Drug – bio-affecting and body treating compositions – Live skin colorant containing
Reexamination Certificate
2000-04-21
2002-04-16
Dees, Jose' G. (Department: 1616)
Drug, bio-affecting and body treating compositions
Live skin colorant containing
C424S059000, C424S061000, C424S064000, C424S070700, C424S070900, C424S401000
Reexamination Certificate
active
06372202
ABSTRACT:
The present invention relates to cosmetic compositions comprising a novel orange pigment with an intense and saturated color which does not generate free radicals and more especially to compositions for making up the skin, both of the human face and of the human body, superficial body growths, such as the nails or keratinous fibres, such as the eyelashes, eyebrows or hair, and lips.
Make-up compositions, such as loose or compacted powders, foundations, blushers, eyeshadows, lipsticks, concealers, mascaras, eyeliners, lip pencils, eye pencils or nail varnishes and products for making up the body are composed of an appropriate vehicle and of coloring agents of various natures intended to confer a certain color on these compositions, before and/or after their application to the skin, lips and/or superficial body growths.
These coloring agents can be lakes, inorganic or organic pigments and/or pearlescent pigments, or dyes. In the range of orange pigments, cosmetic technologists have available pigments of inorganic origin, such as brown-yellow iron oxides or mixtures of brown-yellow iron oxides, and pigments of organic origin. Inorganic pigments, in particular inorganic oxides, have the advantage of being very stable but have the disadvantage of giving rather dull and pale colors. Organic lakes have the advantage of conferring vivid colors on the compositions but are generally unstable with regard to light, temperature or pH. Some of these lakes also exhibit the disadvantage of staining the skin in an unsightly way after application by bleeding of the dye. Pearlescent pigments, for their part, make it possible to obtain varied but never intense colors with iridescent but generally fairly weak effects.
Furthermore, some coloring agents exhibit the disadvantage of generating free radicals in make-up formulae, modifying the reproduction of the colors and the stability of the compositions, and then on the skin after application, which promotes cutaneous ageing (appearance of wrinkles, fine lines or yellowing of the skin). Mention may in particular be made, as coloring agents exhibiting this disadvantage, of the mixtures of brown-yellow iron oxides sold under the trade name “Sicomet Brown ZP 3569” by BASF, for example, pigments of organic origin, such as the pigment Orange 5 (CI 12075) or D & C Orange No. 5 (CI 45730:1) or D & C Orange No. 4 (CI 15510), and the aluminium lakes D & C Orange No. 5 Aluminium Lake, D & C Orange No. 4 Aluminium Lake or D & C Orange No. 10 Aluminium Lake.
Today, use is made of antioxidizing agents, such as, for example, ethoxyquin, in order to overcome this disadvantage. Unfortunately, it is often difficult to find an antioxidizing agent which is 100% effective due to the multiplicity of ingredients present in make-up compositions. Furthermore, antioxidizing agents themselves often generate, by oxidation, degradation products which can be a nuisance.
A subject-matter of the present invention is the use, in a cosmetic composition, in particular for obtaining an orange color, of a novel orange pigment with an intense and saturated color which is stable and which has the advantage of generating far fewer free radicals than the pigments conventionally used.
Surprisingly, the Applicant Company has found that some diketodiarylpyrrolopyrrole (abbreviated to DPP) derivatives make it possible to limit the production of free radicals, since they have the property of generating very few free radicals, and thus to avoid the use of antioxidants in the compositions. In addition, these pigments make it possible to obtain an intense and very vivid orange coloring which does not bleed on the skin and which is stable with regard to light, pH and temperature.
More specifically, a subject-matter of the invention is a colored cosmetic composition for topical application and more especially a cosmetic make-up composition comprising a pigment derived from diketodiarylpyrrolopyrrole of formula (I):
in which A and B are identical or different aryl radicals and DPP is a diketodiarylpyrrolopyrrolidyl radical, the diketodiarylpyrrolopyrrole derivative of formula (I) being substituted by 0 to 6 mol of —SO
3
M per mole of pyrrolopyrrole derivative, M being a hydrogen atom or a metal or ammonium cation.
When M is a metal cation, it is preferably a sodium, potassium or lithium cation.
The pyrrolopyrrole derivative of formula (I) is preferably substituted by 0 to 2 mol of —SO
3
M and more preferably by 0 to 0.75 mol of —SO
3
M per mole of pyrrolopyrrole derivative of formula (I).
