Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1986-10-03
1989-07-04
Griffin, Ronald W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
514 55, 514844, 424 47, 424 70, 424 71, 424401, 424DIG1, 424DIG2, C08B 3708, A61K 706, A61K 748
Patent
active
048452041
DESCRIPTION:
BRIEF SUMMARY
The invention is directed to cosmetic compositions for the treatment of hair, particularly compositions for strengthening the hairstyle, or the skin, comprising a content of new macromolecular compounds derived from chitosan in a suitable cosmetic base.
The invention is directed, further, to the new chitosan derivatives and to processes for the production thereof.
The hair and hairstyle strengtheners currently found on the market usually contain synthetic resins, which can possibly be washed out, such as polyvinyl pyrrolidone, copolymers of vinyl pyrrolidone with vinyl acetate, terpolymers of vinyl acetate with other monomers, polyacrylates and polymethacrylates and their copolymers with other monomers.
When used in hairspray recipes, the above polymers have various disadvantages. Thus, the solvents often remain for a very long time in the resin film applied to the hair, so that a relatively long drying time is necessary, and the hair feels sticky immediately after spraying on the hairspray.
In addition, the use of most of these polymers leads to a substantial interlacing of the surface of the hairstyle (so-called helmet formation), which gives the hair an unnatural appearance and a rough feel.
In addition, with most of the aforementioned polymers the ability to comb out the hair after application is considerably impaired, and the hairstyling is very difficult because of excessive electrostatic charge.
In recent times, halogen-containing propellant gases have been increasingly replaced by those that are halogen-free for ecological reasons. However, it has been established that the majority of the mentioned polymers are not suited for this purpose. Thus, precipitation of the polymers can occur during storage so that the sprays are unusable.
It has already been attempted to overcome the aforementioned disadvantages by using water soluble salts of chitosan, a polyglucosamine producible by means of deacetylation of chitin, in such cosmetic compositions. In this connection, reference is made to the present author's patents EP-PS 0 002 506 and DE-PS 2 627 419.
However, the chitosan is insoluble in anhydrous preparations, such as in anhydrous aerosol hairsprays on the basis of organic solvents in particular, and can therefore not be used in the latter. Another disadvantage of the chitosan consists in that it is insoluble in neutral or alkaline hydrous solution, so that it is not possible to apply it, for example, in alkaline permanent wave agents or hair coloring agents.
Chitosan derivatives which are soluble in organic solvents are not mentioned in the literature on the subject with very few exceptions (see, e.g. Fujii et al., Carbohydr. Res. 83, pages 389-393 (1980)).
It has no been found that chitosan can be reacted in a simple manner in mixed ether derivatives with interesting characteristics by means of two alkylation steps which are carried out one after the other or simultaneously.
The N-hydroxypropylation necessary for this purpose and the subsequent O-alkylation lead to modified, natural polymers which are distinguished particularly by their favorable solubility in organic solvents, in addition to their water solubility in the acid pH range. Accordingly, the subject matter of the invention consists in new macromolecular, polymeric compounds derived from chitosan which are obtained in this manner and have the general formula I (R.sup.3).sub.q ].sub.p H (I), desired numerical value from 0.5 to 10, q is a desired numerical value from 0.5 to 4.0, p denotes an integer from 50 to 5000, R.sup.1 designates an acetyl group, R.sup.2 denotes a bivalent group ##STR2## and R.sup.3 denotes a straight-chain or branched alkyl radical with 1 to 6 carbon atoms, or their salts with an organic or inorganic acid.
The expression in brackets in formula I shows repeatedly substituted glucosamine monomer units.
In formula I the symbols n and q preferably have the meaning, n=1 to 3 and q=1 to 3.6, while the limiting viscosity number of the chitosan derivatives is preferably in the range of 14 to 44 ml/g.
Of the chitosan derivativ
REFERENCES:
patent: 3879376 (1975-04-01), Vanlerberghe et al.
patent: 4528283 (1985-07-01), Lang et al.
Chem. Abstracts, vol. 98, No. 22, May 22, 1983 abstract 181486e.
Bull. Chem. Soc. of Japan, Band 26, Nr. Apr. 3, 1953, R. Senzyu: "Untersuchungen uber Lignin und Zellstoff. II. Eine neue Bestimmungsmethode des Lignins in Holzern und Zellstoffen durch Kolloidtitration", Seiten 148-153, siehe Seite 148, Versuchsteil.
Breuer Lothar
Hoch Dietrich
Konrad Eugen
Lang Gunther
Lenz Hans-Rudi
Griffin Ronald W.
Striker Michael J.
Wella Aktiengesellschaft
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