SK280381B6 - Alkyl succinic acid derivatives as metal working agents and method of their preparation - Google Patents

Abstract

The present invention relates to succinic acid derivatives, i.e. salts of alkenylsuccinic acid alkoxyalkyl-N-substituted amides, N,N-disubstituted 2-amino ethylesters of alkenylsuccinic acid and/or alkenylsuccinic acid imides, a method of their preparation, preparations for the treatment of metals which contain said substances and their use as auxiliaries for treating metals, in particular as preservative agents against corrosion and as emulsifiers for aqueous and oil preparations.

Description

Technical field

The present invention relates to succinic acid derivatives, namely salts of N-substituted alkenylsuccinic amides, Ν, dis-disubstituted 2-amino ethyl esters of alkenylsuccinic acid and / or alkenylsuccinic acid imides, a process for their preparation, metalworking preparations containing said substances and their use as auxiliaries. metalworking agents, in particular as corrosion protection agents and as emulsifiers in aqueous and oily preparations.

BACKGROUND OF THE INVENTION

The use of metal processing aids is directed to the various metal pretreatment and finishing processes. The working area includes the shaving and shearless forming of metal parts. Drilling and cutting oils are used for metal chip forming, rolling and drawing oils are used for chipless metal forming.

Corrosion protection agents and emulsifiers in emulsifiable metal working fluids should meet the following requirements:

1. outstanding anti-corrosion properties against ferrous metals;

2. ability to emulsify against mineral oils, optionally also in combination with a selected non-ionic compound;

3. slight foaming tendency or rapid foam decomposition;

4. inhibiting the growth of microorganisms.

The above-mentioned requirements are only partially met by the known compounds. EP-A-127 132 discloses salts of N-substituted C ₆ -C 6 -alkenylsuccinic amides and their use as corrosion protection agents. However, these compounds have no emulsifying properties, which leads to undesired downtimes in the emulsions used. In addition, emulsions with these compounds tend to foam, which is particularly disadvantageous in working processes such as grinding, as the emulsions are subject to high mechanical stress.

DE-A-33 00 874 describes alkanolamine salts of N-substituted C ₆ -C ₁₈ -alkenylsuccinic amides in which a primary amine having an alkyl chain of 1 to 10 carbon atoms is used to form the N-substituted amide.

DE-A-33 41 013 describes N-substituted C ₆ -C ₁₈ -alkenylsuccinic amides in which secondary amines of 1 to 10 carbon atoms were used for the N-substituted amidation.

Also, using these compounds, these requirements cannot be met.

SUMMARY OF THE INVENTION

It is an object of the present invention to provide alkenylsuccinic acid derivatives having the claimed properties.

Surprisingly, it has been found that this task can be solved by using salts of N-substituted alkenylsuccinic amides containing alkoxylamines as the amine component, optionally in admixture with salts of Ν, dis-disubstituted alkenylsuccinic acid esters containing alkoxylamine as ester group, and acid imides alkenylsuccinic.

The present invention provides salts of alkoxyalkyl-N-substituted alkenylsuccinic amides of formula (Ia) and / or (Ib)

R1-CH-CO-NHR1 R1-CH-COO-M +

I (la)

CH ₂ -COO-M ⁺ CH 2 -CH-NHR 2 optionally in admixture with salts of Ν, Ν-disubstituted 2-amino ethyl succinates of general formula (IIa) and / or (IIb)

R1-CH-COO-CHR ⁴ -CH ₂ + R ⁵ R ^e R1-CH-COOM ···

I (Ila)

CH 2 -COOM * CH ₂ -COO-CHR ⁴ -CH 2 -NR ⁵ R ^e and / or alkenylsuccinic acid imides of formula (III) r-1-ch-co)

I NR ² (H1),

ch ₂ -what

R ¹ represents a C 6 -C 30 alkenyl or C 6 -C 30 alkyl group, preferably a C 9 -C 18 alkenyl or C 9 -C 18 alkyl group, which groups may be straight or branched,

