WO2002042380A1

WO2002042380A1 - Use of pigments in cosmetic, in particular in make-up

Info

Publication number: WO2002042380A1
Application number: PCT/IB2001/001784
Authority: WO
Inventors: Bansi Lal Kaul; Bruno Piastra
Original assignee: Clariant International Ltd; Clariant Finance BVI Ltd
Current assignee: Clariant International Ltd; Clariant Finance BVI Ltd
Priority date: 2000-11-24
Filing date: 2001-09-27
Publication date: 2002-05-30
Anticipated expiration: 2003-05-24
Also published as: AU2001287995A1; WO2002042380A8

Abstract

The invention relates to the use as a pigment in cosmetic compositions of compounds corresponding to formula (I) or (II) in which the substituents are as defined in Claim 1, to cosmetic compositions contai-ning at least one pigment as defined, and also to processes for making up the skin, for coloring the nails or for dyeing keratin fibers by applying such a composition.

Description

USE OF PIGMENTS IN COSMETIC, IN PARTICULAR IN MAKE-UP

The present invention relates to the use of pigments in cosmetics, to cosmetic compositions containing them and to cosmetic treatment processes using them.

Research is under way in the cosmetics field, and in particular for make-up compositions such as foundations, tinted creams, mascaras, face powders, eye shadows, lipsticks and nail varnishes, for pigments capable of giving these various types of products a wide range of colorations that are reproducible over time, and insoluble in most cosmetic media used, such as water and cosmetically acceptable solvents. These pigments must moreover be stable at the pHs usually used or encountered in cosmetics.

The Applicant has just discovered pigments that are particularly advantageous to use in cosmetics, and in particular for use in make-up compositions, especially foundations, tinted creams, mascaras, face powders, eye shadows, lipsticks, nail varnishes and temporary hair dyes. These pigments produce a very wide range of reproducible colorations, which is highly desirable in the cosmetics field, ranging from yellow to brown and passing through orange-yellow, orange and bright red. They are also stable at pHs of between 6 and 8 and insoluble in most cosmetic m^dia.

In addition, the high crystallinity of these pigments prevents the phenomenon of releasing the colors in the formulations.

One subject of the invention is the use of compounds of formulae (I) and (II)

in which Ri and R₂ denote, independently of each other, the atoms required to form a substituted or unsubstituted aromatic ring or an aliphatic ring or a heterocycle,

R₃ and R₄ independently of each other, denote a hydrogen atom, a substituted or unsubstituted phenyl radical, a branched or unbranched, saturated or unsaturated alkyl radical or a carbamate group (III)

in which

R₅ denotes a substituted or unsubstituted phenyl radical or a branched or unbranched saturated or unsaturated alkyl radical

in which the nuclei denoted by A and B, independently of each other, include aromatic rings linearly substituted on positions 2, 3 and 9, 10, or angularly substituted on positions 1 , 2 and 8, 9 or on 3, 4 and 10, 11 with heterocyclic groups allowing the formation of the following species (1) to (3)

in which R₃ and R₄ independently of each other, denote, as in formula (I), a hydrogen atom, a substituted or unsubstituted phenyl radical, a branched or unbranched saturated or unsaturated alkyl radical, or a carbamate group (III)

-R. (Ill)

O^'

in which

R₅ denotes a substituted or unsubstituted phenyl radical or a branched or unbranched, saturated or unsaturated alkyl radical,

as a pigment in cosmetic compositions for treating and/or coloring keratin materials such as the skin, the nails and the hair. Given their insoluble nature, these pigments are used more particularly in foundation, tinted cream, mascara, face powder, eye shadow, lipstick and nail varnish compositions and temporary hair dyeing compositions. They may be used alone or mixed with other conventional mineral or organic pigments.

The pigments of formula (I) and the process for preparing them are described in publication WO 98/32800. The pigments of formula (II) and the process for preparing them are described in publication EP 0 889 046 A1.

In formula (I), R_T and R₂ are, independently of each other, preferably chosen from the following groups

(a) (b) (c) (d) (e)

in which

Hal denotes a halogen atom of Cl, F, Br or I type R denotes a C C₄ alkyl radical, preferably methyl or ethyl a has the value 1 , 2, 3 or 4 b has the value 1 , 2, 3 or 4

The compounds of formula (II) that are particularly preferred are chosen from the derivatives of benzimidazolone-triphenodioxazine type corresponding to formula (IV) below:

in which R₃ denotes a substituted or unsubstituted phenyl radical and R₄ denotes a hydrogen atom.

