Microcapsules with a wall of crosslinked plant polyphenols and c

Details Microcapsules with a wall of crosslinked plant polyphenols and c Microcapsules with a wall of crosslinked plant polyphenols and c

1995-09-27

1998-07-14

Page, Thurman K.

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Particulate form

4241951, 424401, 424451, 424455, 424499, 424500, 424501, 5147723, 514773, 514774, 514775, 514776, 514777, 514778, 514779, 514781, 514782, 514783, 514801, 514844, 514952, 514962, 264 432, 4284022, A61K 950, A61K 3578

Patent

active

057800600

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/FR 95/00116 filed Feb. 1, 1995. containing them
The present invention relates essentially to the application, to plant polyphenols, of interfacial crosslinking by means of a crosslinking agent to form microcapsules, to the microcapsules produced in this way, to the processes for their manufacture and to the compositions containing the microcapsules obtained in this way, such as cosmetic, pharmaceutical, food and dietetic compositions.
Plant polyphenols constitute an important group of natural substances with well-known anti-free radical and antioxidizing properties (see for example: "Polyphenolic Phenomena", A. SCALBERT, Editor, INRA Editions, Paris, 1993). These compounds, including especially flavonoids such as, for example, procyanidolic oligomers or PCO, possess valuable biological properties associated in particular with their anti-free radical activity. For example, they are capable of preventing the harmful effects of free radicals on the skin and hence of playing a protective role against solar radiation and against ageing of the skin, and an anticarcinogenic role. They can also prevent erythema and couperose. Moreover, they possess properties which can be utilized in therapeutics, in particular in dermatology and for applications to the mucous membranes, such as antiinflammatory properties, vasculoprotective properties (treatment of ecchymoses, petechiae, gingivorrhagia, epistaxis, etc.) and antiallergic, antiulcer, antibacterial, antiviral and anticancer properties. Finally, when added to foods or dietetic products, they can preserve the preparations in which they are incorporated, by their antioxidizing action, and at the same time constitute a valuable supply of anti-free radical substances, making it possible to prevent diseases due to free radicals, such as cancer.
Thus they have applications especially in the fields of cosmetics, pharmaceutics, food and dietetics. However, it is often impossible to incorporate them into certain preparations, such as preparations for cosmetic or dermatological use for example, because of the dark coloration which these relatively unstable substances impart to said preparations.
Likewise, anthocyanin derivatives, which are colored polyphenolic substances also belonging to the flavonoid group (F. J. Francis, Crit. Rev. Food Sci. Nutri., 1989, 28, 273-314), also exhibit an anti-free radical activity and possess valuable biological properties, especially on the permeability and strength of the hair. However, they cannot generally be incorporated into certain preparations, such as preparations for cosmetic or dermatological use for example, because of their high tinctorial strength.
It is known that high-molecular polymers can be prepared by the interfacial polycondensation of a synthetic diphenol, namely bisphenol A, with diacid chlorides (W. M. Eareckson, J. Polymer Sci., 1959, 40, 399-406). On the basis of this principle, S. Suzuki et al. (Chem. Pharm. Bull., 1968, 6, 1629-1631) obtained microcapsules by applying the polycondensation reaction of bisphenol A with sebacoyl chloride to an emulsion.
However, no document in the prior literature describes the preparation of microcapsules by the interfacial crosslinking of plant polyphenols.
Within the framework of the invention, it has been discovered, unexpectedly, that the interfacial crosslinking of plant polyphenols, particularly flavonoids, by means of a crosslinking agent, preferably a diacid halide and particularly a diacid chloride, gives a product, especially microcapsules, which is particularly stable, notably in the presence of an aqueous medium, while at the same time preserving the initial activity of these plant polyphenols, in particular a biological activity and especially an anti-free radical activity, which is particularly remarkable.
Thus it has been observed, unexpectedly, that the interfacial acylation of phenolic groups of the plant polyphenol forms ester bonds and gives membranes of crosslinked polyphenol, while at the same time leaving a sufficient number of ph

REFERENCES:
patent: 4780321 (1988-10-01), Levy et al.

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