R ² is - _{(CH2) n-O-} (A) _m -R ^3, wherein

A is -CH ₂ -CH ₂ -O- or -CH (R ⁴ ) -CH ₂ -O-, R ⁵ is C 1 -C 18 alkyl, which may be straight or branched, R ⁴ is hydrogen or methyl, n is 1 to 6, m is 0 to 8,

M ⁺ means an alkali metal or alkaline earth metal cation or an ammonium ion of the formula HNR ^S R ⁶ R ⁷ and

R 1, R ⁶ and R ⁷ may be the same or different and represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms, in particular a 2-hydroxyethyl group and a 2-hydroxypropyl group.

Salts of Ν, Ν-disubstituted 2-amino ethyl esters of alkenylsuccinic acid of formulas (IIa), (IIb) and alkenylsuccinic acid imides of formula (III) may occur as by-products in the preparation of N-substituted alkenylsuccinic acid amides of formula (Ia) and (Ib) and are usually present in a concentration of 0 to 40% by weight, preferably 0 to 20% by weight, in admixture with alkoxyalkyl-N-substituted alkenylsuccinic acid amides of formula (Ia) and (1b).

The present invention also relates to a process for the preparation of salts of alkoxyalkyl-N-substituted alkenylsuccinic amides of formula (Ia) and / or (Ib), optionally in admixture with salts of Ν, dis-disubstituted 2-amino ethyl esters of alkenylsuccinic acid of formula (IIa) and and / or (IIb) and / or alkenylsuccinic acid imides of formula (III), characterized in that alkenylsuccinic anhydrides are reacted with alkoxyalkylamines of formula (IV)

H ₂ N- (CH ₂ ) _n -O- (A) _m -R ³ (IV) wherein

R ³ represents an alkyl group having 1 to 18 carbon atoms which may be straight or branched, n represents a number from 1 to 6 and m represents a number from 0 to 8, wherein

A is as defined above, in a molar ratio of 1: 0.7 to 2.5, preferably 1: 0.8 to 1.2, at a temperature in the range of 20 to 120 ° C, preferably 60 to 100 ° C, and this reaction is The reaction is carried out in the presence of a base which is in an equimolar amount to the alkoxyalkylamine of formula (IV) or a base in an equimolar amount to the alkoxyamine of the formula (IV) is added following the reaction.

The bases used are alkali metal hydroxides, alkaline earth metal hydroxides, alkanolamines of the formula NR ⁵ R ⁶ R ⁷ or mixtures thereof.

Typically, bases are used in equimolar amounts to alkanolamines.

The production of the alkenylsuccinic anhydride used as the starting material is carried out by reaction of olefins and maleic anhydride and is known. Preferred olefins are oligomers of ethylene, propylene and butylene, as well as olefins with an internally bonded. For example, n-dodecylsuccinic anhydride can be prepared by reacting n-dodecene with maleic anhydride at a temperature in the range of 150 to 230 ° C, at a pressure in the range of 0.3 to 1.0 MPa and in the presence of a suitable radical inhibitor. The alkenyl (succinic acid anhydrides) thus obtained can be used either after purification by distillation or crystallization, or also directly for the preparation of the compounds according to the invention.

Alkoxyalkylamines, for example 2-hydroxyethylamine, can be prepared by the addition of acrylonitrile to alcohols and subsequent hydrogenation.

The alkoxyalkyl-N-substituted alkenylsuccinic amide salts of the present invention of formulas (Ia) and / or (Ib), optionally in admixture with the salts of the Ν, dis-disubstituted 2-amino ethyl esters of alkenylsuccinic acid of formula (IIa) and / or (IIb) , and / or alkenylsuccinic acid imides of the formula (III) can be used as metal processing aids, in particular as corrosion protection agents and as emulsifiers in aqueous and / or oil-containing preparations or metalworking fluids.

