DE19756680A1 - Production of fatty acid aminoamide - Google Patents

Abstract

The preparation of fatty acid aminoamides that are dispersible in cold water comprises: (a) reacting triglycerides of 8-22C fatty acids having 0-3 double bonds with polyamines of formula H2N-(CH2)n-NR<2>m-R<1> (I); (b) partially neutralising unreacted amino groups with acid; and (c) adding an alkoxylated ester of formula R<3>O-(C2H4O)p-(C3H6O)q-CO-R<4> (II). R<1> = H, Me, Et, hydroxyethyl or (CH2)nNHR<2>; R<2> = H, Me, Et or hydroxyethyl; n = 2-4; m = 1-4; R<3> = 12-22C alkyl or alkenyl; R<4> = 7-21C alkyl; p = 0-5 and q = 1-5.

Description

The invention relates to a process for the preparation of fatty acid aminoamides improved cold water dispersibility, obtainable by condensation of Fatty acid triglycerides with polyvalent amines, partial neutralization and addition selected dispersion accelerator, as well as the use of the above Fatty acid amino amides as textile treatment agents.

For the treatment of textile fibers, yarns or fabrics, a variety of Compounds or mixtures of substances are proposed to the textiles treated with them impart desired properties or the components of agents for textile care are. Depending on the type of active ingredients used, the Processing properties, the wearing properties of the textiles as well as their care be improved.

For example, the American patent US 2,340,881 describes aqueous Dispersions of condensation products made from a hydroxyalkyl polyamine and a fatty acid glyceride that increases the lubricity and softness of the improve treated textiles.

US 3,454,494 relates to fatty acid condensation products with an additive dispersing polyglycol ethers.  

The German patent DE-PS 19 22 046 describes detergents containing Fatty acid condensation products which are dispersing in their production Contain fatty acid glycerides; in the German patent DE-PS 19 22 047 these are Fabrics also as textile softeners, especially for liquid ones Laundry treatment agent described. These and similar means can be found in Disperse water by placing it in hot water and mostly high shear forces or by making the one that is still melted from the manufacturing process Condensation product dispersed in water. Because of the effort required therefore usually the manufacturer pre-disperses and supplies the user with the Dispersions related to the storage and transportation of significant amounts of water connected and therefore not economically viable.

According to the teaching of German patent applications DE-A 135 30 302, DE-A 137 30 792, DE-A 139 01 820 and DE-A 141 11 648 (Henkel) one can determine the dispersibility such substances by adding suitable dispersion accelerators, for example Glucose, sorbitol, mannitol, pentaerythritol, alkyl polyglucosides, sorbitan esters, gelatin and Improve unsaturated fatty alcohols and fatty acids. Are also established on the market Products used as a dispersion accelerator mixtures of highly ethoxylated tallow alcohols and 1,2-propylene glycol. Furthermore, it is known from DE-A1 43 12 008 that Fatty acid aminoamides to which ethoxylated or propoxylated fatty alcohols have been added will have improved cold water dispersibility.

Nevertheless, it is observed in practice again and again that batches Condensation products of fatty acids and polyvalent amines are obtained, which are found in Do not allow water to disperse, or do so only insufficiently. This uncertainty in view on product quality represents a significant economic disadvantage that the The usability of the substances mentioned as a sought-after textile treatment agent is restricted. Another problem is that even such products of the prior art Technology that has satisfactory dispersibility, as a rule lose irreversibly when stored in the open air.

The object of the invention was therefore to provide fatty acid aminoamides places that are free from the disadvantages described.

The invention relates to fatty acid aminoamides with improved cold water dispersibility, which are obtained by triglycerides of fatty acids having 8 to 22 carbon atoms and 0 or 1 to 3 double bonds with polyamines of the general formula (I)

in which R ^{1 is} hydrogen, a methyl, ethyl, hydroxyethyl or a - (CH ₂ ) _n -NH-R ² - group, R ^{2 is} hydrogen, a methyl, ethyl or hydroxyethyl group, n is a number of 2 to 4 and m represents numbers from 1 to 4, condensed and then partially neutralized unreacted amino groups with acids, characterized in that compounds of the formula (II) are added after the neutralization step,

in which R ^{3 is} an alkyl or alkenyl radical with 12 to 22 carbon atoms and R ^{4 is} an alkyl radical with 7 to 21 carbon atoms and p is 0 or numbers from 1 to 5 and g is a number between 1 and 5.

Surprisingly, it was found that the addition of the selected nonionic Surfactants to the condensation products not only products with one closest prior art leads significantly improved dispersibility, but the condensates have their advantageous properties even after prolonged storage in the air to keep.  

