Expired
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- FEYLYTBPPCYZLO-UHFFFAOYSA-N CC1C(C)CC=CC1 Chemical compound CC1C(C)CC=CC1 FEYLYTBPPCYZLO-UHFFFAOYSA-N 0.000 description 1
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
- 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
Definitions
- the present invention relates to anticorrosive agents, particularly suitable for use as an anticorrosive agent for aqueous liquids 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 processing metals, especially metals particularly exposed to corrosion.
- machining processes for processing metals such as drilling, turning, milling, broaching, and the like. a. m. and even in the case of deformations of metals without chip removal, aqueous mineral oil emulsions are used, or in recent times to a greater extent no cooling lubricants containing oils have been used.
- cooling lubricants containing no oils are essentially combinations of salts or 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.
- Another disadvantage of the mineral oil emulsion is that its milky appearance makes it difficult to observe the machining process.
- the anti-corrosion agents used for these aqueous coolants containing no oils i.e. the above-mentioned salts of organic acids always have the considerable disadvantage that they offer insufficient resistance to hard water and inadequate protection against corrosion.
- the inadequate corrosion protection effect is also present in the case in which the abovementioned salts of the 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 is present in the cooling lubricant solutions. As a result, significant corrosion of both the tool and the workpiece can be caused during the operation.
- New compounds have now been found, particularly suitable as an anti-corrosion agent for aqueous liquids, for example for cleaning metals and in particular as an anti-corrosion agent for the production of non-oil-containing aqueous liquids which are suitable for working with metals.
- M means mono-, di- or triethanolammonium or iso-propanolammonium.
- R I is a group of the formulas: and R 2 represents styryl.
- These compounds of formula (I) are obtained by mixing 1 mole of a polyamine of the formula reacted with one mole of an acid of the formula and one mole 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 to heat the polyamine and the acid in a molar ratio of 1: 1 to a temperature of approximately 120 to 160 ° C. The reaction mixture is kept at this temperature until the reaction is complete and the corresponding water of reaction is distilled off.
- a mixture of 103 g (1 mol) of diethylenetriamine and 148 g (1 mol) of cinnamic acid is heated to a temperature of 1450 ° C. and 17 ml of water are distilled off in the course. The temperature is then allowed to drop to 120 ° C. and 145 g of phthalic anhydride (1 mol) are added in small amounts over two hours in such a way that the temperature is kept at 120 ° C.
- Example 1 179 g (1 mol) of tert-butylbenzoic acid and 103 g (1 mol) of diethylenetriamine are reacted as indicated in Example 1. 148 g (1 mol) of phthalic anhydride are then slowly added at 120 ° C. until everything has dissolved. Then 61 g (1 mol) of monoethanolamine and 180 g of water are added and the mixture is allowed to cool. A product with the same properties as in Example 1 is obtained.
- Example 1 158 g (1 mol) of isononanoic acid and 103 g (1 mol) of diethylenetriamine are reacted as indicated in Example 1. 148 g (1 mol) of phthalic anhydride are then slowly added at 120 ° C. until everything has dissolved. Then 105 g (1 mol) of diethanolamine and 180 g of water are added and the mixture is allowed to cool. A product with the same properties as in Example 1 is obtained.
- the new compounds of the formula (I) 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 above-mentioned aqueous liquids containing no oils are used primarily for metal-working processes without cutting and with cutting, in particular for the processing of iron or ferrous metals. Due to 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 containing no oils, which are produced using the new compounds of the formula (I) according to the invention, is that these new products have a greater corrosion protection effect than the lubricants of the known technology.
- the aqueous cooling lubricants containing no oils, which are produced 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 (I) according to the invention exert such a high corrosion protection effect that an addition in weight between approximately 0.5% and 5.0% is sufficient to impart the required corrosion protection effect to cooling lubricants which do not contain oils, 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%.
