CS263844B1 - Aminoxide - Google Patents

Abstract

The solution relates to amine oxides of general interest of formula I wherein R is alkyl polymeric carboxylic acids having 20 up to 60 carbon atoms R1 is an alkyl radical having 1 to 3 carbon atoms; m - natural numbers 2 to 3 a n - natural number 1 to 3, prepared from tertiary amidoamine and hydrogen peroxide. Tertiary amidoamine is prepared by reaction polymeric carboxylic acids with diamine. The amine oxides prepared are suitable for use recipe for fabric softeners and conditional agents.

Description

The invention relates to amine oxides useful as surfactants.

Aminooxides form hydroxylamine ions in an acidic environment, thus acting as weakly cationic surfactants. Comparing the antistatic activity of amine oxides with cationic surfactants of the classical type (dimethyldistearylammonium chloride), practically comparable results were found.

The use of amine oxides in fabric softener formulations is also suitable from an ecological point of view, since amine oxides are among the surfactants readily biodegradable. Their disadvantage is their considerable foaming, even in the case of types prepared from longer chain carboxylic acids. Also, the softening effect is weaker compared to conventional cationic surfactants.

The introduction of more alkyls has been tested with imidazoline oxides. The foaming of these substances was lower, but the synthesis of imidazolines requires equipment for working at high temperatures (200-250 ° C).

The above disadvantages do not have the amine oxide of formula I.

KR

I * _

CONH _(CH2) -N-Ol

where

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

R ¹ - (C 1 -C 3) alkyl, m - natural number 2 to 3, n - natural number 1 to 3, from a tertiary amidoamine of formula (II),

RCONH (CH ^ N no.

where

R, R ^1, m and n are as defined above, characterized by reacting 1 mole of amido amine of the general 'formula II with 1 to 1.2 mol of hydrogen peroxide at 40 to 80 ° C.

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

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

Example 1

A 800 L stainless steel reactor was charged with 564 kg of dimeric oleic acid and 214 kg of Ν, Ν-dimethyl-propylenediamine was added with stirring at 50 ° C. The mixture was stirred at 150 ° C for 6 hours. After the acid number dropped below 10, the reaction mixture was determined by titration of 3.76% N (as tertiary amine) and trace amount of primary amine, corresponding to reacting the components to the tertiary amidoamine of formula II (calculated 3.83% N - as tertiary amine) The reaction mixture was transferred to a 3,500 liter stainless steel reactor, 1570 kg of water was added, and 250 kg of 30% hydrogen peroxide was added with stirring at 50 ° C. The mixture was stirred at 50 ° C for 3 hours to obtain 2,500 kg. The amine-oxide content was determined by determining the total alkalinity and the alkalinity after blocking the tertiary amine (according to Metcalfe LD: Anal. Chem. 34, 1849 (1962)). The foaming and surface resistance of the treated fabrics are shown in Tables 1 and 2.

Example 2

According to the procedure of Example 1, 687 kg of a mixture of dimeric and trimeric oleic acid (23% dimer, 77% trimmer) and 284 kg of Ν, Ν-dimethylpropylenediamine at 160 ° C were reacted for 6 hours. After the amidation (primary trace amine content) is completed, 870 kg of water and 300 kg of propylene glycol are added to the amidoamine formed and 290 kg of 30% hydrogen peroxide are oxidized at 60 ° C. 2,400 kg of amidoxide having a concentration of 40% by weight (39.9% amine oxide calculated, calculated 41.3%) are obtained, which is suitable for the preparation of conditioners and fabric softeners.

More details are in Tab. 1 and 2.

In Table 1, the foaming of the prepared amine oxides of Examples 1 and 2 is compared with a cationic surfactant (dimethyldlstearylammonium chloride - D MDSAC) and an amine oxide prepared from N-acyl, Ν, Ν-dimethylpropylenediamine), where acyl is a rapeseed oil carboxylic acid residue).

Table 1

Foaming 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 brown 1 min 10 min. c. foaming ti tio the amine oxide of Example 1 80 30 15 Dec 66 0.4 1.9 the amine oxide of Example 2 60 45 35 49 0.8 5.9 cationakt. surfactant DSDMAC 25 15 Dec 15 Dec 16.8 1,8 3.0 rapeseed amine oxide. oils 115 80 80 76 2.1 3.5 In Table 2 indicated comparison poví- V Table 2 indicated comparison

The fabric resistance of fabrics treated in the fabric resistance of fabrics treated with the flux of the amine oxides of Examples 1 and 2. Amine oxides of Examples 1 and 2.

The surface resistance is measured on a teraohm meter.

Table 2

Surface resistance of treated fabrics (Ohm)

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

PES PAD

the amine oxide of Example 1 4.1.10 ⁹ 1,3.10 ^w the amine oxide of 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 3,4.1O ⁹ 2,4.10 ¹⁹ komerč. fabric softener. prostř. 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 present invention are comparable to commercial fabric softeners.

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.