Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Radical -xh acid – or anhydride – acid halide or salt thereof...
Reexamination Certificate
2001-02-05
2002-06-25
Cook, Rebecca (Department: 1614)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Radical -xh acid, or anhydride, acid halide or salt thereof...
C514S881000
Reexamination Certificate
active
06410593
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel compositions which are useful in cosmetology, in particular shampoos and foaming gels, which are intended to care for the hair and/or the scalp, in particular to combat dandruff or to prevent its formation. The invention is directed towards shampoos whose washing base contains an amphoteric surfactant and an anionic surfactant, where appropriate supplemented with a thickener and/or a hair conditioner.
BACKGROUND OF THE INVENTION
In shampoos whose washing base contains an anionic surfactant and an amphoteric surfactant, the washing function itself is based on the two components, but a foaming function is provided by the amphoteric surfactant. In very general terms, the amphoteric surfactant is an alkylbetaine, in particular a lauric-, coconut- or palm kernel-based alkylamidopropylbetaine. The mechanical elimination of dandruff, the causative agent of which is a fungus,
Pityrosporum ovalae
, is one of the expected results of shampooing, but it has also been sought to develop shampoos which combat or prevent the formation of dandruff. For this, use has been made of various antifungal agents.
Among the standard antifungal agents, mention may be made of:
preserving agents whose fungal spectrum is oriented towards fungi and particularly yeasts, such as sorbic acid and dehydroacetic acid,
active agents listed as anti-yeast agents, such as zinc pyrithione, piroctone-olamine and climbazole,
a few surfactants derived from undecylenic acid, in particular 4-sulpho-{2-[(1-oxo-10-undecenyl)amino]ethyl}butanedioic ester, disodium (RN=26650-05-5) (or disodium undecylenamido MEA sulphosuccinate, according to the CTFA name adopted in the International Cosmetic Ingredient Dictionary, 6th edition, by The Cosmetics, Toiletry and Fragrance Association, 1995), and N-(2-hydroxyethyl)undecenamide (RN=20545-92-0 and 40839-40-5) (CTFA : undecylenamide MEA).
However, some antifungal active principles among those most commonly used show cytotoxic potential in vitro. It is necessary to lower the working amounts thereof to below an acceptable cytotoxicity threshold, or even to combine them with molecules which protect the integrity of skin cells which are damaged or inflamed to a greater or lesser extent. These products have other drawbacks: for example, piroctone-olamine poses coloration problems in shampoos containing this active principle, zinc pyrithione is a water-insoluble powder which leads to opaque formulations that are unstable in light, climbazole is water-insoluble and requires the mandatory use of solvents (ethanol, benzyl alcohol).
As regards the undecylenic acid derivatives, some have already been cited for their antibacterial and antifungal activity, in particular the zinc salts of undecylenamido MEA sulphosuccinate (WO 97/18823 of 29.05.97 from Pièrre Fabre; EP 23676 of 11.02.81 from Rewo) and of tricarboxylic acid which are derived from the product of the Diels-Alder reaction between maleic anhydride and undecylenic acid (EP 71025 of 9.02.83 from Grillo Werke AG), as well as a number of esters (JP 08/053,326 of 27.02.96 from Kanebo; EP 28459 of 13.05.81 from Imperial Chemical Industries Ltd.). As examples, among the most common undecylenic acid derivatives are found N-(2-hydroxyethyl)undecenamide (CTFA : undecylenamide MEA) and 4-sulpho-{2-[(1-oxo-10-undecenyl)amino]ethyl}butanedioic ester, disodium (CTFA: disodium undecylenamido MEA sulphosuccinate), which are sold, respectively, under the trade names “Rewocid®U185 or Witcamide®6570” and “Rewocid®SB U185” by the company Witco. However, these derivatives are not amphoteric.