Description
Die vorliegende Erfindung betrifft Korrosionsschutzmittel, insbesondere geeignet für die Verwendung als Korrosionsschutzmittel für wässrige Flüssigkeiten zur Bearbeitung von Metallen.The present invention relates to anticorrosive agents, particularly suitable for use as an anticorrosive agent for aqueous liquids for processing metals.
Die vorliegende Erfindung betrifft überdies ein Verfahren zur Herstellung dieser Korrosionsschutzmittel. Die vorliegende Erfindung betrifft schliesslich wässrige, keine Öle enthaltende Flüssigkeiten zur Bearbeitung von Metallen, vor allem von der Korrosion besonders ausgesetzten Metallen. Bei spanabhebenden Verfahren zur Bearbeitung von Metallen, wie beispielsweise Bohren, Drehen, Fräsen, Räumen, u. a. m. und auch bei Verformungen von Metallen ohne Spanabhebung, werden oft wässrige Mineralölemulsionen oder in letzter Zeit in grösserem Ausmass keine Öle enthaltende Kühlschmiermittel verwendet. Bei diesen, keine Öle enthaltenden Kühlschmiermitteln handelt es sich im wesentlichen um Kombinationen von Salzen oder organischen Säuren, zum Beispiel der para-tertiär-Butylbenzoesäure, oder von Isononan-Säure mit wasserlöslichen Polyadduktstoffen, die von Ethylenoxid und von Propylenoxid und/oder Butylenoxid mit Verbindungen erhalten werden, die aktive Wasserstoffatome besitzen.The present invention also relates to a method for producing these anti-corrosion agents. Finally, the present invention relates to aqueous liquids containing no oils for processing metals, especially metals particularly exposed to corrosion. In machining processes for processing metals, such as drilling, turning, milling, broaching, and the like. a. m. and even in the case of deformations of metals without chip removal, aqueous mineral oil emulsions are used, or in recent times to a greater extent no cooling lubricants containing oils have been used. These cooling lubricants containing no oils are essentially combinations of salts or 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.
Bei Verwendung der wässrigen Mineralöllösungen als Kühlflüssigkeiten bei der Metallverarbeitung liegt der bekannte Nachteil darin, dass die Neigung zu einem Entfettungseffekt besteht, und zwar insbesondere aufgrund, von thermischen Einflüssen, aufgrund der Änderung des pH-Bereiches oder aufgrund eines Wechsels der Elektrolytladung. Folglich wird eine Veränderung in der Zusammensetzung und in der Aktivität der Emulsion hervorgerufen, wodurch nach einer gewissen Zeit die sich im Umlauf befindliche Emulsion nicht mehr fähig ist, weder die erforderliche Korrosionsschutztätigkeit noch die notwendige Schmiertätigkeit auszuüben. Ein weiterer Nachteil der Mineralölemulsion besteht darin, dass ihr milchiges Aussehen die Beobachtung des Bearbeitungsablaufes erschwert. Einige dieser, den Mineralölemulsionen anhaftenden Nachteile weisen nicht die zur Zeit verwendeten, keine Öle enthaltenden, wässrigen Kühlschmiermittel auf.When using the aqueous mineral oil solutions as cooling liquids in metal processing, 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. Another disadvantage of the mineral oil emulsion is that its milky appearance makes it difficult to observe the machining process. Some of these disadvantages inherent in mineral oil emulsions do not have the currently used, oil-free, aqueous cooling lubricants.
Die für diese wässrigen, keine Öle enthaltenden Kühlschmiermittel verwendeten Korrosionsschutzmittel, d.h. die oben genannten Salze der organischen Säuren, weisen dennoch immer den erheblichen Nachteil auf, dass sie einen ungenügenden Widerstand zum harten Wasser und einen mangelhaften Schutz gegen die Korrosion bieten.The anti-corrosion agents used for these aqueous coolants containing no oils, i.e. the above-mentioned salts of organic acids always have the considerable disadvantage that they offer insufficient resistance to hard water and inadequate protection against corrosion.
