Colloid systems and wetting agents; subcombinations thereof; pro – Continuous liquid or supercritical phase: colloid systems;... – Primarily organic continuous liquid phase
Reexamination Certificate
2000-09-12
2002-05-14
Metzmaier, Daniel S. (Department: 1712)
Colloid systems and wetting agents; subcombinations thereof; pro
Continuous liquid or supercritical phase: colloid systems;...
Primarily organic continuous liquid phase
C516S069000, C516S915000, C424S401000, C424S070310, C514S938000, C514S939000, C536S055200
Reexamination Certificate
active
06387961
ABSTRACT:
The present invention relates to novel active compounds, their preparation and their use in the field of cosmetic and of pharmaceutical dermatology. In particular, the present invention relates to active compounds and cosmetic and dermatological preparations comprising such active compound combinations. In particular, the present invention relates to active compounds which have surfactant properties. The invention further relates to cosmetic and dermatological preparations which contain such substances. In a preferred embodiment, the present invention relates to cosmetic cleansing agents.
Agents of this type are known per se. In this context, they are essentially surface-active substances or substance mixtures which are offered to the consumer in various preparations.
Preparations of this type are, for example, bubble baths and shower baths, solid and liquid soaps or so-called “syndets” (synthetic detergents), shampoos, hand-washing pastes, intimate cleansing agents, special cleansing agents for infants and the like.
Surface-active substances—the best-known of which are the alkali metal salts of the higher fatty acids, i.e. the classical “soaps”—are amphiphilic substances which can emulsify organic non-polar substances in water.
These substances wash not only dirt from the skin and hair; depending on the choice of the surfactant or of the surfactant mixture, they irritate the skin and mucous membranes to a greater or lesser degree. The most useful surfactant for cosmetic cleansing agents is sodium lauryl ether sulphate. Although it has good washing power and—depending on dosage—is very highly skin- and mucous membrane-tolerable, sensitive persons should avoid frequent contact with it.
There are admittedly a large number of very mild surfactants available, but the surfactants of the prior art are either mild, but cleanse poorly, or else they cleanse well, but irritate the skin or mucous membranes.
Cosmetic emulsions also contain interfacially active substances, so-called emulsifiers. These reduce the surfaces of contact between the phases and form oil/water interfacial films on the phase boundary. As a result, the irreversible confluence of the dispersed phase is counteracted.
Efficient emulsifiers are therefore distinguished by a very good emulsifying, solubilizing and dispersing ability. To a great extent, it is desirable that such substances do not cause skin irritation. The choice of such substances known to the prior art is restricted. It was therefore an object of the present invention to enrich the prior art in this respect.
Advantageous cleansing formulations, even within the meaning of the present invention, are shower preparations.
Preparations of this type are known per se. In this context, they are essentially surface-active substances or substance mixtures which are offered to the consumer in various preparations. Preparations of such a type are in general distinguished by a high water content to a greater or lesser degree, but can also be present, for example, as a concentrate.
In general, preparations which are intended for the shower bath do not differ or hardly differ from bath preparations apart from the fact that in the case of shower preparations products of higher viscosity are preferred, which do not run from the hand after removal from the container. In the case of bath preparations, this is less of practical importance.
Even in the case of a simple water bath without addition of surfactants, a swelling of the horny layer of the skin first occurs, the degree of this swelling, for example, depending on the duration of the bath and its temperature. At the same time, water-soluble substances, e.g. water-soluble dirt constituents, but also substances endogenous to the skin, which are responsible for the water-binding power of the horny layer, are washed off or washed out. As a result of surface-active substances endogenous to the skin, skin oils are additionally also dissolved to a certain extent and washed out. After initial swelling, this causes a subsequent marked drying out of the skin, which can be increased by detergent additives.
In healthy skin, these processes are in general unimportant, as the protective mechanisms of the skin can compensate for such slight disturbances of the upper skin layers without problem. However, even in the case of non-pathological variations from the normal status, e.g. as a result of environmentally related wear and tear and irritations, damage due to light, presbyderma, etc., the protective mechanism of the skin surface is disturbed. Under certain circumstances, it is then no longer able by itself to fulfill its objects and must be regenerated by external measures.
The prior art is acquainted with oil bath preparations of various types, it being possible to vary the properties of the fat or oil phase by addition of surface-active substances. In this case, depending on the nature and amount of the constituents chosen, preparations can be formulated which either produce spreading oil films, oil-in-water systems or even total solubilizates on the bath-water surface. Foaming formulations, but also only slightly foaming or non-foaming formulations, are possible. In general, the functionality of preparations of this type is restricted in oil bath or oil cream bath preparations to the refatting or superfatting of the uppermost layers of skin.
Nevertheless, caring oils can in isolated cases at best cover up the harmful effect of a not very skin-friendly surfactant, which is why an oil bath or an oil cream bath cannot be better than the surfactant(s) employed therein.
It was thus the object of the present invention to remedy the defects of the prior art in this respect.
In a further preferred embodiment, the present invention relates to cosmetic and dermatological preparations for the prophylaxis and treatment of cosmetic or dermatological cell changes, in particular skin changes such as, for example, skin ageing, in particular the cell ageing caused by oxidative processes, in particular skin ageing.
Finally, it was an object of the present invention to conceive preparation processes for such active compounds.
It was surprising and not to be foreseen by the person skilled in the art that alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids of the general formula
where R is representative of the group consisting of branched and unbranched alkyl of 1-48 C atoms, in particular of 14-22, preferably 16-18, C atoms, and their salts, and a process for the preparation of alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids of the general formula
where R is representative of the group consisting of branched and unbranched alkyl of 1-48 C atoms, in particular of 14-22, preferably 16-18, C atoms, and their salts, characterized in that
(1) chitin is ground
(2) the ground chitin is treated with acid and a first aliphatic alcohol of low chain length, preferably of a chain length of less than C
8
, whereupon
(3) if desired the reaction product thus obtained is purified by dialysis, preferably electrodialysis,
(4) a second alcohol not identical to the first aliphatic alcohol, preferably of a chain length of C
8
and longer, is reacted with the reaction product under acid catalysis, whereby the first aliphatic alcohol becomes free again and (4a) if desired is removed by distillation,
(5) the reaction product is subjected to oxidation,
and the alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids or their salts obtained in this process and the novel intermediates in this process eliminate all outlined disadvantages of the prior art.
Consequently, also according to the invention is the use of alkyl 2-acetamido-2-deoxy-D-glucopyranaside uronic acids of the general formula
(&bgr;-glycosidic form) (&agr;-glycosidic form)
where R is representative of the group consisting of branched and unbranched alkyl of 1-48 C atoms, in particular of 14-22, preferably 16-18, C atoms, as surface-active and/or interfacially active active compounds, in particular as detergent surfactants or emulsifiers, and where the uronic acids can preferably be present
Scheel Oliver
Schmidt-Lewerkühne Hartmut
Schneider Günther
Thiem Joachim
Metzmaier Daniel S.
Norris & McLaughlin & Marcus
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