Use of polyamino acid derivatives as preserving agents,...

Details Use of polyamino acid derivatives as preserving agents,... Use of polyamino acid derivatives as preserving agents,...

2001-01-29

2003-07-01

Dees, Jose′ G. (Department: 1616)

Drug, bio-affecting and body treating compositions

Manicure or pedicure compositions

C424S401000, C424S065000, C424S063000, C514S184000

Reexamination Certificate

active

06585962

ABSTRACT:

The present invention relates to a process for preserving compositions, such as cosmetic and dermatological compositions, which may be intended for topical applications, through the use of certain polyamino acid derivatives.
It is common practice to introduce chemical preserving agents into cosmetic and dermatological compositions, these agents intended to combat the growth of microorganisms in these compositions, which would quickly make the cosmetic and dermatological compositions unsuitable for use. It is especially necessary to protect cosmetic and dermatological compositions against the microorganisms liable to grow inside the compositions and also against those which the user might introduce while handling it, such as when taking up products in jars with the fingers. Chemical preserving agents that are commonly used include parabens and formaldehyde-releasing compounds. However, these preserving agents have a drawback of causing irritation, in particular on sensitive skin, when they are present in relatively large amounts. Other known preserving agents which may be mentioned include organic hydroxy acids. However, these compounds may also cause irritation on account of their desquamating effect on the skin, which is not always well tolerated.
Thus there is a need for preserving agents, such as antimicrobial agents, whose activity is at least as effective as that of the compounds of the prior art, but which do not possess all of the drawbacks of the prior art compounds. Moreover, it would be desirable to make available antimicrobial agents whose antimicrobial spectrum is at least as broad, if not broader, than that of the compounds already known.
One aim of the present invention is thus to propose preserving agents which have a broad antimicrobial spectrum, but which do not possess all of the drawbacks of the prior art.
One subject of the present invention is the use of at least one compound chosen from polyamino acid derivatives corresponding to formula (I) as defined below, and salts thereof, as a preserving agent.
Another subject of the invention is a process for preserving a composition, such as a cosmetic or pharmaceutical composition, comprising introducing at least one polyamino acid derivative of formula (I) as defined below into the composition.
Another subject of the invention is a cosmetic and pharmaceutical composition comprising, in a physiologically acceptable medium, at least one preserving agent chosen from polyamino acid derivatives of formula (I) as defined below and salts thereof.
It has thus been found, surprisingly and unexpectedly, that certain polyamino acid derivatives may have good antimicrobial properties with respect to, for example, viruses, bacteria, yeasts and fungi/molds. On account of their broad antimicrobial spectrum, these derivatives may thus be used, for example, in cosmetic compositions as sole antimicrobial agents, such as antibacterial agents, as antiviral agents, as anti-yeast agents and as antifungal agents. Moreover, these polyamino acid derivatives may be advantageously used as preserving agents in cosmetic and pharmaceutical compositions, such as dermatological compositions.
Advantages of the polyamino acid derivatives according to the present invention, which may be based on their clearly defined and characterized chemical structure, include their manufacture being readily reproducible, and their industrial feasibility being relatively simple. Furthermore, the polyamino acid derivatives according to the present invention have good solubility and compatibility with the media commonly used in cosmetics, for example, aqueous media.
The polyamino acid derivatives used in the context of the present invention are well known in the prior art, including the cosmetics art for their moisturizing properties and for their use in haircare.
Mention may thus be made of Japanese patent application JP-07/041 467, which discloses a class of polyamino acids of high molecular weight consisting essentially of cysteine, as well as the process for preparing these polyamino acids. A class of polyamino acids characterized by the presence of thiol and disulphide functions has also been disclosed in Japanese patent application JP-06/248 072. These polyamino acids react with the thiol linkages of keratin, thus forming disulphide bridges, which makes it possible to increase the sheen and coloration qualities of the hair. Polyamino acids consisting essentially of amino acids with neutral and acidic chains have been disclosed in Japanese patent application JP-04/198 114, along with their use as moisturizing agents.
Mention may also be made of patent application FR-A-2 776 510, which discloses a cosmetic composition intended for reinforcing and caring for keratin fibres, in particular hair fibres, comprising polyamino acid derivatives.
The polyamino acid derivatives used in the context of the present invention correspond to formula (I) below:
in which:
X is chosen from O, S, NH and NR″, wherein R″ is chosen from saturated and unsaturated, linear and branched C
1-6
hydrocarbon-based radicals;
R
1
is chosen from,
i) linear and branched, saturated and unsaturated C
1-40
hydrocarbon-based radicals, optionally substituted with at least one hydroxyl radical and at least one radical —NRR′ and optionally interrupted with at least one hetero atom chosen from N, O and Si, wherein R and R′, which may be identical or different, are chosen from hydrogen and saturated and unsaturated, linear and branched C
1-6
hydrocarbon-based radicals;
ii) radicals of the formula
wherein s may be equal to 0, 1, 2, 3 and 4; and R
4
is chosen from hydrogen and radicals chosen from —NH
2
, —OH, —SH, —CHOHCH
3
, —CONH
2
, —NH—C(NH
2
)═NH, —C
6
H
5
, —C
6
H
4
OH,
iii) radicals of the formula
wherein m may be equal to 3, 4 and 5;
R
2
is chosen from hydrogen; saturated and unsaturated, linear and branched C
1-8
hydrocarbon-based radicals; radicals chosen from —CH
2
C
6
H
5
, —CH
2
C
6
H
4
OH, —CH
2
OH, —CHOHCH
3
, —(CH
2
)
t
—NH
2
wherein t may be equal to 3 and 5;
R
3
is chosen from hydrogen and saturated and unsaturated, linear and branched C
1-6
hydrocarbon-based radicals;
n is an number greater than 1 such that the number average molecular weight of the polyamino acid derivative generally ranges from 100 to 200 000;
wherein the repeating units may be identical or different for the same derivative.
For example, the repeating units may be identical. If the repeating units are different, then at least one of R
2
and R
3
may be varied between the repeating units by choosing at least one of the other meanings given for these radicals.
The salts of the polyamino acid derivatives, such as mineral acid salts and organic acid salts, also form part of the present invention.
According to one embodiment of the present invention, at least one of the following definitions apply to the polyamino acid derivatives:
X is chosen from O, S, NH and NR″, wherein R″ is chosen from saturated and unsaturated, linear and branched C
1-6
hydrocarbon-based radicals;
R
1
is chosen from linear and branched, saturated and unsaturated C
8-40
hydrocarbon-based radicals, optionally substituted with at least one hydroxyl radical and one radical
NRR′ and optionally interrupted with at least one hetero atom chosen from N, O and Si, wherein R and R′, which may be identical or different, are chosen from hydrogen and saturated and unsaturated, linear and branched C
1-6
hydrocarbon-based radicals;
R
2
is hydrogen;
R
3
is chosen from saturated, linear and branched C
1-6
hydrocarbon-based radicals; such as, for example, methyl and ethyl radicals; and
n is chosen from a number ranging from 2 to 100, or is chosen from a number such that the number average molecular weight of the polyamino acid derivative generally ranges from 150 to 10,000. In certain embodiments, each of these definitions apply.
In another embodiment of the present invention, at least one of the following definitions apply to the polyamino acid derivatives:
X is chosen from O, S and NH;
R
1

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