Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
2002-04-09
2003-12-09
Badio, Barbara P. (Department: 1616)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C424S400000, C424S059000, C552S218000, C552S219000, C514S580000, C514S588000, C514S844000
Reexamination Certificate
active
06660284
ABSTRACT:
The invention relates to a novel family of anthraquinone compounds, to a process for manufacturing them and to their use as pigments, especially in cosmetics. The invention is also directed toward cosmetic compositions containing them.
In the literature, the synthesis of colorants with an anthraquinone nucleus, in particular those substituted with amines, is well known. One synthesis is especially described in FR 2 039 381. Some of these colorants, such as those described in U.S. Pat. No. 5,486,629, are used for dyeing the hair.
These colorants are generally soluble in water or in apolar media (organic solvents and oils). They therefore cannot be used as insoluble pigments in applications such as skin makeup, since a leaching phenomenon is observed.
Consequently, this family of colorants has very little potential for industrial development as pigments, although certain polymerization processes, for instance the one described in U.S. Pat. No. 4,279,662, or complex treatment processes such as the one described in FR 2 060 730, have attempted to improve this persistent problem.
The inventors have discovered a novel family or anthraquinone compounds containing urea bonding which may be used as pigments, in particular in cosmetic compositions. These compounds, which are the subject of the invention, are insoluble or very sparingly soluble in aqueous media, and also in organic solvents and oily media. They may thus solve the problem of leaching observed with the anthraquinone colorants of the prior art in these media, and in particular in oily media.
In addition, these novel compounds are very accessible since they are prepared in a single step that is easy to carry out.
One subject of the present invention is thus novel anthraquinone compounds of formula (I) below.
Another subject of the invention is a process for manufacturing these novel compounds.
Yet another subject of the invention is the use of these compounds as pigments, especially in cosmetics.
A subject of the invention is also cosmetic compositions containing them.
Other subjects, characteristics, aspects and advantages of the invention will emerge even more clearly on reading the description and the various examples that follow.
According to the invention, the novel compounds correspond to the general formula (I):
in which:
m and n, which may be identical or different, are between 1 and 20;
X and Z each represent NH or O;
p is 0 or 1;
Y represents a carbon atom or a sulphur atom;
R
1
, R′
1
, R
5
, R′
5
, R
6
, R′
6
, R
7
, R′
7
, R
8
, R′
8
, R
9
, R′
9
, R
10
and R′
10
, which may be identical or different, each represent a hydrogen atom, a halogen atom, a linear or branched, saturated or unsaturated C
1-8
hydrocarbon-based group, a hydroxyl group,
and R
2
, R
3
, R
4
, R′
4
and R
11
, which may be identical or different, each represent a hydrogen atom, a linear or branched, saturated or unsaturated, optionally hydroxylated, C
1-8
hydrocarbon-based group.
The hydrocarbon-based groups that are suitable in the present invention are linear or branched, saturated or unsaturated and contain from 1 to 8 carbon atoms and preferably from 1 to 4 carbon atoms.
Hydrocarbon-based groups that may especially be mentioned include alkyl, alkenyl or alkynyl groups such as, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methylene, ethenyl or ethynyl groups.
Halogen atoms that may especially be mentioned include chlorine, bromine, fluorine and iodine atoms, and preferably the chlorine atom.
The preferred compounds of the invention are those corresponding to formula (I) in which n=m, R′
1
=R
1
, R′
4
=R
4
, R′
5
=R
5
, R′
6
=R
6
, R′
7
=R
7
, R′
8
=R
8
, R′
9
-R
9
and R′
10
=R
10
, Z=X and p=1, and the compounds that are more particularly preferred correspond to the general formula (II) below:
in which:
n is from 1 to 12,
R
1
represents a hydrogen atom, a halogen atom, a linear or branched, saturated or unsaturated C
1
-C
8
hydrocarbon-based group, a hydroxyl group or a group —NR
2
R
3
,
R
2
, R
3
and R
4
each represent a hydrogen atom or a linear or branched, saturated or unsaturated C
1
-C
8
hydrocarbon-based group, and
R
5
and R
6
each represent a hydrogen atom, a halogen atom, a linear or branched, saturated or unsaturated C
1
-C
8
hydrocarbon-based group or a hydroxyl group.