The present invention also relates to metalworking compositions containing water and / or oil, in particular for use as cooling lubricants, characterized in that they contain said alkoxyalkyl-N-substituted alkenylsuccinic amide salts of the formula (Ia) and / or ( Ib), optionally in admixture with the salts of Ν, Ν-disubstituted 2-amino ethyl esters of alkenylsuccinic acid of formula (IIa) and / or (IIb), and / or alkenylsuccinic acid imides of formula (III).

Salts of N-substituted alkenylsuccinic acid amides of formula (Ia) and / or (Ib), optionally in admixture with salts of Ν, dis-disubstituted 2-amino ethyl esters of alkenylsuccinic acid of formula (IIa) and / or (IIb), and / or The alkenylsuccinic acid imides of the general formula (III) produced by the process according to the invention form clear solutions in water and give easily emulsifiable preparations with mineral oil in water. The compounds are used in concentrated form as emulsifiers and anticorrosive agents in oily and / or aqueous preparations. Concentration of salts of alkoxyalkyl-N-substituted alkenylsuccinic amides of formula (Ia) and / or (Ib), optionally in admixture with salts of Ν, dis-disubstituted 2-amino ethyl esters of alkenylsuccinic acid of formula (IIa) and / or (IIb) , and / or alkenylsuccinic acid imides of formula (III) is higher in the formulations than in use and is usually 10 to 80% by weight. Chip and shamless formulations, such as drilling, cutting, drawing and rolling fluids, are diluted with water.

To produce the preparations, the products of the present invention are either mixed in water in the required amount or mixed with mineral oil or a mixture of mineral oil and water. The aqueous or oily preparations obtained are usually diluted or emulsified with water before use. The dilution ratio is generally 1: 10 to 1: 100. The concentration of salts of alkoxyalkyl-N-substituted alkenylsuccinic amides in metal working fluids, e.g., drilling fluids, cutting fluids, drawing fluids and rolling fluids, is generally about 0.1 to 10% by weight, preferably 2 to 10% by weight. The concentrations indicated for the treatment of metals refer both to the use of the products in water and to the mineral oil / water emulsions. The term metal working fluids also includes cooling lubricants.

Salts of alkoxyalkyl-N-substituted alkenylsuccinic amides are used in aqueous metalworking fluids containing mineral oils as corrosion protection emulsifier and in aqueous, oil-free metalworking fluids as corrosion protection agent.

They are suitable for mixing with conventional mineral oils, in particular with naphthenic base, paraffin base and mixed base mineral oils. The metalworking compositions or fluids may contain additional auxiliaries to optimize emulsifying properties and corrosion protection. To this end, oxetlates of the general formula (V) are particularly preferably used.

R ⁸ -O- (CH ₂ -CH ₂ -O) _p H (V) wherein

R ⁸ represents an alkyl group having 10 to 22 carbon atoms, an alkenyl group having 10 to 22 carbon atoms or an alkylphenyl group having a total of 10 to 20 carbon atoms, and p is a number of 2 to 10.

Fatty acid alkanolamides of the general formula (VI) are also used as excipients.

R ⁹ -CO-NR ¹⁰ R (VI) wherein

R ⁹ represents an alkyl group having 10 to 22 carbon atoms or an alkenyl group having 10 to 22 carbon atoms, and

R ¹⁰ and R ¹¹ are the same or different and represent a hydroxyalkyl group having 1 to 6 carbon atoms, in particular a 2-hydroxyethyl group or a 2-hydroxypropyl group.

Other suitable excipients are the ether carboxylic acids of formula (VII)

R ^{L 2} - (O-CH 2 CH 2) q [O-CH (R ¹⁾ _{r -CH2} -CH2J COO'X ⁺ (VII), wherein

R ¹² represents a branched or straight, saturated or unsaturated alkyl or alkenyl group having in each case 8 to 22 carbon atoms, q and r may independently be 0 to 10, provided that the sum of q and j is at least 1, and

X represents a hydrogen atom, an alkali metal atom or an alkaline earth metal atom.

