CS263844B1 - Aminoxide - Google Patents

Abstract

The solution relates to amino oxides of the general formula I, in which R denotes an alkyl radical of a polymeric carboxylic acid with 20 to 60 carbon atoms, R1 — an alkyl radical with 1 to 3 carbon atoms, m — a natural number of 2 to 3 and n — a natural number of 1 to 3, prepared from a tertiary amidoamine and hydrogen peroxide. The tertiary amidoamine is prepared by reacting a polymeric carboxylic acid with a diamine. The prepared amino oxides are suitable for use in the formulations of fabric softeners and conditioners.

Description

The invention relates to amino oxides useful as surfactants.

Amine oxides form hydroxylamine ions in an acidic environment, thus acting as weakly cationic surfactants. When comparing the antistatic effectiveness of amine oxides with cationic surfactants of the classical type (dimethyldistearyl ammonium chloride), practically comparable results were found.

The use of amino oxides in fabric softener formulations is also suitable from an ecological point of view, as amine oxides are among the surfactants that are easily biodegradable. The disadvantage is their considerable foaming, even in the types prepared from carboxylic acids with a longer chain. The softening effect is also weaker compared to classic cationic surfactants.

The introduction of more alkyl groups was tested with imidazoline oxides. The foaming properties of these compounds were lower, but the synthesis of imidazolines requires equipment capable of operating at high temperatures (200 to 250 °C).

The amine oxide of general formula I does not have the above-mentioned disadvantages.

KR

I* _

CONH( _CH2 )-N-Ol

where

R denotes an alkyl radical of a polymeric carboxylic acid having 20 to 60 carbon atoms.

R ¹ — alkyl radical with 1 to 3 carbon atoms, m — natural number 2 to 3, n — natural number 1 to 3, from a tertiary amidoamine of general formula II,

RCONH (CH^N no.

where

R, R ¹ , and m have the above-mentioned meaning, characterized in that 1 mol of amidoamine of general formula II is reacted with 1 to 1.2 mol of hydrogen peroxide at a temperature of 40 to 80°C.

The starting amidoamine is prepared by reacting a dimeric or trimeric carboxylic acid or a mixture thereof with the corresponding diamine.

The preparation of amine oxides is shown in the following examples.

Example 1

564 kg of dimer oleic acid are charged into an 800 l stainless steel reactor and 214 kg of N,N-dimethylpropylenediamine are added with stirring at a temperature of 50° C. The mixture is stirred for 6 hours at 150° C. After the acid number dropped below 10, 3.76% N (as tertiary amine) and a trace amount of primary amine were determined by titration in the reaction mixture, which corresponds to the reaction of the components to the tertiary amidoamine of formula II (calculated content 3.83% N — as tertiary amine). The reaction mixture is transferred to a 3,500 liter stainless steel reactor, 1,570 kilograms of water are added and 250 kg of 30% hydrogen peroxide are added while stirring at 50 °C. The mixture is stirred at 50 °C for 3 hours. 2,500 kilograms of approximately 30% amine oxides are obtained, which are used for the preparation of fabric softeners. The content of amine oxides was determined by determining the total alkalinity and alkalinity after blocking the tertiary amine [according to Metcalfe L. D.: Anal. Chem. 34, 1849 (1962)]. The determined content 28.9%, calculated 30.5%. The foaming capacity and surface resistance of the treated fabrics are in Tables 1 and 2.

Example 2

According to the procedure in Example 1, 687 kilograms of a mixture of dimer and trimer oleic acid (23% dimer, 77% trimer) and 284 kg of N,N-dimethylpropylenediamine are reacted at 160 °C for 6 hours. After completion of amidation (trace content of primary amine), 870 kg of water and 300 kilograms of propylene glycol are added to the resulting amidoamine and 290 kg of 30% hydrogen peroxide are oxidized at 60 °C. 2,430 kg of amidoxide with a concentration of 40% by weight (39.9% amine oxide determined by titration, 41.3% calculated) is obtained, which is suitable for the preparation of conditioning and fabric softening agents.

More detailed information is provided in Tables 1 and 2.

Table 1 compares the foaming properties of the prepared amine oxides from Examples 1 and 2 with a cationic surfactant (dimethyl distearyl ammonium chloride — DMDSAC) and an amine oxide prepared from N-acyl, N,N-dimethylpropylenediamine), where acyl is a residue of carboxylic acids of rapeseed oil.

Table 1

Foaming ability of amine oxides according to Ross-Miles

Conditions:

distilled water temperature 20 °C concentration 100% active substance 0.4 g. I ^{1 * * * * *}

sample foam column height (mm) foam stability immediately 1 minute 10 minutes c. foaming those tho amine oxide according to example 1 80 30 15 66 0.4 1.9 amine oxide according to example 2 60 45 35 49 0.8 5.9 cationic surfactant DSDMAC 25 15 15 16.8 1.8 3.0 rapeseed oil amine oxide 115 80 80 76 2.1 3.5 In Table 2 is stated comparison tell- V table 2 is stated comparison

of the resistance of fabrics treated with the solution of amine oxides from examples 1 and 2. of the resistance of fabrics treated with the solution of amine oxides from examples 1 and 2. Surface

Surface resistance is measured on a TERALIN III teraohmmeter using a stainless steel knife probe.

Table 2

Surface resistance of treated fabrics (Ohm) Conditions:

temperature 22 °C relative humidity 65 % conc. 100% active substance 0.4 g . 1 ^_1

DOG PAD

amine oxide according to example 1 4,1.10 ⁹ 1.3.10 ^watts amine oxide according to example 2 8,6.10 ⁹ 1,6.10 ¹⁰ cationic surfactant DSDMAC 1,4.10 ⁸ 1.6.10 ^ω rapeseed oil amine oxide 3,4.10 ⁹ 2,4.10 ¹⁹ commercial fabric softener 2,8.10“’ 8.0.10 untreated fabric 1,7.10 ¹³ 8.0.10 ¹³

It is clear from the tables that the amine oxides of the invention are comparable to commercial fabric softener products.

Claims (1)

An amine oxide of formula (I) wherein: R is an alkyl radical of a C 20 -C 60 polymeric carboxylic acid, R ^{1 is an} alkyl radical having 1 to 3 carbon atoms, m is a natural number of 2 to 3, n is a natural number of 1 to 3.