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

N,n'-bis(alkyldimethyl)-2-dodecanoyloxy-1,3-propandiamoniumdibromides and method of their preparation Download PDF

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CS245094B1
CS245094B1 CS852768A CS276885A CS245094B1 CS 245094 B1 CS245094 B1 CS 245094B1 CS 852768 A CS852768 A CS 852768A CS 276885 A CS276885 A CS 276885A CS 245094 B1 CS245094 B1 CS 245094B1
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bis
preparation
dodecanoyloxy
alkyldimethyl
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Ferdinand Devinsky
Ivan Lacko
Lubomira Masarova
Monika Rafajdusova
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Ferdinand Devinsky
Ivan Lacko
Lubomira Masarova
Monika Rafajdusova
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Vynález sa týká N,N‘-bis(alkyldimetylj-2-dodekonayloxy-l,3-propyndiamóniumdibromidov všeobecného vzorcaThe invention relates to N, N‘-bis (alkyldimethyl) -2-dodeconayloxy-1,3-propyndiammonium dibromides of the general formula

CilH23COOGH['CHaN©(CH3)2R]2 2 Br© kde R znamená lineárny alkylový reťazec s počtem atómov uhlíka 1 až 16 a sposobu přípravy týchto zlúčenín.Wherein R is a linear alkyl chain having a carbon number of 1 to 16 and a process for preparing these compounds.

Boj proti nežiadúcim mikroorganizmem je neustále pretrvávajúcim aktuálnym problémom nielen zdravotnictva, ale zasahujúcim do rozličných oblastí priemyslu (farmaceutický, kozmetika, potravinářsky, ροϊηοhospodárstvo) a významnou mierou ovplyvňujúci aj hospodárstvo. Preto sa hfadajú nové zlúčeniny, ktorých antimikróbna aktivita by bola vysoká, ale vedfajšie nežiadúce biologické účinky by boli v maximálnej miere potlačené.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.

Je známe, že organické amóniové soli obahujúce vo svojej molekule najmenej jeden alkylový reťazec s počtom atómov uhlíka 8 a viac vykazujú výrazný antimikróbný účinek, á preto našli široké použitie v dezinfekčnej praxi. Ukázalo sa výhodné spojenie ich detergenčných vlastností s vysokou biologickou aktivitou, a preto je možné použit tieto zlúčeniny ako dezinfekčně tenzidy.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.

Nevýhodou klasických používaných dezinfekčných zlúčenín z radu organických amóniových solí je ich poměrně vysoká odolnost voči vonkajším vplyvom, pretože okrem dlhého uhlovodíkového reťazca neobsahuji! vo vačšine prípadov biodegradabilné skupiny.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.

Túto nevýhodu odstraňujú zlúčeniny, ktoré vo svojej molekule obsahujú skupiny blízké živým systémom (například amidovú, esterová, hydroxylovú a pod. J. Do takéjto skupiny patria aj zlúčeniny, ktoré sú predmetom vynálezu. Ako jednu zo štrukturálnych súčastí obsahujú esterovú skupinu, ktorá poměrně 1'ahko podlieha hydrolytickým reakciám, predovšetkým vtedy, ak sú tieto katalyzované enzýmami. Výsledné produkty primárného rozkladu — kyselina dodekánová a příslušné substituovaný izopropylalkohol výrazné menej zaťažujú životné prostredie ako povodná amóniová sol'.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.

Sposob přípravy zlúčenín, ktoré sú predmetom vynálezu, je založený na SN2 reakcii 1-brómalkánu s l,3-bis(dimetylamino)-2-propylesterom kyseliny dodekánovej v prostředí metylkyanidu pri teplote 20 °C až 80° Celcia. Tento sposob přípravy má tu výhodu v porovnaní s inými metodami přípravy (například za použitia vody, alkoholov ako rozpúšťadiel), že sa zabráni vzniku vedlejších produktov, například preesterifikačnými reakciami. Ďalšou výhodou postupu podlá vynálezu je, že po ochladení reakčnej zmesi sa ihned' získajú produkty vysokej čistoty v poměrně dobrých výťažkoch. Takto připravené zlúčeniny sú doetatočne čisté pre ďalšie použitie, dajú sa však čistit ďalšou kryštalizáciou.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.

« *·· tfPříklady ilustruji! ale neobmedzuijú metodu přípravy zlúčenín podlá vynálezu. Okrem výtažku, teploty topenia, Rf-hodnót (silikagél, sústava aceton : 1 M HC1 1 : 1, detekcia Dragendorfovým člnidlom v Munierovej modifikácii), IČ-spektrálnych charakteristik (namerané v nujolovej suspenzii, v cm'1), je uvedená aj ich kritická koncentrácia tvorby miciel Ck (v mol. dm-3), maximálně zníženie povrchového napátia pri Ck (yck, v mN.nr1) ako aj doteraz neznáma antimikróbna aktivita voči Staphylococcus aureus, Escherichia coli a Candida albicans vyjádřená ako minimálna inhibičná koncentrácia MIC v ,ug . cm-3.«* ·· 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 .

