CS240390B1 - N- [2- (dodecanoylamino) ethyl] alkylmethylammonium bromides and their preparation - Google Patents

Abstract

The invention relates to N-[2-(dodecanoylamino)-ethyl] alkyldimethylammonium bromides of the general formula O CHs II: I C11H2S—C—NH—CHz—CH2—N+—R Br~ CH3 where R represents a linear alkyl chain with a number of carbon atoms of 2 to 11, 13, 14 and a method of preparing these compounds, which consists in the reaction of the corresponding 1-bromoalkane with 2-dimethylaminoethylamide of dodecanoic acid in a methyl cyanide environment at the boiling point of the solvent. The final compounds have significant surface-active properties and antimicrobial effect on both gram-positive and gram-negative bacteria as well as yeasts, and therefore the most effective of them are usable as disinfectants with a detergency effect in cosmetics, farms, textile industry, etc., wherever it is possible to use them as surfactants or antimicrobial substances, respectively. in a combination of both of these properties.

Description

240390

The present invention relates to N- (2- (dodacanoylamino) ethyl) alkyldimethylammonium bromides of formula (O) CH3 C11H23-C-NH-CH2-CH2-N + -R Br-CH3 wherein R is a linear alkyl chain having from 2 to 11, 13, 14 and for the preparation of these compounds.

It is known that some derivatives of long-chain aliphatic carboxylic acids, in particular hydroxyalkylamides, have excellent surface-active properties, low toxicity, are little irritating, and therefore can be used in cosmetics, for example. priémysle. Most useful are the derivatives of do-decanoic acid [lauric], respectively. derivatives prepared from C10 fraction - C12 coconut oil. In the historical state, the compounds of this type derived from undecanoic, undecenoic and tetradecanoic acids are known. In addition to the above-mentioned hydroxyalkylamides, the dialkylaminoalkylamides of the fatty acids, especially 3- (dimethylaminopropyl) dodecanoic acid amide, and some derivatives thereof, such as epoxy resin additives, biocidal compositions such as antistatic agents, disinfectants and antiparasites, textile buffers, have also been used. emulsifiers.

Less known and used are their ammonium salts (mainly in the form of betaines or hydrochlorides), for example as flotation agents, anti-corrosion additives, photographic preparations, migration agents for coloring baths, food preservatives, antiparasites.

In addition to the dodecyl derivative, the compounds of the above structure which are the subject of the present invention in which naammonium nitrogen bound alkyl chains of 2 to 14 carbon atoms (together with the two-methyl groups) are not described in the literature. They have not yet been known to have effects on micro-organisms. Among the most effective, the anti-microbial activity is significantly higher compared to the commonly used organic disinfectants.

The process for preparing the compounds according to the invention is carried out in the reaction of 2-dimethylaminoethylamide dodecanoic acid with the corresponding 1-bromoalkane in methyl cyanide at the temperature of the solvent. Compared to the novel methods for preparing organic ammonium salts (e.g. using water, methanol, ethanol as reaction medium), the present invention has the advantage of avoiding by-products (e.g., hydrolysis or re-esterification reactions) and to form final compounds in high yields. The examples illustrate a method for preparing selected compounds of the invention. In addition to yield, melting point, Rp-value (determined by silica gel in the acetone: 1 M HCl 1: 1 system, detection by Dragendorf reagent in the mune modification), the IC-spectral characteristic (measured in nujol sus-buffer, in cm 4) is their critical concentration of Ck (in mol. dm-3), maximum reduction in surface tension in Ck (yck, in nM. m-1), as well as antimicrobial activity against Staphylococcus aureus, Escherichia coli and Candida albicans expressed as minimal inhibitory concentration. MICv μ§. cm-3. EXAMPLE 1 0.1 ml of 2-dimethylaminoethylamide of dodecanoic acid is dissolved in 30 cm @ 3 of methyl cyanide, 0.11 mol of 1-bromoethane is added and heated at the boiling point of the solvent for 4 hours. After evaporation of the methyl cyanide, the product crystallizes to a constant temperature of melting. There was thus obtained N - [2- (dodecanoylamino) ethyl] ethyldimethylammonium bromide in 99% yield; mp 80-82 ° C;

Rp = 0.56; IR: vNH trans 3 420, cis 3 200, 3 177, yc = o (Amide I) 1050, VCN + OcNH (Amid II) 1 539, i> cn 1152, V (cn) + ^ cc Ί- <5 ( NH) p.p. (Amide III) 1299, p cm 720;

Ck = 1.0.10-2, yck = 38.7; MIC: 40, 600, 200

The working procedure is the same as in Example 1 except that 1-bromoctane was used instead of 1-bromoethane. N- [2- (dodecanoylamino) ethyl] octyldimethylammonium bromide was obtained in 84% yield. ; mp 84-86 ° C;

Rf = 0.67; ID No .: NH trans 3 430, 3 376, 3 324, cis 3 228, 3 192,

Amide I 1,649,1674;

Amide II 1542, v CN 1173, Amide III 286, p CH2 721;

Ck = 1.1.10-3, yck = 30.7; MIC: 1, 10, 1

The working procedure is the same as in Example 1 except that 1-bromotetradecane was used in the reaction. N- [2- (dodecanoylamino) ethyl] tetradecyldimethylammonium nimbromide was obtained in 92% yield; mp 94-96 ° C;

Rf = 0.51; IR: vNH trans 3 404, 3 324, cis 3 228, 3 192,

Claims (2)

SUBJECT 1. N- [2- (dodecanoylamino) ethyl] alkyldimethylammonium bromides of the general formula O CH3 II -I. C11H23-C-NH-CH2-CH2-N ⁺ -R Br- CH3 wherein R is a linear alkyl chain having 2 to 11, 13, 14 carbon atoms. 2. A process for the preparation of compounds of the general formula as in 1, characterized in that: C _k = 3.9.10 ^-5 ; yc _k = 25.3; MIC: 1400,> 1000, 700. OF THE INVENTION reacts dodecanoic acid 2-dimethylaminoethylamide of formula ABOUT II C11H23-C-NH-CH2-CH2-N (CH3) 2 with 1-bromoalkane of general formula R = Br wherein R is as defined in point 1, in methyl cyanide at the boiling point of the solvent.