Natural or synthetic glycerides are suitable as starting materials. As Fatty acid components come for example caproic acid, capric acid, caprylic acid, Lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, Oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, Arachic acid, gadoleic acid, behenic acid and erucic acid and their technical Mixtures, such as those that occur during the pressure splitting of fats and oils, in Consideration. Preferably palm oil or tallow is used in hydrogenated form; with these natural triglycerides, the fatty acid part has 16 to 18 carbon atoms and 0 and / or 1 double bond.

The polyamines are preferably derived from optionally hydroxyethyl-substituted From ethylenediamine or diethylenetriamine. Typical examples are Dihydroxyethylene diamine, hydroxyethyldiethylene diamine, hydroxypropyldiethylene triamine and especially aminoethylethanolamine. Also suitable are N, N-dimethyl-1,3- diaminopropane, triethylene tetramine or tetraethylene pentamine.

In view of the application properties of the resulting condensation products, it has proven to be optimal to use polyvalent amines of the formula (I) in which R ¹ for a hydroxyethyl or (CH ₂ ) ₂ NH ₂ group, R ² for hydrogen, n for 2 and m represents 1 or 2.

In the production of the condensation products, for example Fatty acid glycerides and the polyamines in a molar ratio of 0.5: 2.0 to 2.0: 1, preferably 0.7: 1 to 1.5: 1 are used. The components are overheated a period of 0.5 to 5, preferably 1 to 2 hours to a temperature of 80 to 180, preferably 100 to 120 ° C until the fatty acid esters fully or partially implemented are. The mixtures should still be 0.3 to 2.0%, preferably 0.6 to 1.5% basic Contain nitrogen. If the aim is to produce particularly light-colored products, it is recommended that the condensation in the absence of atmospheric oxygen and optionally in the presence of a reducing agent, e.g. B. hypophosphorous acid, perform.  

Following the condensation, the unreacted amino groups are neutralized with low molecular weight organic carboxylic acids, hydroxycarboxylic acids or inorganic acids, such as. B. acetic acid, glycolic acid, lactic acid or phosphoric acid, by, for example, the melt of the condensation product with salt formation mixed with the calculated amount of acid or the amine salt in a solution of the acid forms in water. According to the invention, the acid used for salt formation can be used in such Amounts are used, such as 20 to 80, preferably 30 to 60 mol% Neutralization is required.

Comparatively hydrophobic, nonionic surfactants are used as dispersion accelerators that follow the formula (II). Typical examples are addition products from on average 1 mole of ethylene oxide and 2 moles of propylene oxide, 2 moles of ethylene oxide and 4 Moles of propylene oxide, 5 moles of ethylene oxide and 1 mole of propylene oxide and 2 to 3 moles Propylene oxide on C12 / 18 coconut fatty alcohol, C16 / 18 tallow fatty alcohol, C16 / 18- Palm fat alcohol or oleyl alcohol. These add-on products are subsequently known methods esterified with fatty acids. The fatty acids are selected from the Group of fatty acids with a total of 8 to 22 carbon atoms. Preferably be unbranched, saturated acids are used, for example the capron, caprin, lauric, Myristic or stearic acid.

With regard to the dispersing properties of the resulting products, dispersion accelerators which follow the formula (II) in which R ^{3 stands} for an alkyl radical having 12 to 18 carbon atoms and in which the ratio of p: q in the range of 1: 2 have proven useful to 5: 1. R ⁴ is preferably selected from alkyl radicals having 11 to 17 carbon atoms. Preference is furthermore given to those compounds of the formula (II) in whose synthesis only addition products of propylene oxide are used.

The compounds of formula (II) are the condensation products according to the Neutralization added. The amount used can be 0.5 to 15, preferably 1 to 10 Wt .-%, each based on the condensation products. If desired, can also other known dispersion accelerators, such as Monosaccharides of the aldose and ketose type obtained from this by hydrogenation  derived polyhydroxy compounds, pentaerythritol, trimethylolpropane, alkyl glucosides, Sorbitan esters, polysorbates and hydrophilic polymers based on carbohydrates or unsaturated alcohols or carboxylic acids.

The fatty acid aminoamides produced according to the invention can, for example, in the form made up of powders, scales or pellets and can be easily dissolved in water, Process, especially in cold water, into stable dispersions. This is enough mixing with water and then stirring gently. The received Dispersions are extremely stable and do not tend to separate. You let yourself in the textile sector in various ways for the treatment of fibers, yarns or fabrics use after the exhaust, immersion, padding or spraying process.

Another object of the invention therefore relates to the use of Fatty acid aminoamides which can be prepared according to the invention as a constituent of textile treatment agents. The fatty acid aminoamides can be used in amounts between 10 and 100 wt .-%, preferably 50 to 95 wt .-% may be included.