Die ungenügende Korrosionsschutzwirkung liegt auch im Falle vor, bei dem die oben genannten Salze der organischen Säuren durch Fällung ausgeschieden werden, und zwar zufolge der Einwirkung der zur Härte des Wassers beitragenden Jonen, wobei eine nachteilhafte Verschiebung der aus Korrosions- und Schmiermitteln bestehenden Mischung erfolgt, die in den Kühlschmiermittellösungen vorhanden ist. Folglich kann während des Arbeitsvorgangs eine erhebliche Korrosion sowohl des Werkzeugs als auch des Werkstücks verursacht werden.The inadequate corrosion protection effect is also present in the case in which the abovementioned salts of the 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 is present in the cooling lubricant solutions. As a result, significant corrosion of both the tool and the workpiece can be caused during the operation.
Nun wurden neue Verbindungen gefunden, insbesondere geeignet als Korrosionsschutzmittel für wässrige Flüssigkeiten, zum Beispiel zur Reinigung von Metallen und insbesondere als Korrosionsschutzmittel zur Herstellung von keine Öle enthaltenden, wässrigen Flüssigkeiten, die sich für die Bearbeitung von Metallen eignen.New compounds have now been found, particularly suitable as an anti-corrosion agent for aqueous liquids, for example for cleaning metals and in particular as an anti-corrosion agent for the production of non-oil-containing aqueous liquids which are suitable for working with metals.
Die erfindungsgemässen Korrosionsschutzmittel entsprechen der folgenden Formel (I)
- R Wasserstoff oder Hydroxymethyl,
- R' eine Gruppe, entsprechend einer der folgenden Formeln
- R2 Wasserstoff, C,-C'2-Alkyl, Cl-Cs-Hydroxyalkyl, Phenyl, tert.-Butylphenyl oder Styryl,
- n 2 oder 3,
- m eine Zahl zwischen 1 und 4 und
- R is hydrogen or hydroxymethyl,
- R 'is a group according to one of the following formulas
- R 2 is hydrogen, C, -C '2 -alkyl, C 1 -C s -hydroxyalkyl, phenyl, tert-butylphenyl or styryl,
- n 2 or 3,
- m is a number between 1 and 4 and
M Mono-, Di- oder Triethanolammonium oder iso-Propanolammonium bedeutet.M means mono-, di- or triethanolammonium or iso-propanolammonium.
Bevorzugt sind die Verbindungen der obigen Formel (I), worin RI eine Gruppe der Formeln:
Man erhält diese Verbindungen der Formel (I), indem man 1 Mol eines Polyamins der Formel
Will man eine Verbindung der Formel (I) erhalten mit der Bedeutung von R = Hydroxymethyl, so kann man das Reaktionsprodukt vor der Neutralisation nach bekannten Methoden mit Formaldehyd oder Formaldehyd abgebenden Verbindungen umsetzen. Man kann diese Methylolierung vollständig oder nur teilweise durchführen, im letztgenannten Fall erhält man dann ein Gemisch der Verbindungen mit R = H und R = Hydroxymethyl.If one wishes to obtain a compound of formula (I) with the meaning of R = hydroxymethyl, the reaction product can be reacted with formaldehyde or formaldehyde-releasing compounds before neutralization by known methods. This methylolation can be carried out completely or only partially, in the latter case a mixture of the compounds with R = H and R = hydroxymethyl is then obtained.
Nach beendeter Reaktion gibt man vor dem Abkühlen noch Wasser zu, mindestens 3 Mol, bezogen auf ein Mol Polyamin und lässt abkühlen. Man erhält die Verbindung der Formel (I) in Form der freien Säure, die dann für den Gebrauch durch Zugabe von Mono-, Di- oder Triethanolamin oder iso-Propanolamin auf einen pH-Wert von 8 bis 10, vorzugsweise 9 eingestellt wird.After the reaction has ended, water is added before cooling, at least 3 moles, based on one mole of polyamine, and the mixture is allowed to cool. The compound of formula (I) is obtained in the form of the free acid, which is then adjusted to a pH of 8 to 10, preferably 9, for use by adding mono-, di- or triethanolamine or iso-propanolamine.
