CS252548B1 - N, N‘-bis (alkyldimethyl) -2-dodecyloxy-1,3-propanediammonium dibromides and their preparation - Google Patents

Abstract

The solution concerns N,N'-bis(alkyldimethyl)-2-dodecyloxy-1,3-propanediammonium dibromides of the general formula where R denotes a linear or branched alkyl chain with the number of carbon atoms from 1 to 14 and the method of preparation of these compounds, which consists in the reaction of the respective bromoalkane with N,N'-bisdimethyl-2-dodecyloxy-1,3-propanediamine in an environment of methyl cyanide at the boiling temperature of the solvent for 12 to 16 hours. Finally, the compounds have significant surface-active properties and a broad-spectrum antimicrobial effect, including gram-positive and gram-negative bacteria, yeasts and algae. They can be used as disinfectants with a simultaneous cleaning effect, as preservatives, detergents, auxiliary substances, etc.

Description

The present invention relates to N, N‘-bis (alkyldimethyl) -2-dodeicyloxy-1,3-propanediammonium dibroimido, wherein R is a linear or branched alkyl chain having from 1 to 14 carbon atoms and a process for the preparation of these compounds.

Bisammonium salts form the sixth generation of antimicrobically active organic ammonium compounds and represent a relatively new class of substances which, however, are already known to exhibit excellent antimicrobial effects in addition to their surfactant properties (if the molecule contains at least one long alkyl chain). Their antimicrobial effect, compared to classical monoammonium salts, is potentiated against relatively resistant gram-negative bacteria, while also showing very high activity against gram-positive bacteria but also yeast and algae. In addition to the biocidal effect, they also have a detergent effect due to their ability to significantly reduce surface tension at the liquid-gas interface.

Some simple types of bisammonium salts have been described in the chemical literature, however, the compounds of the present invention are novel substances not previously described in the chemical literature, which have hitherto unknown biological effects and physical properties.

The preparation of these compounds consists in reacting N, N‘-bisdimethyl-2-dodecyloxy-1,3-propanediamine with a bromoalkane mechanism of a nucleophile bimolecular substitution mechanism in methyl cyanide at the boiling point of the solvent for 12-16 hours. An advantage of the method according to the invention over the known methods is that products in high yield are produced in some cases, the yields are quantitative and very pure. Due to the reduced reactivity of the reactants resulting from their structure, it is essential to maintain the reaction time to achieve high yields.

The examples illustrate but do not limit the general! a method of preparing the compounds of the invention and characterizing their properties and effects. In addition to yields, melting point, IR spectral characteristics (nujol, vv cm ¹ ), R (values [acetone-HCl (c _HCl -1 mol. Dm ^-3 ), silica gel valid Silufol, detection by Dragendorf reagent in Munier modification] are reported. also aggregation center of micelle formation (C _k in mol.dm ^-3 ), center of micelle formation (Ck in mol dm ^-3 ), surface-active properties characterized by maximal reduction of surface tension at Ck (/ ck in m Nm ^-1 ) as also antimicrobial activity characterized by a minimal inhibitory concentration (MIC v, µg. cm ^-3 ) against Staphylococcus aureus, Escherichia coli and Candida albicans. S. aureus 20 times, E coli 8 times and C. albicans 4 times.

Example 1

0.1 mole of N, N'-bisdimethyl-2-dodecyloxy-1,3-propanediamine and 0.21 mole of bromomethane are added to 30 cm @ ^{3 of} methyl cyanide. The reaction mixture was heated to reflux for 12 hours. After cooling and distilling off the solvent, the product is recrystallized from dry acetone. The yield of N, N'-bis (ethyldimethyl) -2-dodecyloxy-1,3-propanediammonium dibromide is 91%; mp 156-158 ° C; Rf = 0.48; Vas (coc) 1093; pcH2 717; Ck = 1 , 68.10 ^-2 ; yck = 45.6; MIC: 20, 500, 300. Example 2

The procedure was the same as in Example 1 except that bromohexane was used instead of bromomethane and the reaction time was 14 hours. The yield of N, N'-bis (hexyldimethyl) -2-dodecyloxy-1,3-propanediammonium dibromide is 75%; tt 208-210 degrees Celsius; R ₍₌ 0.55, _and the _(c OC) 1098, p 717 _{CH 2,} C _k == 2.06. 10 ^-3, y = _C of 36.2, MIC: 1, 40 4.

Example 3

The procedure was the same as in Example 1 except that bromotetradecane was used instead of bromomethane and the reaction time was 16 hours. The yield of N, N'-bis (tetradecyldimethyl) -2-dodecyloxy-1,3-propanediammonium dibromide is quantitative; mp 207-208 ° C; R f = 0.31; at _{as (C} -oc) 1092, p ch 2717 ; C _k - 1.54.10 ^-5 ; _{/ ck} = 33.4; MIC: 8,000.- 1,000.

Claims (2)

OBJECT OF THE INVENTION 1. N, N alky-bis (alkyldimethyl) -2-dodecyloxy-1,3-propanediammonium dibromides of general formula ~ O ~ Cci wherein R is a linear or branched chain alkyl group having from 1 to 14 carbon atoms. 2. A process for the preparation of general formula compounds as in 1, characterized in that N, N'-bisdimethyl-2-dodecyloxy-1,3-propanediamine of formula C1ZH25-O-CH [CH2N (CH3) 2] 2 with bromoalkanes is reacted. of formula R-Br wherein R is the same as in point 1 in a cyanide at a boiling point of the solvent for 12 to 16 hours.