Příklad 1Example 1

V 30 cm3 metylkyanidu sa rozpustí 0,05 molu l,3-bis(dimetylamípo)-2-propylesteru kyseliny dodekánovej, přidá sa 0,11 molu 1-brómetánu a nechá sa reagovat pri teplote 20 QC 24 hodin. Potom sa 4 hodiny zahrieva pri teplote varu rozpúšťadla. Po ochladení sa vykrystalizovaný produkt odfiltruje, premyje suchým éterom a krystalizuje do konstantně j teploty topenia (aj bez ďalšej kryštalizácie je produkt dostatečné čistý pre ďalšie použitie). Získá sa N,N‘-bis(etyldimetyl)-2-dodekonayloxy-l,3-propándiamóniumdibromid vo výtažku 66 %; t. t. 222 až 223 °C;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;

Rř = 0,54;R f = 0.54;

IČ: vc=0 1741,IR: v c = 0 1741,

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

GH2GH2

Ck = l,4.10-2;C k = 1.4.10 -2 ;

= 46,0;= 46.0;

MIC: 200, 2 000, 400.MIC: 200, 2000, 400.

Příklad 2Example 2

Pracovný postup je ten istý ako v príkladede 1 s týni rozdielom, že namísto 1-brómetánu sa do reakcie použil 1-brómoktán a reakcia prebiehala ihned' od zaČiatku pri teplote varu rozpúšťadla počas 36 hodin. Vznikol N,N‘-bis (oktyldimetyl )-2-dodekonoyloxy-l,3-propándiamóniumbibromid vo výtažku 66 %; t. t. 191 až 192 °C;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;

Rf = 0,69;R f = 0.69;

IČ: vc„o 1743,IR: v c "of 1743,

Vc-o-c 1146, p 720;[Nu] C-O-C 1146, p 720;

CH2 •Ck - 5,3. 104;CH2 • C k = 5.3. 104;

rc · 34,0; γ ©. rc · 34.0; γ ©.

k ; 'k ; '

MIC: 2, 20, 2.MIC: 2, 20, 2.

Příklad 3Example 3

Pracovný postup je ten istý ako v příklade 2 s tým rozdielom, že namiesto 1-brómoktánu sa do reakcie použil 1-brómhexadekán.The procedure is the same as in Example 2 except that 1-bromohexadecane was used in the reaction instead of 1-bromooctane.

245034245034

Vznikol N,N‘-bis(hexadecyldimetyl)-2-dodekanoyloxy-l,3-propándiamóniumdibromid vo výtažku 82 lO/o; t. t. 179 až 181 °C;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; Rf = 0.13;

IC: vc=o 1731,IR: C = O 1731,

Claims (2)

1. N,N‘-bis(alkyldimetyl)-2-dodekanoyloxy-l,3-propándiamóniumdibromidy všeobecného vzorca1. N, N‘-Bis (alkyldimethyl) -2-dodecanoyloxy-1,3-propanediammonium dibromides of the formula CilHžóCOOCHfCttzN© (CH3)2R ] 2 2 Br© kde R znamená lineárny alkylový reťazec s počtom atómov uhlíka 1 až 16.Wherein R represents a linear alkyl chain having a carbon number of 1 to 16. 2. Spósob přípravy zlúčenín všeobecného vzorca ako v bode 1, vyznačený tým, že sa vc-o-c 1151, p 718;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; CHzCH Ck = l,2.10-5;C a = l, 2.10- 5; Zc - 52,2;Zc - 52.2; kto MIC: 800, —, 6 000.MIC: 800, -, 6,000. VYNÁLEZU nechá zreagovať l,3-bis(dimetylamíno)-2 -propylester kyseliny dodekánovej vzorcaOF THE INVENTION is reacted dodecanoic acid 1,3-bis (dimethylamino) -2-propyl ester of the formula CuH23COOCH [CH2N (CH3) 2 ] 2 s l-brómalkánorti všeobecného' vzorcaCuH 23 COOCH [CH 2 N (CH 3) 2] 2 with a 1-bromoalkanorti of formula R—Br kde R má ten istý význam ako v bode 1 pri teplote 20 CC až 80 °C.R = Br wherein R is as defined in point 1 at 20 ° C to 80 ° C.
CS852768A 1985-04-15 1985-04-15 N,n'-bis(alkyldimethyl)-2-dodecanoyloxy-1,3-propandiamoniumdibromides and method of their preparation CS245094B1 (en)

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