Man erhitzt ein Gemisch aus 103 g (1 Mol) Diethylentriamin und 148 g (1 Mol) Zimtsäure auf eine Temperatur von 1450C und destilliert im Verlauf 17 ml Wasser ab. Dann lässt man die Temperatur auf 120°C absinken und gibt während zwei Stunden 145 g Phthalsäureanhydrid (1 Mol) in kleinen Mengen so zu, dass die Temperatur von 120°C gehalten wird.A mixture of 103 g (1 mol) of diethylenetriamine and 148 g (1 mol) of cinnamic acid is heated to a temperature of 1450 ° C. and 17 ml of water are distilled off in the course. The temperature is then allowed to drop to 120 ° C. and 145 g of phthalic anhydride (1 mol) are added in small amounts over two hours in such a way that the temperature is kept at 120 ° C.
Dann gibt man 60 g (1 Mol) Monoethanolamin und 150 g Wasser zu. Das so erhaltene Produkt stellt eine rote Flüssigkeit dar, die mit Wasser mischbar ist und sehr gute Kühlschmiermitteleigenschaften zeigt.Then 60 g (1 mol) of monoethanolamine and 150 g of water are added. The product thus obtained is a red liquid which is miscible with water and has very good cooling lubricant properties.
179 g (1 Mol) tert.-Butylbenzoesäure und 103 g (1 Mol) Diethylentriamin werden, wie in Beispiel 1 angegeben, umgesetzt. Bei 120°C gibt man dann langsam 148 g (1 Mol) Phthalsäureanhydrid zu bis sich alles gelöst hat. Dann gibt man noch 61 g (1 Mol) Monoethanolamin und 180 g Wasser zu und lässt abkühlen. Man erhält ein Produkt mit den gleichen Eigenschaften wie in Beispiel 1.179 g (1 mol) of tert-butylbenzoic acid and 103 g (1 mol) of diethylenetriamine are reacted as indicated in Example 1. 148 g (1 mol) of phthalic anhydride are then slowly added at 120 ° C. until everything has dissolved. Then 61 g (1 mol) of monoethanolamine and 180 g of water are added and the mixture is allowed to cool. A product with the same properties as in Example 1 is obtained.
158 g (1 Mol) Isononansäure und 103 g (1 Mol) Diethylentriamin werden, wie in Beispiel 1 angegeben, umgesetzt. Bei 120°C gibt man dann langsam 148 g (1 Mol) Phthalsäureanhydrid zu bis sich alles gelöst hat. Dann gibt man noch 105 g (1 Mol) Diethanolamin und 180 g Wasser zu und lässt abkühlen. Man erhält ein Produkt mit den gleichen Eigenschaften wie in Beispiel 1.158 g (1 mol) of isononanoic acid and 103 g (1 mol) of diethylenetriamine are reacted as indicated in Example 1. 148 g (1 mol) of phthalic anhydride are then slowly added at 120 ° C. until everything has dissolved. Then 105 g (1 mol) of diethanolamine and 180 g of water are added and the mixture is allowed to cool. A product with the same properties as in Example 1 is obtained.