Also suitable adjuvants are alkoxylated primary amines of formula (VIII)

R ¹³ -N [(-OCH ₂ -O) _p H] _u (VIII) wherein

R ¹³ represents an alkyl or alkenyl group having 12 to 20 carbon atoms, preferably an alkyl group having 16 to 18 carbon atoms, p represents a number of 2 to 10, preferably 4 to 6, and u is a number of 1 or 2, one, there is a hydrogen atom on the free bond of the nitrogen atom.

Other suitable excipients are also polyglycol esters of fatty acids, in particular saturated or unsaturated fatty acids having 10 to 22 carbon atoms in the alkyl chain and having 1 to 10 ethylene oxide units, such as oleic acid with 4 to 6 ethylene oxide units.

Said excipients are contained in the compositions individually or in mixtures in general in an amount of about 20 to 40% by weight. In addition, customary additives such as antifoams or suitable preservatives may also be present in the formulations.

The quantities used to characterize the compositions, such as acid number, amine number, basic nitrogen and iodine number, are determined by the following methods:

Determination of acid number

To determine the acid value, given in mg KOH / g of substance, weigh 0,1 to 0,5 g of the sample into a 150 ml beaker, dissolve in 60 to 80 ml ethyl alcohol and titrate with 0,1 N ethanolic potassium hydroxide solution. The equivalence point is determined potentiometrically (instruments: Methrom Titroprozessor 682, Dozimat 665 with a combined glass pH electrode).

Determination of basic nitrogen and amine number

For the determination of basic nitrogen, expressed in% N, weigh 0,1 to 0,5 g of the sample into a 150 ml beaker, dissolve in 60 to 80 ml glacial acetic acid and titrate with 0,1 N perchloric acid in glacial acetic acid . The equivalence point is determined potentiometrically (instruments: Methrom Titroprozessor 682, Dozimat 665 with a combined glass pH electrode).

The amine number, expressed in mg KOH / g of substance, is calculated from the basic nitrogen value according to the formula: amine number [mg KOH / g] =% basic nitrogen. .5,61 / 0.140067

Determination of iodine number

The iodine value for color is the concentration of free iodine in the iodine iodide solution (in mg of iodine per 100 ml of iodine iodide solution) and is used to indicate the color and / or light transmission through the solution and similar liquids. The basis for the determination of the iodine number is the iodine color scale (comparison tubes), this determination being carried out in accordance with DIN 53403.

DETAILED DESCRIPTION OF THE INVENTION

The following examples serve to illustrate the invention without limiting it.

Example 1

Preparation of the triethylammonium salt of _C12 / _14- alkenylsuccinic acid 3-butoxypropyl-N-substituted amide

A 1 liter three-necked flask equipped with a stirrer, an internal thermometer and a reflux condenser was charged with a mixture of 127.5 g (1.0 mol) of 3-n-butoxypropylamine, 149.1 g (1.0 mol) of triethanolamine and 30 g of water. 0.5 hours, fed 279.2 g (saponification value: 401.9 mg KOH / g; 1 mole) of technical anhydride, a C _{2 R] 4} -alkenyljantárovej (chain distribution of the olefin feed 65% by weight of dodecene, tetradecene 35%) whereby an exothermic reaction occurs. The internal temperature is maintained by temporary cooling to a maximum of 50 ° C. After the addition was complete, the reaction mixture was stirred for 2 hours at 50 ° C. The reaction mixture contains about 67% by weight of the triethylammonium- / 3-butoxypropylammonium salt of _C12 / _14- alkenylsuccinic acid 3-n-butoxypropyl-N-substituted amide and about 33% by weight of 3-n-butoxypropylammonium at this time. - triethanolammonium salt of the triethanolamine ester of the C 1 acid ₂ / | _4- alkenes (amber (as determined by basic nitrogen).