It has been discovered, unexpectedly, that in addition to the usual characteristics of betaines (co-surfactant, good foaming power, mild detergent), N-(carboxymethyl)-N,N-dimethyl-3-[(1-oxoundecenyl)amino]-1-propanaminium hydroxide (RN=98510-75-9, neutral zwitterionic form) or CTFA: undecylenamidopropylbetaine
has antifungal activity towards
Pityrosporum ovalae
and thus develops antidandruff efficacy which has never been cited to date. Consequently, it offers the very great advantage of being able to constitute an amphoteric component of a shampoo which itself has the desired antidandruff properties. This discovery is exploited in shampoos of the invention, which are essentially aqueous compositions of a washing base consisting of amphoteric surfactants and anionic surfactants and whose amphoteric surfactants do themselves—and this is the characteristic of the invention—partly consist of undecylenamidopropylbetaine.
For the purposes of the invention, the term anionic surfactant is understood to refer to one or more compounds taken from the group formed of (C
10
to C
14
)alkyl sulphates and (C
10
to C
14
)alkyl ether sulphates. Lauryl ether sulphates are anionic surfactants used commonly by shampoo formulators.
For the purposes of the invention, the term amphoteric surfactant is understood to refer to the compounds chosen, alone or as a mixture, from alkyl amphocarboxyglycinates, alkyl amphocarboxypropionates, alkyl amphodiacetates, alkyl amphodipropionates, alkyl amphoglycinates, alkyl amphopropionates, alkyl iminopropionates, alkyl iminodipropionates, alkyl amphopropylsulphonates, alkylbetaines, alkylamidopropylbetaines, alkylsultaines and alkylamidopropylhydroxysultaines. In this list, alkyl is understood in the sense of C
10
to C
14
hydrocarbon-based chains and more especially lauric, coconut or palm kernel fatty acid residues or equivalent sources. Cocoamidopropylbetaines are amphoteric compounds that are preferred for preparing the formulations according to the invention.
Undecylenamidopropylbetaine, which is the characteristic amphoteric compound of the invention, is an undecylenic-based alkylamidopropylbetaine. It can be prepared according to processes known to those skilled in the art, in particular by following the procedure described in U.S. Pat. No. 3,225,074 (American Cyanamid) which consists in reacting undecylenic acid with N,N-dimethyl-1,3-propanediamine (DMAPA) between 140 and 200° C., followed by reacting the tertiary amidoamine
thus obtained with monochloroacetic acid in the presence of an alkaline salt or the corresponding salt of this acid, the reaction being carried out in aqueous medium. The alkali metal chloride, usually sodium chloride, co-produced during the reaction is generally left in this aqueous betaine solution.
The compositions of the invention are aqueous solutions in which the content of all of the constituents of the washing base (amphoteric and anionic compounds) lies within certain limits so as to ensure their physical equilibrium, in particular their homogeneity and their transparency (in the absence of the intentional introduction of pearlescent agents), these limits naturally being capable of varying to a certain extent depending on the individual components used, which will be represented by the following symbols: An used for anionic components, Amph for amphoteric compounds, &Sgr;Amph representing all of the amphoteric compounds, AmphU representing undecylenic betaine, Amph* representing the amphoteric components except for undecylenic betaine.
This gives, on the one hand, as regards the anionic components/amphoteric compounds equilibrium:
12.5%≦An+&Sgr;Amph≦17.6
5%≦An≦15
3.5%≦&Sgr;Amph≦9.2
on the other hand, as regards the amphoteric compounds/undecylenic amphoteric component equilibrium:
3.5%≦&Sgr;Amph≦9.2
2%≦Amph*≦7
1.5%≦AmphU≦3.5
A common shampoo composition according to the invention will have, for example, the general composition
Sodium lauryl ether sulphate
5 to 15%
Cocoamidopropylbetaine
2 to 7%
Undecylenamidopropylbetaine
1.5 to 3.5%
Ordinary ingredients of shampoo formulations and
qs 100%
demineralized water
The common ingredients in the formulation of products of this type form part of these compositions, namely:
thickeners intended to give the shampoos a sufficient consistency and improved cosmetic qualities. Among the known thickeners,
De Mesanstourne Regine
Le Gall Hélène
Lebon Hélène
CECA S.A.
Cook Rebecca
Smith , Gambrell & Russell, LLP
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