The cosmetic compositions which constitute another subject of the invention are characterized in that they contain at least one compound corresponding to formula (I) or (II) defined above, in a cosmetically acceptable medium.

The pigments of formulae (I) and (II) are generally used at a concentration which can range between 0.1% and 80% by weight and preferably between 1 % and 30% by weight relative to the total weight of the composition. The cosmetically acceptable medium is a medium that is essentially a non-solvent for the pigment.

The expression "essentially non-solvent medium" means a medium that dissolves less than 1% of the said pigment.

The compositions may be in the form of a lotion, a thickened lotion, a gel, emulsions (creams, milks or ointments), vesicular dispersions, a powder or a stick. They may optionally be packaged as an aerosol and may be in the form of a mousse or spray.

The compositions are preferably emulsions of oil-in-water or water-in-oil type or liposo- mal dispersions or alternatively solid preparations.

When they are used in the form of emulsions, they may also contain surfactants that are well known in the prior art, such as anionic, nonionic, cationic or amphoteric surfactants or mixtures thereof.

These compositions may also contain fatty substances, organic solvents, silicones, thickeners, softeners, sun screens, free-radical scavengers, antifoams, moisturizers, fragrances, preserving agents, antioxidants, fillers, sequestering agents, treating agents such as nonionic, cationic, anionic or amphoteric polymers or mixtures thereof, propellants and acidifying or basifying agents.

The fatty substances may consist of an oil or a wax or mixtures thereof, fatty acids, fatty alcohols, fatty acid esters, petroleum jelly, paraffin, lanolin, hydrogenated lanolin or acetylated lanolin.

The oils are chosen from animal oils, plant oils, mineral oils, synthetic oils and in particular hydrogenated palm oil, hydrogenated castor oil, liquid petroleum jelly, liquid paraffin, purcellin oil and silicone oils.

The waxes are chosen from animal waxes, fossil waxes, plants waxes, mineral waxes and synthetic waxes. Mention may be made more particularly of bees waxes, carnauba wax, candelilla wax, sugar cane wax, Japan wax, ozokerites, montan wax, microcry- stalline waxes and paraffins. When the compositions are used for coloring the nails, they are in the form of "nail varnish" products containing the pigment in accordance with the invention dispersed in a cosmetically acceptable solvent containing one or more resins and ingredients usually used in products of this type.

When the compositions are used for coloring the hair, they preferably comprise a medium which is suitable for temporary dyeing, consisting of water, a solvent or a mixture of water and one or more cosmetically acceptable solvent(s), containing at least one pigment in accordance with the invention, in dispersed form.

The solvents are chosen more particularly from C C₆ lower alcohols, alkylene glycols, for instance ethylene glycol or propylene glycol, glycol ethers, for instance ethylene glycol monomethyl ether, monoethyl ether or monobutyl ether, ethylene glycol mono- ethyl ether acetate, propylene glycol monomethyl ether and dipropylene glycol mono- methyl ether, and methyl lactate.

The solvents that are particularly preferred are ethyl alcohol and propylene glycol.

The compositions in accordance with the invention may also contain, in addition to the pigment defined above, other pigments generally used in cosmetics, in particular white or colored pigments, nacreous and/or purlescent pigments for varying the colorations or for increasing the protection against ultraviolet radiation. Among these pigments which may be used are nanopigments of metal oxides, such as titanium oxide, zinc oxide, cerium oxide and/or zirconium oxide with a mean diameter of less than 100 nm and preferably between 1 and 50 nm. These pigments may be coated.

Another subject of the invention consists of a process for coloring or making up keratin materials such as the skin, the nails, the eyelashes, the eyebrows and the hair, using a composition containing, in a cosmetically acceptable medium, at least one pigment corresponding to formula (I) or (II) as defined above.