The reaction mixture was then basified by the addition of 48 g (0.6 mol) of 50% sodium hydroxide. 642.1 g of a tan solid having an iodine color number of 30 to 40, an amine number (determined by potentiometry) of 171 mg KOH / g, an acid number of 46 mg KOH / g and a viscosity are obtained.

1.9 Pa.s (Brookfield, 28 ° C, 10L / min).

Example 2

Preparation of the triethanolammonium salt of _C12 / _14- alkenylsuccinic acid 3-methoxypropyl-N-substituted amide

The apparatus described in Example 1 is charged with 44.6 g (0.5 mol) of 3-methoxypropylamine at 30 ° C and 139.6 g (saponification number) is added dropwise over 30 minutes.

401.9 mg KOH / g 0.5 mol) of C, γ-4-alkenes anhydride (chain separation with olefin mixture: 65% dodecene, 35% tetradecene), while exothermic reaction. The reaction mixture is stirred for 2 hours at 50 ° C (conversion by basic nitrogen control> 98%) and then neutralized by the addition of 74.5 g M (0.5 mol). The reaction mixture was then basified by the addition of 39 g of 30% sodium hydroxide solution (pH value of 1% solution in demineralized water: 8.4) to give 296 g of a dark yellow liquid with an iodine color number of 20, (amine number determined potentiometrically). 151 mg KOH / g and an acid number of 50.6 mg KOH / g.

Example 3

Production of the 3-metyldietanolamóniovej butoxypropylamidu of C | 2 _{/] 4} -alkenyljantárovcj

To a mixture of 25.5 g (0.2 mol) of 3-butoxypropylamine, 23.8 g (0.2 mol) of N-methyl-diethanolamine and 6 g of demineralized water is initially added dropwise over 30 minutes at 30 ° C. 8 g (0.2 g) of technical anhydride nC _I2 / I4-alkenylsuccinic the exothermic reaction, the reaction temperature is maintained by temporarily cooling to 50 DEG C., and the reaction mixture was stirred for a further 2 hours at ° C. At this point, the reaction mixture contained about 86% by weight of the triethylammonium- (3-butoxypropylammonium salt of 3-butoxypropyl-N-substituted acid amide nC j ₂ ) according to basic nitrogen analysis. ₄ -alkenes (succinic and about 14% by weight of 3-butoxypropylamónium- / triethanolamine salt of triethanolamine nC | _2/14 -alkenes (amber. After the reaction, the mixture was made basic with 9.6 g 50% NaOH to give the following 119.1 g of a yellowish viscous liquid having an iodine color number of 20, an amine number of 168 mg KOH / g and an acid number of 51 mg KOH / g.

Example 4

Preparation of the triethanolammonium salt of C12-14-alkenylsuccinic acid 3-methoxypropylamide

To 139.8 g (0.5 mol) of C1-4-alkenylsuccinic anhydride, 3-methoxypropylamine is added dropwise over 0.5 hours while the internal temperature does not exceed 50 ° C, the reaction mixture is allowed to stir for one hour. and then neutralized with a mixture of 75.6 g of triethanolamine and 14.2 g of water. After one hour of reaction, the reaction mixture was obtained with a N-substituted amide / ester ratio of 93: 7 (analysis over basic nitrogen). After alkalization with 24 g of 50% sodium hydroxide, 291.6 g of a brownish-yellow liquid having an amine number of 160 mg KOH / g and a viscosity of 2.3 Pa.s. are obtained.