Die neuen Verbindungen der Formel (I) werden vorzugsweise als Korrosionsschutzmittel in wässrigen, keine Öle enthaltenden Flüssigkeiten und in der Herstellung von wässrigen, keine Öle enthaltenden Flüssigkeiten für die Bearbeitung von Metallen verwendet. Die genannten, wässrigen, keine Öle enthaltenden Flüssigkeiten werden vor allem für Metallbearbeitungsverfahren ohne Spanabhebung und mit Spanabhebung, insbesondere für die Bearbeitung von Eisen oder eisenhaltigen Metallen verwendet. Aufgrund der Verwendung der erfindungsgemässen Verbindungen werden alle jene Nachteile vermieden, mit denen die Mineralölemulsionen und auch die obengenannten, keine Öle enthaltenden Kühlschmiermittel behaftet sind. Ein wesentlicher Vorteil der keine Öle enthaltenden Kühlschmiermittel, die mit Verwendung der neuen, erfindungsgemässen Verbindungen der Formel (I) hergestellt werden, besteht in einer gegenüber den Schmiermitteln der bekannten Technik grösseren Korrosionsschutzwirkung dieser neuen Produkte. Die wässrigen, keine Öle enthaltenden Kühlschmiermittel, die mit Zugabe der neuen erfindungsgemässen Produkte der Formel (I) hergestellt werden, sind auf einem sehr weiten Anwendungsgebiet verwendbar. Die erfindungsgemässen Schmiermittel bewahren eine hohe Stabilität und eine hohe Aktivität während ihrer Benutzung. Die erfindungsgemässen Verbindungen der Formel (I) üben eine derart hohe Korrosionsschutzwirkung aus, dass eine Zugabe in Gewicht zwischen ca. 0,5% und 5,0% genügt, um Kühlschmiermitteln, die keine Öle enthalten, die geforderte Korrosionsschutzwirkung auch in Fällen zu verleihen, bei denen Metalloberflächen der Korrosion besonders ausgesetzt sind. Der bevorzugte Gewichtsanteil bei der Verwendung der erfindungsgemässen Verbindungen der Formel (I) in wässrigen, keine Öle enthaltenden Kühlschmiermitteln liegt zwischen 1 % und 2%.The new compounds of the formula (I) 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 above-mentioned aqueous liquids containing no oils are used primarily for metal-working processes without cutting and with cutting, in particular for the processing of iron or ferrous metals. Due to 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 containing no oils, which are produced using the new compounds of the formula (I) according to the invention, is that these new products have a greater corrosion protection effect than the lubricants of the known technology. The aqueous cooling lubricants containing no oils, which are produced 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 (I) according to the invention exert such a high corrosion protection effect that an addition in weight between approximately 0.5% and 5.0% is sufficient to impart the required corrosion protection effect to cooling lubricants which do not contain oils, 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%.
Die Vorteile der neuen Produkte gegenüber bekannten wasserlöslichen Korrosionsschutzmitteln wie Alkanolamin-Salzen der Isononansäure oder der para-tert.-Butylbenzoesäure sind aus den in der nachfolgenden Tabelle zusammengestellten Untersuchungsergebnissen ersichtlich. Bei diesen Untersuchungen wurden Löslichkeit, Schaumverhalten und Korrosionsschutzeigenschaften der angeführten Produkte miteinander verglichen. Für die Bestimmung der Löslichkeit wurde das Aussehen einer 3%igen wässrigen Lösung nach 24 stündigem Stehen herangezogen. Die Prüfung des Schaumverhaltens erfolgte nach DIN 53902 und die Korrosion wurde vergleichend geprüft unter Berücksichtigung molarer Verhältnisse:
- A) 22 Gew.-% Isononansäure
- 63 Gew.-% Triethanolamin
- 15 Gew.-% H2O
- B) 25 Gew.-% p-tert-Butylbenzoesäure