The examples which follow are intended to illustrate the invention without, however, having a limiting nature. FORMULATION EXAMPLES

Face powder: Talc (qs) 100.00 g

Polyethylene powder 5.00 g Magnesium carbonate 1 1.00 g Isopropyl myristate 1.50 g Liquid petroleum jelly 1.50 g Sorbitol 0.50 g Compound of formula (1) 0.25 g

Insoluble pigment consisting of a dye from the 0.65 g indigo family deposited on a filler, known as DC Red 30 LAKE in the CTFA dictionary Ultramarine blue 0.15 g Titanium mica 5.00 g

Lipstick:

Castor oil (qs) 100.00 g

Butyl Hydroxy Toluene (BHT) 0.15 g

Liquid lanolin 15.00 g

Microcrystalline wax 15.00 g - Sesame oil 11.00 g

1-[[4-(phenylazo)phenyl]azo]-2-naphthol, known as 1.00 g

DC Red No. 17 in the CTFA dictionary

Compound of formula (2) 1 -00 g

Titanium mica 5.00 g

Octyl glyceryl behenate 15.00 g

Fragrance (qs)

Nail varnish:

Toluene (qs) 100.00 g

Nitrocellulose 10.90 g - Toluene sulphonamide formaldehyde resin 9.85 g

Acetyl tributyl citrate 6.50 g

Butyl acetate 21.80 g

Ethyl acetate 9.40 g

Stearylkonium hectorite 1.36 g - Citric acid 0.06 g

Ultramarine blue 0.01 g

Titanium dioxide 0.77 g

Calcium salt of 3-hydroxy-4-[(1-sulpho-2-naphthylazo]- 0.07 g

2-naphthalene carboxylic acid known as DC Red 34 in the CTFA dictionary

Compound of formula (3) 0.50 g

Titanium mica 0.60 g Isopropyl alcohol 7.80 g

Claims

1. Use as a pigment in cosmetic compositions of a compound corresponding to formula (I) or (II)

in which

Ri and R₂ denote, independently of each other, the atoms required to form a substituted or unsubstituted aromatic ring or an aliphatic ring or a heterocycle, R₃ and R independently of each other, denote a hydrogen atom, a substituted or unsubstituted phenyl radical, a branched or unbranched, saturated or unsaturated alkyl radical or a carbamate group (III)

in which

in which

R₃ and R₄ independently of each other, denote, as in formula (I), a hydrogen atom, a substituted or unsubstituted phenyl radical, a branched or un- branched saturated or unsaturated alkyl radical, or a carbamate group (III)

O

in which

R₅ denotes a substituted or unsubstituted phenyl radical or a branched or un- branched, saturated or unsaturated alkyl radical.

Use according to Claim 1 , characterized in that the cosmetic compositions consist of foundation, tinted cream, mascara, face powder, eye shadow, lipstick or nail varnish compositions and temporary hair dyeing compositions.

Cosmetic composition for the cosmetic treatment or coloring of keratin materials, characterized in that it contains, in a cosmetically acceptable medium, at least one pigment consisting of the compound corresponding to formula (I) or (II)

in which the substituents are as defined in Claim 1.

Composition according to Claim 3, characterized in that the pigment of formula (I) or (II) is present in a concentration of between 0.1 % and 80% and preferably between 1 % and 30% by weight relative to the total weight of the composition.

Composition according to either of Claims 3 and 4, characterized in that the composition is in the form of a lotion, a thickened lotion, a gel, an emulsion, a vesicular dispersion, a powder or a stick or is optionally packaged as an aerosol in the form of a spray or mousse.

Composition according to any one of Claims 3 to 5, characterized in that it contains fatty substances, organic solvents, silicones, thickeners, softeners, surfactants, sun screens, free-radical scavengers, antifoams, moisturizers, fragrances, preserving agents, antioxidants, fillers, sequestering agents, treating agents, propellants, acidifying or basifying agents, or other pigments.

Composition according to Claim 3, characterized in that it is to be used for coloring the nails and that it is in the form of a dispersion of the pigment in a cosmetically acceptable solvent containing one or more resins.

8. Composition according to Claim 3, characterized in that it is to be used for the temporary dyeing of the hair and in that it is in the form of a dispersion of the pigment in a medium which is suitable for dyeing.

9. Process for making up the skin, the eyelashes or the eyebrows, characterized in that at least one composition as defined in any one of Claims 3 to 8 and containing as pigment at least one pigment of formula (I) or (II) as defined in Claim 1 or 3 is applied to the skin, the eyelashes or the eyebrows.

10. Process for coloring the nails, characterized in that at least one composition containing a cosmetically acceptable solvent, one or more resins and at least one pigment consisting of the compound of formula (I) or (II) as defined in Claim 1 or 3 is applied to the nails.

11. Process for dyeing keratin fibers, in particular the hair, characterized in that at least one composition containing, in a medium which is suitable for dyeing, at least one pigment consisting of the compound of formula (I) or (II) as defined in Claim 1 or 3 is applied to the fibers.