Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
2000-06-23
2002-08-13
Hartley, Michael G. (Department: 1617)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C424S061000, C424S078020, C424S078170, C424SDIG001
Reexamination Certificate
active
06432423
ABSTRACT:
The present invention relates to the use of novel compounds which make it possible in particular to obtain films on a substrate, and to their application in particular in cosmetics or in pharmaceuticals.
Hyperbranched polymers and dendrimers are well known in the prior art. Hyperbranched polymers are molecular constructions having a branched structure, generally around a core. Their structure generally lacks symmetry, the base units or monomers used to construct the hyperbranched polymer can be of diverse nature and their distribution is non-uniform. The branches of the polymer can be of different natures and lengths. The number of base units, or monomers, may be different depending on the different branching. While at the same time being asymmetrical, hyperbranched polymers can have: an extremely branched structure, around a core; successive generations or layers of branching; a layer of end chains.
Hyperbranched polymers are generally derived from the polycondensation of one or more monomers ABx, A and B being reactive groups capable of reacting together, x being an integer greater than or equal to 2, but other preparation processes may be envisaged. Hyperbranched polymers are characterized by their degree of polymerization DP=1-b, b being the percentage of non-terminal functionalities in B which have not reacted with a group A. Since the condensation is not systematic, in contrast with the synthesis of dendrimers, the degree of polymerization is less than 100%. An end group T can be reacted with the hyper-branched polymer to obtain a particular functionality on the ends of chains.
Several hyperbranched polymers can be combined together, via a covalent bond or another type of bonding, by means of their end groups. Such polymers, known as bridged polymers, fall within the definition of the hyperbranched polymers according to the present invention.
Dendrimers are highly branched polymers and oligomers having a well-defined chemical structure. As a general rule, dendrimers comprise a core, a given number of generations of branches, or spindles, and end groups. The generations of spindles consist of structural units which are identical for the same generation of spindles and which may be identical or different for different generations of spindles. The generations of spindles extend radially in a geometrical progression from the core. The end groups of a dendrimer from the Nth generation are the end functional groups of the spindles of the Nth generation or end generation.
The definition of dendrimers given above includes molecules containing symmetrical branching; it also includes molecules containing non-symmetrical branching, such as, for example, dendrimers whose spindles are lysine groups, in which the branching of one generation of spindles on the preceding generation takes place on the &agr; and &egr; amines of lysine, which leads to a difference in the lengths of the spindles of different branching.
Dense star polymers, starburst polymers and rod-shaped dendrimers are included in the present definition of dendrimers. The molecules known as arborols and cascade molecules also fall within the definition of dendrimers according to the present invention.
Several dendrimers can be combined together, via a covalent bond or another type of bonding, by means of their end groups to give species known as bridged dendrimers or dendrimer aggregates. Such species are included in the definition of dendrimers according to the present invention.
Dendrimers can be in the form of an assembly of molecules of the same generation, which are referred to as monodisperse assemblies; they can also be in the form of assemblies of different generations, known as polydisperse assemblies. The definition of dendrimers according to the present invention includes both monodisperse and polydisperse assemblies of dendrimers.
French patent application FR 97/04085 in the name of the Applicant in particular discloses novel polymers chosen from hyperbranched polymers and dendrimers, comprising functional groups corresponding to the following formula:
in which
Y represents an oxygen atom or an NH group,
A represents a linear, branched or cyclic, saturated or unsaturated C
1
-C
12
alkanediyl group, this group optionally being interrupted with one or more hetero atoms and/or substituted with a function chosen from amino, acylamino, carboxylic acid and ester.
These polymers find an application in particular in cosmetics and dermatology as antioxidants or reducing agents.
Now, the Applicant has found, surprisingly, that the said polymers can also be used to allow the preparation of compositions, in particular cosmetic or pharmaceutical compositions, which make it possible to obtain a film when they are deposited on a substrate.
Thus, a subject of the present invention is the use of at least one compound chosen from hyperbranched polymers and dendrimers, comprising at least one group of formula:
in which:
Y represents an oxygen atom or an NH group, and
A represents a linear, branched or cyclic, saturated or unsaturated C
1
-C
12
alkanediyl group, this group optionally being interrupted with one or more hetero atoms and/or substituted with a function chosen from:
amino (—NH
2
),
acylamino (—NH—CO—R) in which R represents a linear, branched or cyclic, saturated or unsaturated C
1
-C
10
alkyl group,
carboxylic acid (—COOH),
ester (—COOR) in which R represents a linear, branched or cyclic, saturated or unsaturated C
1
-C
10
alkyl group, as film-forming agent.
Another subject of the invention is a film-forming composition comprising at least one compound chosen from hyperbranched polymers and dendrimers, comprising at least one group of formula (I), the said composition being able to be obtained by oxidation of a composition comprising at least one polymer chosen from hyperbranched polymers and dendrimers comprising at least one group of formula (II).
Another subject of the invention is the use of at least one polymer chosen from hyperbranched polymers and dendrimers comprising at least one group of formula (II), for the preparation of a film-forming composition comprising at least one compound chosen from hyperbranched polymers and dendrimers comprising at least one group of formula (I), or of a composition as defined above.
Another subject of the invention is a process for obtaining a film on a support, in which a composition as defined above is applied to the said support.
Another subject of the invention is a process for obtaining a film on a support, in which a composition comprising a polymer is applied to the said support, this polymer being chosen from hyperbranched polymers and dendrimers comprising at least one group of formula (II), and the said composition is oxidized during or after its application to the said support.
The prior art discloses a certain number of film-forming agents for obtaining films. In particular, mention may be made of film-forming polymers which may be radical-mediated polymers or polycondensates, among which mention may be made of acrylic polymers and polyurethanes. Such polymers are used in particular in the field of hair care, for example in lacquers, or in the field of make-up, for example in mascaras or nail varnishes in an organic solvent medium.
However, these film-forming agents have certain drawbacks. In particular, these film-forming agents form films as soon as they are deposited on the support.
In contrast, the compounds according to the invention form films only in oxidizing medium. Thus, it is possible to apply an aqueous or aqueous-alcoholic solution, for example, of thiols (II) as a thin layer on a support, and then, at the time chosen, to chemically oxidize or to allow to oxidize freely, in particular in open air, the said thiols into compounds (I), which compounds will form, on drying, on the support, a highly adherent and water-washable film.
The compounds according to the invention allow the production of films similar to those obtained with film-forming polymers of the prior art.
Depending on the oxidation conditions, the quality of the films obtaine
Genard Sylvie
Maignan Jean
Finnegan Henderson Farabow Garrett & Dunner LLP
L'Oreal
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