Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Patent
1996-12-13
1999-11-30
Kumar, Shailendra
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
424 7803, 424405, 510131, 510382, 510383, 514 19, 514 20, 564153, 564159, A61K 3116, C07C23304, A01N 3718
Patent
active
059944064
DESCRIPTION:
BRIEF SUMMARY
INTRODUCTION
As is well known, the surfactants are organic molecules which contain two functional groups with opposed characteristics. A conventional surfactant contains an absorbent group (water soluble) and a hydrophobic group (insoluble in water) both in the same molecule. This structure is known as amphiphilic structure.
Though at present it may be considered that the industry has available the suitable surfactants, the ecological demands, currently force research and development of new alternatives which protect and improve the environment and quality of life.
Numerous structural modifications have been made to improve the biocompatibility of these compounds, either parting from natural raw materials such as aminoacids and/or sugars, or by increasing the hydrophobic interaction of these compounds in an intent to potentiate their surface activity and in consequence their efficiency.
Among the numerous structural modifications described in literature, the following deserve our attention; those which give arise to dimeric or geminal surfactants characterized by containing in the same molecule, two or more hydrophobic chains together with various ionic groups. It is described that such structures reinforce the intra or intermolecular hydrophobe interactions, with the consequent result of different highly efficient surfactants and in some cases with excellent aqueous solubility properties.
These materials have demonstrate that they have unforeseeable physico-chemical properties (i.e. extremely low CMCs and great absorbant effectivity on the surfactants) which consequently contributes to optimize the environmental aspects of the surfactants.
Among the ionic geminal surfactants, the bicationic quaternary ammonium salts must be highlighted, which are also known as bis-QUATS, for their excellent antimicrobial properties, especially versus Gram negative bacteria, when compared with the classical mono-QUATS. However, since they are quaternary ammonium salts, it is known that they are resistant to biodegradation and in consequence their ecological acceptability is questioned.
The present invention pretends to overcome this aspect by dimerizing ecologically acceptable cationic surfactants, such as the monocatenaries y derivatives of the N.sup..alpha. -acyl-arginin. The new structure shall present the double advantage of being efficient as regards surface (due to its geminal structure) and biodegradable (since it is an aminoacid derivate).
PRIOR ART TO THE INVENTION
Though the literature includes a great variety of descriptions on antimicrobial surfactants with geminal bicationic structures, the compounds which are the object of the present patent are a novelty and no similar reference is described in the same. The novelty of the present invention is the result of the combination of one same molecule with two residues of N.sup..alpha. -acyl-arginin in one geminal mimetic structure to the bis-QUATS.
The synthesis and development of the monocatenary derivatives of the N.sub..alpha. -acylarginin have been carried out by our team after many years of study, which has originated a great number of results and publications (Spanish Patent 512.643; M. R. Infante, J. Molinero and P. Erra, JAOCS, Vol.69, N97, 1992; J. Molinero, M. R. Julia, P. Erra, M. Robert and M. R. Infante, JAOCS, Vol. 65, No. 6 1988; C. Solans, M. A. Pes; N. Azemar and M. R. Infante, Progr. Colloid Polym Sci81.pp 144-150, 1990).
On the other hand, since the 50's, numerous bifunctional structures are known, of the type bis-QUATS ((A) C. A. Bunton, L. Robinson, J. Schaak and M. F. Stam, J. Org. Chem., 1971, 36, 2346; (b) R. Zana, M. Benrraou and R. Rueff, Langmuir, 1991,. 7.1072; (c) F. Dvinski, L. Lacko and T. Imam, J. Colioid Interface Sci., 1991, 143,336; (d) R. Zana and Y. Talmon, Nature, 1993,. 362.228; (f) H. C. Parreira, E. R. Lukenbach and M. K. Lindemann, J. Am. Oil chem. SOC., 1979, 56,1015) the formula of which could be the diagram according to I. ##STR2##
These compounds contain per molecule two hydrophobic chains, two groups of quaternary
REFERENCES:
Infante et.al,JAOCS, vol. 69, No. 7, pp. 647-652, 1992.
Infante Martinez-Pardo Maria Rosa
Perez Munoz Lourdes
Consejo Superior Investigaciones Cientificas
Kumar Shailendra
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