Resumen
PCT No. PCT/ES96/00026 Sec. 371 Date Dec. 13, 1996 Sec. 102(e) Date Dec. 13, 1996 PCT Filed Feb. 8, 1996 PCT Pub. No. WO96/24528 PCT Pub. Date Aug. 15, 1996Surfactants having general formula (II) wherein X=8-14; n=2-8. The process for obtaining such surfactants comprises the following steps; a) producing nitroarginin; b) producing N alpha -acyl-nitroarginin c) producing N alpha N omega bis (N alpha acyl-arginin) alpha , omega diaminoalkylamide dichlorohydrate. Said surfactants are antimicrobial agents which can be applied in cosmetics, pharmacy and food industry.
Reivindicaciones
1. Cationic geminal surfactants of the type N< alpha >N< omega >bis(N< alpha >acyl-arginin) alpha , omega ,diamino alkyl dichlorohydrates as antimicrobial agents with high surface activity, characterized by the general formula: <img class="EMIRef" id="10163093-00140001" /> x = 8-14 n = 2-8 2. Procedure for the obtention of cationic surfactants with the general formula according to claim 1, characterized by the folowing stages: a) Formation of nitroarginin, using as starting aminoacid, L-arg, D-arg or DL-arg and as protector of the guanidino group of the arginin, the HClnitro group. b) Formation of N< alpha >-acyl-nitroarginin parting from the nitroarginin and fatty acid, using lineal fatty acid chlorides of 10 - 18 atoms as acilants of the nitroarginin in a hydroalcoholic medium. c) Formation of N< alpha >N< omega >bis(N< alpha >acyl-nitroarginin) alpha , omega diaminoalkylamide parting from N< alpha > acyl-nitroarginin and diaminoalkyl, using as condensation agents, such as BOP or DCCD. d) Formation of N< alpha >N< omega >bis(N< alpha >acyl-arginin) alpha , omega , diaminoalkylamide dichlorhydrate by means of a catalytic hydrogenation, in PD/C and formic methanolacid with a proportion comprised between 30-50% of N< alpha >N< omega >bis (N< alpha >acylnitroarginin) alpha , omega , diaminoalkyl. 3.Procedure for the obtention of cationic surfactants according to claim 2, characterized in that for stage a) the following reaction is carried out: disolving hydrochloride of L-arginin in concentrated sufphuric acid, with a proportion of 50% (W,V,), eliminating into space, the formed chlorhydric acid; to this solution is added a quantity of pulverized ammonium nitrate and left to react at least during 15 minutes at room temperature and after removing the gas formed, the mixture is poured on the ground ice and left to cool at 0 DEG C; the solution is brought to 6,8 pH by the addition of concentrated ammonium and maintained at the temperature of 0 DEG C until the total precipitation of the product, approximately 48 hours; the precipitate thus formed, is filtered and crystalized with hot water. 4.Procedure according to claim 2, characterized in that for stage b), a solution is prepared in the range of 0,10-0,30 mole of nitroarginin and Na(OH) in an aqueous solution of 20 to 30% acetone; next, slowly is added an equimolecular quantity of fatty acid chloride, keeping the pH comprised between 11 and 13 by means of the addition of NA(OH). The mixture is maintained under agitation during various hours and HCl is added until an acid ph is reached, when a white precipitate appears, which is filtered, washed with water and ether, and finally, crystalized in ethanol-ether. 5. Procedure according to claim 2, characteriazed in that for stage c) a solution is prepared of 0,30-0,50 mol of N< alpha >-acyl-nitroarginin and excess of terciary organic base (triethylamine or N-methyl morpholine) in chloroform or else, dimethylformamide.To this mixture is added the condensing agent BOP with a concentration comprised between 0,30-0,50 mole and the alkyl diamine in a concentration comprised between 0,15 and 0,25 mol. The reaction mixture is maintained under agitation from 15-30 hours at a temperture comprised between 10 and 25 DEG C, subsequently adding ether, with the appearance of a precipitate which is washed several times with ether. 6. Procedure according to claim 2, characterized in that stage d) is carried out by means of the disprotection of the nitro group for the attainment of the dimers N< alpha >acyl-arginin by a catalytic hydrogenation in a medium which contains PD/C and formic methanol-acid in a proportion comprised between 30-50% in formic acid at a pressure of at least 50 atm, room temperature and in a maximum time of 24 hours. 7. Surfactants according to the previous claims, characterized by their antimicrobial activity versus agents such as, "Alicaligenes faecalis, Bordeltella bronchiseptica, Streptococcus faecalis, Bacilus subtilis, Staphylococcus aereus, Staphylococcus epidermidis and Micrococcus luteus."
