CS245094B1 - N,n'-bis(alkyldimethyl)-2-dodecanoyloxy-1,3-propandiamoniumdibromides and method of their preparation - Google Patents

Description

The invention relates to N, N‘-bis (alkyldimethyl) -2-dodeconayloxy-1,3-propyndiammonium dibromides of the general formula

Wherein R is a linear alkyl chain having a carbon number of 1 to 16 and a process for preparing these compounds.

The fight against unwanted micro-organisms is a persistent topical problem not only of health care but also affecting various sectors of the industry (pharmaceutical, cosmetics, food, food and beverage) and has a significant impact on the economy. Therefore, new compounds are sought whose antimicrobial activity would be high, but the adverse side effects of biological effects would be suppressed to the maximum extent.

It is known that organic ammonium salts containing in their molecule at least one alkyl chain having a carbon number of 8 or more exhibit a significant antimicrobial effect and have therefore found widespread use in disinfection practice. It has been shown to advantageously combine their detergent properties with high biological activity, and therefore, these compounds can be used as disinfectant surfactants.

The disadvantage of the traditional disinfectants used in the organic ammonium salt series is their relatively high resistance to external influences, as they do not contain in addition to the long hydrocarbon chain! in most cases, a biodegradable group.

This disadvantage is overcome by compounds which contain in their molecule groups closely related to living systems (for example, amide, ester, hydroxyl, etc.). This group also includes the compounds of the present invention. The resulting primary decomposition products - dodecanoic acid and the corresponding substituted isopropanol - have a significantly lower environmental impact than the flood ammonium salt.

The process for preparing the compounds of the invention is based on the S _N 2 reaction of 1-bromoalkane with 1,3-bis (dimethylamino) -2-propyl dodecanoic acid ester in methyl cyanide at 20 ° C to 80 ° Celsius. This method of preparation has the advantage over other methods of preparation (for example using water, alcohols as solvents) that the formation of by-products is avoided, for example by pre-esterification reactions. A further advantage of the process according to the invention is that after cooling the reaction mixture, products of high purity are obtained immediately in relatively good yields. The compounds thus prepared are instantly pure for further use, but can be purified by further crystallization.

«* ·· tfExample I illustrate! but do not limit the method of preparation of the compounds of the invention. In addition to the yield, melting point, _Rf -hodnót (silica gel, acetone system: 1 M HC1 1: 1, detection of the agent it Dragendorfovým Munierovej modification), IR-spectral characteristics (measured in nujol mull, in ^cm-1), the said their critical concentration of micelle formation (in mol dm ^-3 ), maximum reduction of surface tension at Ck (yc _k , in mN.nr ¹ ) as well as hitherto unknown antimicrobial activity against Staphylococcus aureus, Escherichia coli and Candida albicans expressed as minimal inhibitory MIC concentration in µg. cm ^-3 .

Example 1

The 30 cm ³ methyl cyanide is dissolved 0.05 mole l, 3-bis (dimetylamípo) propyl-2-dodecanoic acid, was added 0.11 mol of 1-bromoethane and treated at 20 ^Q C for 24 hours. It is then heated at the boiling point of the solvent for 4 hours. After cooling, the crystallized product is filtered off, washed with dry ether and crystallized to a constant melting point (even without further crystallization the product is pure enough for further use). N, N'-bis (ethyldimethyl) -2-dodeconayloxy-1,3-propanediammonium dibromide is obtained in a yield of 66%; mp 222-223 ° C;

R _f = 0.54;

IR: v _{c = 0} 1741,

[Nu] C-o-c 1148, p 717;

GH2

C _k = 1.4.10 ^-2 ;

= 46.0;

MIC: 200, 2000, 400.

Example 2

The procedure was the same as in Example 1 except that 1-bromoethane was used instead of 1-bromoethane and the reaction was carried out immediately from the start at the boiling point of the solvent for 36 hours. N, N‘-bis (octyldimethyl) -2-dodeconoyloxy-1,3-propanediammonium bromide was obtained in 66% yield; t. t. Mp 191-192 ° C;

R f = 0.69;

IR: v _c "of 1743,

[Nu] C-O-C 1146, p 720;

CH2 • C _k = 5.3. 104;

_rc · 34.0; ^γ ©.

k ^; '

MIC: 2, 20, 2.

Example 3

The procedure is the same as in Example 2 except that 1-bromohexadecane was used in the reaction instead of 1-bromooctane.

245034

N, N'-bis (hexadecyldimethyl) -2-dodecanoyloxy-1,3-propanediammonium dibromide was obtained in a yield of 82 ¹⁰ / o; mp 179-181 ° C;

_Rf = 0.13;

IR: _C = O 1731,

Claims (2)

1. N, N‘-Bis (alkyldimethyl) -2-dodecanoyloxy-1,3-propanediammonium dibromides of the formula Wherein R represents a linear alkyl chain having a carbon number of 1 to 16. 2. A process for the preparation of compounds of the general formula as in 1, characterized in that in c-o-c 1151, p 718; CH C _a = l, 2.10- ^5; Zc - 52.2; to MIC: 800, -, 6,000. OF THE INVENTION is reacted dodecanoic acid 1,3-bis (dimethylamino) -2-propyl ester of the formula CuH 23 COOCH [CH 2 N (CH 3) 2] 2 with a 1-bromoalkanorti of formula R = Br wherein R is as defined in point 1 at 20 ^° C to 80 ° C.