Example 5

Production of the triethanolammonium salt of tripropylsuccinic acid 3-methoxypropylamide

To a mixture of 44.6 g (0.5 mol) of 3-methoxypropylamine, 74.5 g (0.5 mol) of triethanolamine and 13.6 g of water is added dropwise at an initial temperature of 30 ° C over 30 minutes and with temporary cooling. 1.5 g (0.5 mol) of technical tripropenylsuccinic anhydride such that the internal temperature does not exceed 50 ° C. The reaction mixture is stirred for 2 hours at this temperature, after which time a mixture containing 63% by weight of the N-substituted amide and 37% by weight of the Ν, Ν-disubstituted 2-amino ethyl ester is obtained. Basification with 24 g of 50% sodium hydroxide gives 266.2 g of a sweet yellow viscous liquid having an amine number of 206 mg KOH / g and an acid number of 56 mg KOH / g.

The following table lists the performance characteristics of alkenylsuccinic acid 3-alkoxypropylamides.

table

Example 5 2 3 4 5

Appearance of 3% aqueous solution e deat. water immediately limpid English Translation: limpid limpid po 24 h tlry transp.čfry limpid limpid Foam height ¹ ): immediately > 50 > 50> 50 > 50 > 50 after S min > 50 > 50> 50 20 12 20 * dH immediately limpid transp. limpid limpid turbidity. po 24 h limpid transp. limpid limpid za kal. Foam height ¹ ): Immediately > 50 50> 50 > 50 45 after 5 min 3 45> 50 Tracks 2 the edge. foam Corrosion protection a) Herbert test (DIN 51350/1) dest water t, 0% RO / FR RO / FR RO / FR RO / FR RO / FR 20 * dH 3.0% RO / FR RO / FR RO / FR RO / FR RO / FR (b) paper filter test (DIN 51360/2) dest. water 1.5% 0 1 ABOUT 0 1 20 * dH 3.0% ABOUT 0 0 O 0 Emulgovatefnosť Spörr. buckle. buckle. sport sporrt.

Explanation to the table:

¹¹ To determine the behavior of the foam can with 50 ml of 3% aqueous solution of the product under examination in a 100 ml graduated cylinder with a scale, the sealed glass cover 20x and the strongly shaken in the horizontal direction. The determination is made after the indicated waiting times by measuring the amount of foam in ml.

Test data:

Preparations consisting of:

% by weight% by weight% by weight% by weight emulsifier mixture nonylphenol ethoxylate water naphthenic base mineral oil.

Emulsifier mixture:

% by weight% by weight product by examples oleyl alcohol + 2EO (ethylene oxide) diethanolamide of talic acid

Claims (14)

