WO1999032432A1 - Fatty acid aminoamides with improved dispersibility - Google Patents

Abstract

The invention relates to fatty acid aminoamides which are obtained by condensing fatty acids or the esters thereof with multivalent amines, by partially neutralising unreacted amino groups with acids and by adding dispersion promoters of formula (II), wherein R<3> is an alkyl or alkenyl radical with 12-22 carbon atoms and R<4> is an alkyl radical with 7-21 carbon atoms, p represents 0 or 1-5 and q represents a number between 1 and 5.

Description

FATTY ACID AMINOAMIDES WITH IMPROVED DISPERSIBILITY

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

For the treatment of textile fibers, yarns or fabrics, a large number of compounds or mixtures of substances are proposed which impart the desired properties to the textiles treated therewith or which are components of agents for textile care. Depending on the type of active ingredients used, the processing properties, the wearing properties of the textiles and their care can be improved.

For example, US Pat. No. 2,340,881 describes aqueous dispersions of condensation products, made from a hydroxyalkyl polyamine and a fatty acid glyceride, which improve the lubricity and the softness of the textiles treated with them.

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

The German patent DE-PS 19 22 046 describes detergents containing fatty acid condensation products which contain fatty acid glycerides with a dispersing action; in the German patent DE-PS 19 22 047 these are Fabrics also as textile softeners for especially liquid ones

Laundry treatment agent described. These and similar agents can be dispersed in water by placing them in hot water and usually applying high shear forces, or by dispersing the condensation product, which has still been melted, in water. Because of the effort required, the manufacturer usually carries out the dispersion and supplies the user with the dispersions, which is associated with the storage and transport of considerable amounts of water and is therefore not economically viable.

According to the teaching of German patent applications DE-Al 35 30 302, DE-Al 37 30 792, DE-Al 39 01 820 and DE-Al 41 11 648 (Henkel), the dispersibility of such substances can be increased by adding suitable dispersion accelerators, for example glucose , Sorbitol, mannitol, pentaerythritol, alkyl polyglucosides, sorbitan esters, gelatin and unsaturated fatty alcohols and fatty acids. Products are also established on the market that contain mixtures of highly ethoxylated tallow alcohols and 1,2-propylene glycol as dispersion accelerators. It is also known from DE-Al 43 12 008 that fatty acid aminoamides, to which ethoxylated or propoxylated fatty alcohols are added, have improved cold water dispersibility.

Nevertheless, it is repeatedly observed in practice that batches of condensation products of fatty acids and polyvalent amines are obtained which cannot be dispersed in water or can only be insufficiently dispersed. This uncertainty with regard to product quality represents a considerable economic disadvantage that limits the usability of the substances mentioned as a sought-after textile treatment agent. Another problem is also that even such prior art products that have satisfactory dispersibility tend to irreversibly lose them when stored in air.

The object of the invention was therefore to provide fatty acid aminoamides which 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)

R ²

H ₂ N - [(CH ₂ ) _n N] _m -R ¹ (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 stands for 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,

O

R ³ O- (C ₂ H ₄ O) _p - (C ₃ H ₆ O) _q -CR ⁴ (II)

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.

Surprisingly, it was found that the addition of the selected nonionic surfactants to the condensation products not only results in products with a dispersibility which is significantly improved compared to the closest prior art, but that the condensates retain their advantageous properties even in the event of prolonged storage in the air.

Natural or synthetic glycerides are suitable as starting materials. Examples of fatty acid components are 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, arachidic acid, gadoleic acid, behenic acid and erucic acid as well as their technical mixtures as they occur, for example, in the pressure splitting of fats and oils . Preferably palm oil or tallow is used in hydrogenated form; in 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 ethylenediamine or diethylenetriamine. Typical examples are dihydroxyethylene diamine, hydroxyethyldiethylene diamine, hydroxypropyldiethylene triamine and in particular aminoethylethanolamine. N, N-Dimethy 1-1,3-diaminopropane, triethylene tetramine or tetraethylene pentamine are also suitable.

In view of the performance 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 stands for 2 and m stands for 1 or 2.

In the production of the condensation products, for example the fatty acid glycerides and the polyamines can be used in a molar ratio of 0.5: 2.0 to 2.0: 1, preferably 0.7: 1 to 1.5: 1. The components are heated over 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 have been completely or partially reacted. The mixtures should still contain 0.3 to 2.0%, preferably 0.6 to 1.5% basic nitrogen. If the production of particularly light-colored products is desired, it is advisable to condense in the absence of atmospheric oxygen and, if appropriate, in the presence of a reducing agent, e.g. B. hypophosphorous acid to perform. Following the condensation, the unreacted amino groups are neutralized with low molecular weight organic carboxylic acids, hydroxycarboxylic acids or inorganic acids, such as. As acetic acid, glycolic acid, lactic acid or phosphoric acid, for example by mixing the melt of the condensation product with the calculated amount of acid with salt formation or forming the amine salt in a solution of the acid in water. According to the invention, the acid used for salt formation can be used in amounts such as are required for 20 to 80, preferably 30 to 60, mol% neutralization.