When using the fatty acid aminoamides according to the invention in Detergents bring about an improved cleaning effect and / or a softening agent the laundry washed with it. The fatty acid aminoamides produced according to the invention can also be used as components of post-treatment agents for washed Textiles are used, which makes the textiles soft and antistatic. The Aftertreatment of the washed textiles can usually be done in the last rinsing bath also done while drying in an automatic clothes dryer, taking one either sprayed the laundry with a dispersion of the agent while drying or by using a flexible, textile fabric that supports the substrate serves. Finally, the fatty acid aminoamides produced according to the invention can be used for Finishing fibers, yarns or fabrics as well as washing textiles as well be used for the after-treatment of washed laundry.

Examples

1452.5 g (1.7 mol) of hydrogenated beef tallow and 176.8 g (1.7 mol) Aminoethylethanolamin mixed and stirred at 120 ° C for about two hours until the residual basic nitrogen content had dropped to 1.05%. The melt was cooled to 90 ° C and neutralized with 85.8 g of a 70 wt .-% glycolic acid. That so Condensation product obtained was with different amounts of an ester added, which is obtainable by reacting 0.5 mol of cetyl / oleyl alcohol with 1 mol Propylene oxide (Dehypon OCP 502, Henkel) and subsequent implementation of this Propylene oxide adducts with 125.0 g technical stearic acid (0.45 mol) at 80 ° C in Presence of 1.2 g of toluenesulfonic acid. Then the product was on a Cooling roller scaled.

Checking the dispersibility Assessment of fine particles

7.5 g of the flaky products (Examples 1a to 1c) were in a 125 ml Pour 92.5 g water (30 ° C, 14 ° d) over the wide-mouth bottle. The bottle was closed, briefly swiveled and stored for 16 h. After swiveling again was over a nutsche, which was colored with a fine-mesh, black Polyamide fabric was occupied, suctioned off at 150 mbar. After drying the fabric was the fine particle size of the residue on a scale from 1 (finely dispersed) to 6 (coarse dispersed, many large lumps) assessed visually.

For comparison, the values were measured for a fatty acid amide without the addition of a Dispersion accelerator of the formula (II) (test V1), and another fatty acid aminoamids not according to the invention, in which instead of the compound of Formula (II) that non-esterified Dehypon OCP 502 was used (test V2). The Amide has always been by reacting hydrogenated beef tallow with aminoethylethanolamine  been made. The approaches are shown in Table 1. The results of the test are summarized in Table 2.

Table 1

Table 2

It can be seen that the fatty acid aminoamides produced according to the invention with regard to their Dispersibility are clearly superior to those without a dispersion accelerator. But even the addition of propoxylated fatty alcohols does not lead to the excellent ones Results obtained when using the fatty acid aminoamides produced according to the invention be achieved.

Claims (8)

1. Process for the preparation of cold water-dispersible fatty acid aminoamides by triglycerides of fatty acids with 8 to 22 carbon atoms and 0 or 1 to 3 double bonds with polyamines of the general formula (I)
in the R ¹ for hydrogen, a methyl, ethyl hydroxyethyl or a (CH ₂ ) _n -NH R ² group, R ² for hydrogen, a methyl, ethyl or hydroxyethyl group, n for numbers from 2 to 4 and m stands for numbers from 1 to 4, condenses and then partially neutralizes unreacted amino groups with acids, characterized in that compounds of the formula (II) are added after the neutralization,
in which R ^{3 is} an alkyl or alkenyl radical with 12 to 22 carbon atoms and R ^{4 is} an alkyl radical with 7 to 21 carbon atoms and p is 0 or numbers from 1 to 5 and q is a number between 1 and 5. 2. The method according to claim 1, characterized in that triglycerides saturated Fatty acids with 12 to 18 carbon atoms can be used. 3. The method according to any one of claims 1 or 2, characterized in that polyamines of the general formula (1) are used in which R ¹ for a hydroxyethyl or (CH ₂ ) ₂ -NH ₂ group, R ² for hydrogen, n stands for 2 and m stands for 1 or 2. 4. The method according to any one of claims 1 to 3, characterized in that the Triglycerides and the polyamines of formula (I) in a molar ratio of 0.5: 2.0 to 2.0: 1 can be condensed. 5. Process according to claims 1 to 4, characterized in that the neutralized unreacted amino groups to 20 to 80 mol%. 6. The method according to claims 1 to 5, characterized in that the Compounds of formula (II) in amounts of 0.5 to 10 wt .-%, preferably 1.0 to 5.0% by weight, based on the condensation product, is added. 7. The method according to any one of claims 1 to 6, characterized in that one Use compounds of formula (II) in which p is 0 and g is a number between 1 and 5 means. 8. Use of fatty acid aminoamides according to claim 1 as a textile treatment medium.