Examples of compounds of formula (I) or (II) above that may especially be mentioned include 1,3-bis[3-(9,10-dioxo-9,10-dihydroanthracen-1-ylamino)propyl]urea and 1,3-bis[3-(4-methylamino-9,10-dioxo-9,10-dihydro-anthracen-1-ylamino)propyl]urea.
Another subject of the present invention is the process for manufacturing the compounds of formula (I) above.
This process consists in reacting an anthraquinone derivative of general formula (III) with an anthraquinone derivative of general formula (IV):
in which A represents an activating group such as, especially, a group derived from imidazole or a halogen atom, the other symbols having the same meaning as for formula (I);
in which R
1
, R
4
to R
10
, Z and n have the same meaning as for formula (I)
in the presence of a solvent and optionally a base, at a temperature from 0 to about 160° C. for about 30 minutes to about 20 hours.
The solvents that are suitable in the present invention are preferably dipolar aprotic solvents such as, for example, N,N-dimethylacetamide or N,N-dimethyl-formamide.
The bases that may be used are especially chosen from pyridine or its derivatives, triethylamine and diisopropylethylamine.
One preferred manufacturing process of the invention makes it possible to obtain compounds of formula (I) above in which R′
1
=R
1
, R′
4
=R
4
, R′
5
=R
5
, R′
6
=R
6
, R′
7
=R
7
, R′
8
=R
8
, R′
9
=R
9
and R′
10
=R
10
, n=m, Z=X and p=1. It makes it possible, inter alia, to obtain the particularly preferred compounds of formula (II) above.
The process consists in reacting an anthraquinone derivative of general formula (IV):
in which n, Z, R
1
and R
4
to R
10
are as defined above for formula (I), or one of its salts,
with phosgene or one of its derivatives or of its substitutes, or instance carbonyldiimidazole, at a temperature from 0 to about 160° C. for about 30 minutes to about 20 hours in the presence of a solvent as defined above, and optionally of a base as described above.
The invention also relates to the use as a pigment of at least one compound of formula (I) or (II) as defined above, and preferably 1,3-bis[3-(9,10-dioxo-9,10-di-hydroanthracen-1-ylamino)propyl]urea and 1,3-bis[3-(4-methylamino-9,10-dioxo-9,10-dihydroanthracen-1-ylamino)propyl]urea.
This novel family of pigments may be used in the food and cosmetics sectors and in paints, and preferably in cosmetics.
The cosmetic composition according to the invention comprises, in a cosmetically acceptable medium, at least one compound of formula (I) or (II) as defined above. This compound is especially present in an amount of between 0.01% and 50% by weight and preferably between 0.1% and 25% by weight relative to the total weight of the composition.
The expression “cosmetically acceptable medium” means a medium that is compatible with all keratin materials such as the skin, the nails, the hair, the eyelashes, the eyebrows and the lips, and any other area of body or facial skin.
The medium may comprise or be in the form of, for example, a suspension, a dispersion, a solution in a solvent or an aqueous-alcoholic medium, optionally thickened or even gelled; an oil-in-water, water-in-oil or multiple emulsion; a gel or a mousse; an emulsified gel; a dispersion of vesicles, especially a lipid dispersion; a two-phase or multiphase lotion; a spray, a free, compact or cast powder; or an anhydrous paste.
A person skilled in the art may select the appropriate presentation form
Bordier Thierry
Philippe Michel
Badio Barbara P.
L'Oreal
Price D. Douglas
Steptoe & Johnson LLP
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