Comparatively hydrophobic, nonionic surfactants which follow the formula (II) are suitable as dispersion accelerators. Typical examples are addition products of an average of 1 mol of ethylene oxide and 2 mol of propylene oxide, 2 mol of ethylene oxide and 4 mol of propylene oxide, 5 mol of ethylene oxide and 1 mol of propylene oxide and 2 to 3 mol of propylene oxide with C 12/18 coconut oil alcohol, C16 / 18 tallow fatty alcohol, C16 / 18- Palm fat alcohol or oleyl alcohol. These addition products are then esterified with fatty acids using known methods. The fatty acids are selected from the group of fatty acids with a total of 8 to 22 carbon atoms. Unbranched, saturated acids are preferably used, for example caproic, capric, 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 represents} 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 added to the condensation products after neutralization. The amount used can be 0.5 to 15, preferably 1 to 10,% by weight, based in each case on the condensation products. If desired, other known dispersion accelerators, such as Monosaccharides of the aldose and ketose type, which are also used from hydrogenation derived polyhydroxy compounds, pentaerythritol, trimethylolpropane, alkylglucosides, 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 be made up, for example, in the form of powders, flakes or pellets and can easily be processed into stable dispersions in water, in particular also in cold water. All you need to do is mix with water and then stir gently. The dispersions obtained are extremely stable and do not tend to separate. They can be used in the textile sector in a variety of ways to treat fibers, yarns or fabrics using the exhaust, immersion centrifugal, padding or spraying methods.

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

When the fatty acid aminoamides produced according to the invention are used in detergents, they bring about an improved cleaning action and / or an improvement in the laundry washed therewith. Finally, the fatty acid aminoamides produced according to the invention can also be used as constituents of aftertreatment agents for washed textiles, as a result of which the textiles become soft and antistatic. The aftertreatment of the washed textiles can usually be carried out in the last rinsing bath but also during drying in an automatic tumble dryer, either by spraying the laundry with a dispersion of the detergent during 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 and for washing textiles and for aftertreatment of washed laundry. Examples

1452.5 g (1.7 mol) of hydrogenated beef tallow and 176.8 g (1.7 mol) of aminoethylethanolamine are mixed in a stirring apparatus and stirred at 120 ° C. for about two hours until the residual basic nitrogen content reaches 1.05 % had dropped. The melt was cooled to 90 ° C. and neutralized with 85.8 g of a 70% by weight glycolic acid. The resulting condensation product was mixed with different amounts of an ester, which can be obtained by reacting 0.5 mol of cetyl / oleyl alcohol with 1 mol of propylene oxide (Dehypon OCP 502, Henkel) and then reacting this propylene oxide adduct with 125.0 g of technical stearic acid ( 0.45 mol) at 80 ° C in the presence of 1.2 g of toluenesulfonic acid. The product was then flaked on a chill roll.

Checking the dispersibility

Assessment of fine particles

7.5 g of the flaky products (Examples la to lc) were poured over 92.5 g of water (30 ° C., 14 ° d) in a 125 ml wide-mouth bottle. The bottle was closed, swirled briefly and stored for 16 hours. After swiveling again, suction was taken off at 150 mbar using a suction filter which was covered with a fine-mesh, black-colored polyamide fabric. After the fabric had dried, the fine particle size of the residue was assessed visually on a scale from 1 (very finely dispersed) to 6 (coarsely dispersed, many large lumps).

For comparison, the values were measured for a fatty acid aminoamide without the addition of a dispersion accelerator of the formula (II) (test VI), and another non-inventive fatty acid aminoamide, in which the non-esterified dehypon OCP 502 was used instead of the compound of the formula (II) (test V2) . The amide was always 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 are significantly superior to those without a dispersion accelerator in terms of their dispersibility. But also the addition of propoxylated fatty alcohols does not lead to the excellent results that are achieved when using the fatty acid aminoamides produced according to the invention.

Claims

claims 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) R ² H ₂ N - [(CH ₂ ) _n N] _ra -R '(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 stands for 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, O R ³ O- (C ₂ H ₄ O) _p - (C ₃ H ₆ O) _q -CR ⁴ (II) 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 of saturated fatty acids having 12 to 18 carbon atoms are used. 3. The method according to any one of claims 1 or 2, characterized in that polyamines of the general formula (I) are used in which R '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 the formula (I) are condensed in a molar ratio of 0.5: 2.0 to 2.0: 1. 5. Process according to claims 1 to 4, characterized in that the unreacted amino groups are neutralized to 20 to 80 mol%. 6. Process 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 wt .-%, based on the condensation product. 7. The method according to any one of claims 1 to 6, characterized in that such compounds of formula (II) are used in which p is 0 and q is a number between 1 and 5. 8. Use of fatty acid aminoamides according to claim 1 as a textile treatment agent.