CS240389B1 - N-/2-/dodecanoylmethylamino/ethyl/alkyldimethylamonium-bromides and method of their preparation - Google Patents

Abstract

The invention relates to N- [2- (dodecanoylmethylamine) ethyl] alkyldimethylammonium bromides formula O CH3 CuHSs-C-N-CH2-CH2-N + -R BrCH3 CH3 wherein R is a linear alkyl chain with a carbon number of 2 to 14 and a method the preparation of these compounds the reaction of the corresponding 1-bromoalkane with N, N‘, N‘- dodecanoic acid trimethylaminoethylamide in the medium of cyanide at temperature boiling solvent. Finally, the compounds have a pronounced surface finish active properties and antimicrobial effect so on gram-positive, gram-negative bacteria as well as yeast. The most effective of them are useful as detergent disinfectants effects in cosmetics, pharmacy, etc. wherever their properties can be exploited surfactants or antimicrobial agents substances, respectively. in combination of these two Properties.

Description

and how to prepare them

The invention relates to N- [2- (dodecanoylmethylamino) ethyl] alkyldimethylammonium bromides of the general formula

O CH3

CuHSs-C-N-CH2-CH2-N R + Br ^-

CH 3 CH 3 wherein R represents a linear alkyl chain having 2 to 14 carbon atoms and a process for preparing these compounds comprising reacting the corresponding 1-bromoalkane with N, N ‘, N‘-trimethylaminoethylethylamide dodecanoic acid in methyl cyanide at the boiling point of the solvent.

Finally, the compounds have significant surface-active properties and an antimicrobial effect on both Gram-positive, Gram-negative bacteria and yeast. The most effective of these are useful as disinfectants with detergent effect in cosmetics, pharmacy, etc. wherever it is possible to utilize their properties of surfactants or antimicrobial active substances, respectively. in combination of both.

The invention relates to N- [2- (dodecanoylmethylamino) ethyl] alkyldimethylammonium bromides of the general formula

O CH3

II I

C11H23- c — N — CH2 — CH2 — N ⁺ —R Br '

CH 3 CH 3 wherein R represents a linear alkyl chain having a carbon number of 2 to 14 and a process for the preparation of these compounds.

Long-chain aliphatic carboxylic acids and their derivatives are groups of compounds which, in addition to their great biological significance, are of industrial use. Due to their excellent surface-active properties and negligible undesirable side effects, they are advantageously used, in particular hydroxyalkylamides having a secondary amide group, in cosmetics, pharmacy and in various industrial sectors. Of this type of compound, dodecanoic acid derivatives are most commonly used, but compounds with shorter or longer alkyl chains are also known. The hydrocarbon chain may be saturated or unsaturated or substituted.

Less known and used are the ammonium salts of omega-aminoalkylamides of carboxylic acids with variously substituted omega-amino compounds, which are used in particular in the form of beta-amines or ammonium chlorides. Tertiary amide derivatives (except bis [hydroxyethyl] compounds) are used only to a very limited extent.

The compounds of the present invention which contain a tertiary amide group in their molecule and an alkyl chain of 2 to 14 carbon atoms attached to the ammonium nitrogen have not been known. They have so far unknown effects on microorganisms, the most effective of which have a higher effect than the commonly used disinfectants of the type of organic ammonium salts - Ajatin and Septonex. Also unknown surfactant properties were found for all these compounds. Compared to compounds of a similar type containing a secondary amide group in their molecule, these compounds are also more advantageous in that they, due to the presence of a tertiary amide group, exclude the possibility of the formation of N-nitrosamines (found in secondary amides), carcinogenic effect.

A process for the preparation of the compounds of the invention consists of reacting dodecanoic acid N, N ', N'-trimethylaminoethylamide with the appropriate 1-bromoalkane in methyl cyanide at the boiling point of the solvent. The process according to the invention has the advantage over other methods of preparing organic ammonium salts (for example using water, methanol, ethanol as reaction medium) that by-products (resulting, for example, from hydrolytic or pre-esterification reactions) are avoided and f is formed _; in high yields and high purity.

The Examples illustrate a method for preparing selected compounds of the invention. In addition to the yield, melting point, _Rf -values (determined on silica gel with acetone: 1 M HC1 1:

: 1, detection by Dragendorf reagent in Munier modification), IC-spectral characteristics (measured in nujol suspension, in cm ^-1 ), their critical concentration of micelle formation (in mol dm ' ³ ), maximum reduction of surface tension at Ck (yck, in mN.m ^-1 ), as well as antimicrobial activity against Staphylococcus aureus, Escherichia coli and Candida albicans expressed as the minimum inhibitory concentration of MIC at µg. cm ' ³ .

Example 1

Dissolve 0.1 mole of N, N ', N'-trimethylaminoethylamide dodecanoic acid in 30 cm ^{3 of} methyl cyanide, add 0.11 mole of 1-bromoethane and heat at the boiling point of the solvent. After evaporation, the solvent crystallizes to a constant melting point. N- [2- (dodecanoylmethylamino) ethyl] ethyldimethylammonium bromide is obtained in a yield of 99%;

t. t. 74-75 ° C;

_Rf = 0.52;

IR: in Nci-h 2,725, υ c = o 1,640,

Δ (CH 2 N, Jocking 1187, 1 019, p ch 2 716;

C _k = 9.1 x 10 ³ ;

From the ^c = 43.2;

MIC: 50, 200, 80.

Example 1 a d 2

The procedure is the same as in Example 1, except that 1-bromooctane was used in the reaction instead of 1-bromoethane. N- [2- (dodecanoylmethylamino) ethyl] octyldimethylammonium bromide was obtained in 85% yield;

t. t. Mp 76-78 ° C;

_RF = 0.70;

IR: In NCH3 2 728, in _c = o 1 640,

240389 5 δ (CH3N.CJrocking 1 199, 1 019, ρ ch2 723;

C _a = l, 3.10- ^3;

/ c = _about 33.9;

MIC: 1, 30, 6.

EXAMPLE 1 a d 3

The procedure is identical to that described in Example 1 except that 1-bromo-tetradecane was used as the alkylating agent in place of 1-bromoethane in the reaction. N- [2- (dodecanoylmethylamino) ethyl] tetradecyldimethylammonium bromide was obtained in a yield of 92%;

Claims (2)

SUBJECT 1. N- [dodecanoylmethylamino) ethyl] alkyldimethylammonium bromides of the general formula O CH3 II I C11H23 — C — N — CH2 — CH2 — N ⁺ —R Br- CH 3 CH 3 wherein R represents an alkyl chain having 2 to 14 carbon atoms. 2. A process for the preparation of compounds of the general formula as in 1, which comprises reacting dodecanoic acid N, N @ -, N @ - trimethylaminoethylamide of the formula: t. t. 88-90 ° C; - _Rf = 0.63; IR: NCH3 2,727, c-o 1,634, S (CH 3 N, C) rocking 1193, 1016, p ch2 721; C _k = 1.3. ⁴ '⁴; _{rc k} = 27.5; MIC: 500, > 1,000, 80. INVENTION ABOUT CnHa3-C-N-CH2-CH-N (CH 3) 2 CH3 with 1-bromoalkane of the general formula R = Br wherein R is as defined in point 1, in methyl cyanide at the solvent temperature.