- 60 Gew.-% Triethanolamin
- 15 Gew.-% H20
- C) 40 Gew.-% Produkt gemäss Beispiel 1
- 45 Gew.-% Triethanolamin
- 15 Gew.-% H20
- D) 35 Gew.-% Produkt gemäss Beispiel 2
- 50 Gew.-% Triethanolamin
- 15 Gew.-% H20
- E) 35 Gew.-% Produkt gemäss Beispiel 3
- 50 Gew.-% Triethanolamin
- 15 Gew.-% H20
- A) 22% by weight isononanoic acid
- 63% by weight of triethanolamine
- 15% by weight H 2 O
- B) 25% by weight of p-tert-butylbenzoic acid
- 60% by weight triethanolamine
- 15% by weight H 2 0
- C) 40% by weight of product according to Example 1
- 45% by weight of triethanolamine
- 15% by weight H 2 0
- D) 35% by weight of product according to Example 2
- 50% by weight of triethanolamine
- 15% by weight H 2 0
- E) 35% by weight of product according to Example 3
- 50% by weight of triethanolamine
- 15 wt% H20
Claims (5)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT2390382 | 1982-10-25 | ||
IT23903/82A IT1191046B (en) | 1982-10-25 | 1982-10-25 | ANTI-CORROSION ADDITIVES FOR AQUEOUS LIQUIDS FOR METAL PROCESSING AND PROCEDURE FOR THEIR PREPARATION |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0109548A1 EP0109548A1 (en) | 1984-05-30 |
EP0109548B1 true EP0109548B1 (en) | 1988-07-13 |
Family
ID=11210763
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP83110409A Expired EP0109548B1 (en) | 1982-10-25 | 1983-10-19 | Corrosion inhibitors for aqueous solutions for the treatment of metals, and process for their preparation |
Country Status (6)
Country | Link |
---|---|
US (1) | US4533479A (en) |
EP (1) | EP0109548B1 (en) |
JP (1) | JPS59134761A (en) |
BR (1) | BR8305869A (en) |
DE (1) | DE3377351D1 (en) |
IT (1) | IT1191046B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0708079B1 (en) * | 1993-07-09 | 1999-04-14 | Kao Corporation | 2-hydroxypropanediamine derivative and detergent composition containing the same |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2935474A (en) * | 1955-11-28 | 1960-05-03 | Visco Products Co | Process of inhibiting corrosion and corrosion inhibiting compositions |
US3400075A (en) * | 1966-11-15 | 1968-09-03 | Union Carbide Corp | Lubricating compositions including a polymer which contains a salt or amide of a diimide |
US3965027A (en) * | 1974-03-11 | 1976-06-22 | Calgon Corporation | Scale inhibition and corrosion inhibition |
DE2558625A1 (en) * | 1975-12-24 | 1977-07-14 | Norte Klessmann & Co Kg | MACHINE TOOL, IN PARTICULAR DRILLING OR MILLING MACHINE |
US4168292A (en) * | 1977-10-26 | 1979-09-18 | Petrolite Corporation | Acylated hydroxyalkylaminoalkylamides and preparation thereof and uses thereof as corrosion inhibitors |
DE3222996A1 (en) * | 1981-06-22 | 1983-03-03 | Basf Ag, 6700 Ludwigshafen | Alkanolamine salts of cyclic amido acids and their use as anticorrosion agents in aqueous systems |
US4374741A (en) * | 1981-07-21 | 1983-02-22 | Cincinnati Milacron Inc. | Polyamide and functional fluid containing same |
-
1982
- 1982-10-25 IT IT23903/82A patent/IT1191046B/en active
-
1983
- 1983-10-19 EP EP83110409A patent/EP0109548B1/en not_active Expired
- 1983-10-19 DE DE8383110409T patent/DE3377351D1/en not_active Expired
- 1983-10-21 US US06/544,800 patent/US4533479A/en not_active Expired - Fee Related
- 1983-10-24 JP JP58197723A patent/JPS59134761A/en active Pending
- 1983-10-24 BR BR8305869A patent/BR8305869A/en unknown
Also Published As
Publication number | Publication date |
---|---|
US4533479A (en) | 1985-08-06 |
EP0109548A1 (en) | 1984-05-30 |
JPS59134761A (en) | 1984-08-02 |
IT8223903A0 (en) | 1982-10-25 |
BR8305869A (en) | 1984-05-29 |
IT1191046B (en) | 1988-02-24 |
DE3377351D1 (en) | 1988-08-18 |
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