PATENT CLAIMS 1. Alkylsuccinic acid derivatives of the general formula (Ia) and / or (Ib) R1-CHCO-NHR ² R'-CH-100-M * I (Ia) I (Ib), ch ₂ -coo-m + ch ₂ -ch-nhr 2 optionally in admixture with salts of Ν, Ν-disubstituted 2-amino ethyl succinates of formula (IIa) and / or (IIb) R 1 -CH-COO-CHR 4 -CH ₂ -NR 5 R 6 R 1 -CH-COO-M + I (lla) CH 2 -COO-M-COO-CHI-CHI-CHR-NRSR ⁶ and / or alkenylsuccinic acid imides of the formula (III) R ¹ -CH-CO \ I NR ² (III), CH2-CO in which R ¹ represents a C 6 -C 30 alkenyl or C 6 -C 30 alkyl group, preferably a C 9 -C 18 alkenyl or C 9 -C 18 alkyl group, which groups may be straight or branched, R ² is - _{(CH2) n-O-} (A) _m -R ^3, wherein A is -CH ₂ -CH ₂ -O- or -CH (R ⁴ ) -CH ₂ -O-, R ³ is C 1 -C 18 alkyl which may be straight or branched, R ⁴ represents hydrogen or methyl, n is 1-6, m is 0-8, M ⁺ means an alkali metal or alkaline earth metal cation or an ammonium ion of the formula HNR ^S R ⁶ R ⁷ and R ⁵ , R ⁶ and R ⁷ may be the same or different and represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms, in particular a 2-hydroxyethyl group and a 2-hydroxypropyl group. Compounds according to claim 1, characterized in that the salts of Ν, Ν-disubstituted 2-amino ethyl esters of alkenylsuccinic acid of the formulas (IIa), (IIb) and alkenylsuccinic acid imides of the formula (III) are present in a concentration of up to 40%. % by weight, preferably up to 20% by weight, in admixture with salts of alkoxyalkyl-N-substituted alkenylsuccinic acid amides of formula (Ia) and / or (1b). A process for the preparation of alkoxyalkyl-N-substituted alkenylsuccinic acid amides of formula (Ia) and / or (1b), optionally in admixture with the salts of N, N-disubstituted 2-amino alkenylsuccinic acid esters of formula (IIa) and / or ( IIb), and / or alkenylsuccinic acid imides of formula (III), characterized in that alkenylsuccinic anhydrides are reacted with alkoxyalkylamines of formula (IV) H ₂ N- (CH ₂ ) _n -O- (A) _m -R ³ (IV) wherein R ³ represents an alkyl group having 1 to 18 carbon atoms which may be straight or branched, n represents a number from 1 to 6 and m represents a number from 0 to 8, wherein A is as defined above, in a molar ratio of 1: 0.7 to 2.5, preferably 1: 0.8 to 1.2, at a temperature in the range of 20 to 120 ° C, preferably 60 to 100 ° C, and this reaction is is carried out in the presence of a base which is in an equimolar amount to the alkoxyalkylamine of formula (IV), or a base in an equimolar amount to the alkoxyamine of the formula (IV) is added following the reaction. The process according to claim 3, characterized in that the bases used are alkali metal hydroxides, alkaline earth metal hydroxides, alkanolamines of the formula NR ⁵ R ⁶ R ⁷ , in which the substituents are as defined above, or mixtures thereof. Process according to Claim 3, characterized in that 2-hydroxyethylamine and / or 2-hydroxypropylamine is used as alkoxyalkylamine of the general formula (IV). Metalworking preparations containing water and / or oil, in particular for use as cooling lubricants, characterized in that they contain salts of alkoxyalkyl-N-substituted alkenylsuccinic acid amides of the general formula (Ia) and / or (1b), optionally in admixture with the salts of the Ν, dis-disubstituted 2-amino ethyl esters of alkenylsuccinic acid of formula (IIa) and / or (IIb), and / or alkenylsuccinic acid imides of formula (III) according to claim 1. Formulations according to claim 6, characterized in that they contain the compounds according to claim 1 in a concentration of 10 to 80% by weight. 8. Metal working liquids containing water and / or oil, in particular for use as cooling lubricants, characterized in that they contain salts of alkoxyalkyl-N-substituted alkenylsuccinic acid amides of the general formula (Ia) and / or (1b), optionally in mixtures with salts of the Ν, Ν-disubstituted 2-amino ethyl esters of alkenylsuccinic acid of formula (IIa) and / or (IIb), and / or alkenylsuccinic acid imides of formula (III) according to claim 1. 