Preferred pyrrolopyrrole derivatives do not comprise an —SO
3
M radical.
DPP is preferably a 1,4-diketo-3,6-diarylpyrrolo[3,4-c]pyrrolidyl radical of formula:
in which A
1
and A
2
are identical or different aryl radicals.
A, B, A
1
and A
2
can be aromatic or heteroaromatic radicals.
Particularly appropriate radicals are those of formulae:
in which:
R
1
and R
2
denote, independently of one another, a hydrogen or halogen atom or a C
1
-C
18
alkyl, C
1
-C
18
alkoxy, C
1
-C
18
alkylmercapto, C
1
-C
18
alkylamino, C
1
-C
18
alkoxycarbonyl, C
1
-C
18
alkylaminocarbonyl, —CN, —NO
2
, trifluoromethyl, C
5
-C
6
cycloalkyl, —CH═N—(C
1
-C
18
alkyl), phenyl,
imidazolyl, pyrazolyl, triazolyl, piperazinyl, pyrrolyl, oxazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, morpholinyl, piperidinyl or pyrrolidinyl radical, G denotes —CH
2
—, —CH(CH
3
)—, —C(CH
3
)
2
—, —CH═N—, —N═N—, —O—, —S—, —SO—, —SO
2
—, —CONH— or —NR
7
—,
R
3
and R
4
denote, independently of one another, a hydrogen or halogen atom or a C
1
-C
6
alkyl, C
1
-C
18
alkoxy or —CN radical,
R
5
and R
6
-denote, independently of one another, a hydrogen or halogen atom or a C
1
-C
6
alkyl radical, and R
7
is a hydrogen atom or a C
1
-C
6
alkyl radical.
In particular, A, B, A
1
and A
2
each denote a group of formula:
in which:
R
1
and R
2
each denote, independently of one another, a hydrogen, chlorine or bromine atom or a C
1
-C
4
alkyl, C
1
-C
6
alkoxy, C
1
-C
6
alkylamino, phenyl or —CN radical, G denotes —O—, —NR
7
—, —N═N— or —SO
2
—,
R
3
and R
4
denote hydrogen, and
R
7
is a hydrogen atom or a methyl or ethyl radical.
More particularly, A, B, A
1
and A
2
each denote a group of formula:
in which:
R
1
and R
2
each denote, independently of one another, a hydrogen, chlorine or bromine atom or a methyl, tert-butyl, phenyl or —CN radical.
At least one of the R
1
and R
2
radicals is preferably a hydrogen atom.
More preferably, at least one of the R
1
and R
2
radicals is a hydrogen atom and the other is in the 3- or 4- position of the phenyl nucleus.
Particularly preferred compounds are those in which A and B are identical and are chosen from the phenyl, 4-methylphenyl, 4-tert-butylphenyl, 4-chlorophenyl, 4-bromophenyl or biphenyl-1-yl (4-phenylphenyl) radicals, especially those in which A
1
and A
2
are also identical and are chosen from the phenyl, 4-methylphenyl, 4-tert-butylphenyl, 4-chlorophenyl, 4-bromophenyl and biphenyl-1-yl radicals.
A preferred class of pyrrolopyrrole derivatives is that in which A
1
and A
2
each denote a 4-tert-butylphenyl radical, especially that in which A and B are identical and are chosen from the phenyl, 4-tert-butylphenyl and 4-methylphenyl radicals, preferably the 4-tert-butylphenyl radical.
Thus, a preferred compound according to the invention is the pyrrolopyrrole derivative in which A, B, A
1
and A
2
each denote a 4-tert-butylphenyl radical.
Another preferred class of pyrrolopyrrole derivatives is that in which A
1
and A
2
each denote a 4-methylphenyl radical and A and B are identical and are chosen from the phenyl, 4-tert-butylphenyl and 4-methylphenyl radicals, preferably the 4-tert-butylphenyl radical.
The preparation of the diketodiarylpyrrolopyrroles of formula (I) is disclosed in particular in U.S. Pat. No. 5,786,487.
Use is preferably made of the 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole derivatives exhibiting the following formula (II):
in which R and R
1
have the meanings indicated below.
R
R
1
H
H
H
Cl
H
CH
3
H
tert-butyl
Dees Jose' G.
L'Oreal
Lamm Marina
Nixon & Vanderhye P.C.
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