9. Metalworking fluids containing water and / or oil according to claim 8, characterized in that they contain the compounds according to claim 1 in a concentration of 0.1 to 10% by weight, preferably 2 to 10% by weight. Formulations according to claim 6, characterized in that they contain as auxiliary substances oxethylates of the general formula (V) R ⁸ -O- (CH ₂ -CH ₂ -O) _P H (V) wherein R ⁸ is C 10 -C 22 alkyl, C 10 -C 22 alkenyl or C 10 -C 20 alkylphenyl and p is 2 to 10, and / or fatty acid alkanolamides of formula (VI) R ⁹ -CO-NR ¹⁰ R (VI) wherein R ⁹ represents an alkyl group having 10 to 22 carbon atoms or an alkenyl group having 10 to 22 carbon atoms, and ^{R, o} and R ¹¹ are identical or different and is a hydroxyalkyl group having 1 to 6 carbon atoms, especially 2-hydroxyethyl or 2-hydroxypropyl, and / or ether carboxylic acid of formula (VII) R ¹² - (O-CH ₂ -CH ₂ ) _q - [O-CH (R ') - CH ₂ ] _r -CH ₂ COOX ⁺ (VII) in which R ¹² represents a branched or straight, saturated or unsaturated alkyl or alkenyl group having in each case 8 to 22 carbon atoms, q and r may independently be 0 to 10, provided that the sum of q and r is at least 1, and X represents a hydrogen atom, an alkali metal atom or an alkaline earth metal atom, and / or alkoxylated primary amines of formula (VIII) R ¹³ -N [(-OCH ₂ -O) _p H] _u (VIII) wherein R ¹³ represents an alkyl or alkenyl group having 12 to 20 carbon atoms, preferably an alkyl group having 16 to 18 carbon atoms, p represents a number of 2 to 10, preferably 4 to 6, and u is a number of 1 or 2, provided that u is one, there is a hydrogen atom on the free bond of the nitrogen atom, and / or polyglycol esters of fatty acids, especially saturated or unsaturated fatty acids having 10 to 22 carbon atoms in the alkyl chain and 1 to 10 ethylene oxide units, preferably oleic acid with 4 to 6 ethylene oxide units . Formulations according to claim 10, characterized in that the excipients are present in a concentration of 20 to 40% by weight. Formulations according to claim 6, characterized in that they comprise a defoamer and / or a preservative. Metal processing fluids according to claim 8, characterized in that they contain as additional auxiliaries oxethylates of the general formula (V) R ⁸ -O- (CH ₂ -CH ₂ -O) _p H (V) wherein SK 280381-6 ^R is alkyl having 10 to 22 carbon atoms, alkenyl having 10 to 22 carbon atoms or alkylphenyl having a total of from 10 to 20 carbon atoms and p is a number from 2 to 10, and / or a fatty acid alkanolamide of the formula (VI) R ⁹ -CO-NR 10 R (VI) in which R ⁹ represents an alkyl group having 10 to 22 carbon atoms or an alkenyl group having 10 to 22 carbon atoms, and R ¹⁰ and R ¹¹ are the same or different and represent hydroxyalkyl having 1 to 6 carbon atoms, in particular 2-hydroxyethyl or 2-hydroxypropyl, and / or ether carboxylic acids of the general formula (VII) R ¹² - (O-CH 2 -CH 2) q - [O-CH (R ¹ ) -CH 2] _r -CH ₂ COOX ⁺ (VII) in which R ¹² represents a branched or straight, saturated or unsaturated alkyl or alkenyl group having in each case 8 to 22 carbon atoms, q and r may independently be 0 to 10, provided that the sum of q and r is at least 1, and X represents a hydrogen atom, an alkali metal atom or an alkaline earth metal atom, and / or alkoxylated primary amines of formula (VIII) R ¹³ -N [(-OCH ₂ -O) _p II] _u (VIII), wherein R ¹³ represents an alkyl or alkenyl group having 12 to 20 carbon atoms, preferably an alkyl group having 16 to 18 carbon atoms, p represents a number of 2 to 10, preferably 4 to 6, and u is a number of 1 or 2, provided that u is one, there is a hydrogen atom at the free bond of the nitrogen atom, and / or polyglycol esters of fatty acids, especially saturated or unsaturated fatty acids having 10 to 22 carbon atoms in the alkyl chain and having 1 to 10 ethylene oxide units, preferably oleic acid with 4 to 6 ethylene oxide units . Use of salts of alkoxyalkyl-N-substituted alkenylsuccinic acid amides of formula (Ia) and / or (Ib), optionally in admixture with salts of N, N-disubstituted 2-amino ethyl esters of alkenylsuccinic acid of formula (IIa) and / or (IIb) and / or alkenylsuccinic acid imides of the general formula (III) as metal processing aids, in particular as corrosion protective agents and emulsifiers in aqueous and / or oil-containing preparations or metal processing aids.