Fluorous anhydrous composition and cosmetic product for makeup containing the same

The present invention relates to a homogeneous anhydrous composition containing at least one fluorine-containing wax having a carbon-containing skeleton structure and at least one fluorine-containing oil in combination. The present invention also relates to make-up products or care products containing such anhydrous compositions.

The use of fluorinated oils in the formulation of cosmetic compositions is particularly desired as such oils provide excellent film forming properties and water resistance as well as sebum resistance. However, such compositions are difficult to achieve because the fluorinated oil is essentially incompatible with many polar and non-polar hydrocarbon compounds. Homogeneous combinations of fluorinated oils and waxes have already been carried out by using surfactants, but so far, fluorinated oil-based compositions, especially anhydrous compositions, in the absence of surfactants. It was impossible to get things.

<p> As a result of diligent research on various types of compounds, in an unexpected and surprising manner, by combining several fluorinated oils with a fluorinated wax having at least one carbon-containing skeletal structure, it is completely completed. It has been found that a homogeneous anhydrous mixture can be produced.</p><p> It was also confirmed that this special combination can advantageously construct the fat phase of various compositions for make-up and care cosmetics, which presents a particularly good texture and gives the skin excellent flexibility and pleasant feel after application. Was done.</p>

<p> Therefore, the present invention aims for a homogeneous anhydrous composition or phase containing at least one fluorinated wax having a carbon-containing skeleton structure and at least one fluorinated oil, which is optionally interrupted by one oxygen atom. It is said.</p>

The expression "fluorine-containing wax having a carbon-containing skeleton structure" has a melting point of about 30 ° C or higher and contains more fluorine atoms than the number of hydrogen atoms, and this carbon-containing skeleton structure has at least one oxygen atom. Means a compound that is solid at room temperature and can be interrupted by. This wax contains only fluorine, hydrogen and carbon, and in some cases oxygen atoms. Oil is a drainage compound that is liquid at room temperature (25 ° C).

Examples of the fluorine-containing oil compatible with the fluorine-containing wax having a carbon-containing skeleton structure include a perfluorinated compound, a fluorosilicone, a fluoroalkyl and a heterofluoroalkyl compound. In the present invention, a perfluorinated compound is a compound in which all hydrogen atoms thereof are replaced by fluorine atoms.

A-Perfluoropolyesters satisfying this definition include the following, in particular: 1) Perfluoropolyesters satisfying the following formulas (I) and (II).<chemistry num="1"><img file="JP2005290014A_D0001.tif" /></chemistry>(In the above equation, n is 7 to 30), and<chemistry num="2"><img file="JP2005290014A_D0002.tif" /></chemistry>(In the above formula, the m / m'ratio is 20-40 and the molecular weight is 500-20000):

These perfluoropolyesters of formulas (I) and (II) are sold by DUPONT under the name "FLUORTRESS LM36®", respectively, and, for example, 10^-7Examples include those sold under the generic name "FOMBLIN" by MONTEFLUOS, such as the mmHg vapor pressure FOMBLIN HCR®.

2) Perfluorocycloalkyl of the following formula (III):<chemistry num="3"><img file="JP2005290014A_D0003.tif" /></chemistry>(In the above equation, e is equal to 4 or 5, g is equal to 1 or 2, p is equal to 1, 2 or 3. Where g = 2, the atomic groups are not necessarily alpha to each other. is not it)

Compounds of formula (III) include, in particular, perfluoromethylcyclopentane sold by BNFL FLUOROCHEMICALS under the names "FLUTEC PC1®" and "FLUTEC PC3®" with a vapor pressure of 368 mbar, respectively. Perfluorodimethylcyclohexane can be mentioned. 3) Perfluorophenanthrene sold under the name of "FLUTEC PC11 (registered trademark)" of BNFL FLUORO CHEMICALS.

Examples of the B-fluorinated silicone include fluorosilicone compounds satisfying the following formula (IV):<chemistry num="4"><img file="JP2005290014A_D0004.tif" /></chemistry>(In the above equation, k is 1 to 17; l is 1 to 18; p is 1 to 6; R1 is a hydrogen atom or C.₁~ C₆Represents an alkyl group of; R₂Is C₁~ C₆Alkyl group or group-OSi (R)₃)₃; And R₃Is C₁~ C₄Represents an alkyl group of)

Specific examples of compounds satisfying formula (IV) include: N- (-2-F-octyl-ethyloxycarbonyl) -3-aminopropylbis (trimethylsiloxy) methylsilane, N- (-(- 2-F-hexyl-ethyloxycarbonyl) -3-aminopropylbis (trimethylsiloxy) methylsilane, N- (-2-F-butyl-ethyloxycarbonyl) -3-aminopropylbis (trimethylsiloxy) methylsilane, N- (-2-F-octyl-ethyloxycarbonyl) -3-aminopropyltris (trimethylsiloxy) silane, N- (-2-F-hexyl-ethyloxycarbonyl) -3-aminopropyltris (trimethylsiloxy) silane, And N- (-2-F-butyl-ethyloxycarbonyl) -3-aminopropyltris (trimethylsiloxy) silane.

Examples of the C-fluoroalkyl or heterofluoroalkyl compound include those satisfying the following formula (V): CH.₃-(CH₂) h- [Z] t- (CF₂) i-CF₃ (V) (In the above equation, t is equal to 0 or 1, h is equal to 0,1,2 or 3, i is equal to 2,3,4 or 5, and Z is O, S, or NR4. , R₄Is hydrogen, group-(CH₂) h-CH₃Or-(CF₂) i-CF₃Represents.

Compounds of formula (V) include, in particular, methoxynonafluorobutane (t = 1, Z = O, n = 0 and m = 3) or methoxynonafluorobutane sold by 3M under the name "MSX4518®". Ethoxynononafluorobutane (t = 1, Z = O, n = 1 and m = 3) sold by Archimex under the name "HFE7200" can be mentioned.

The oil of the present invention has a boiling point of less than 220 ° C, preferably less than 120 ° C. Examples of the fluorine-containing wax having a carbon-containing skeleton structure as defined above capable of forming a homogeneous anhydrous composition with the fluorine-containing oil include a fluorine-containing ester satisfying the following formula (VI). it can:<chemistry num="5"><img file="JP2005290014A_D0005.tif" /></chemistry>(In the above formula, R₄Is a hydrogen atom or<chemistry num="6"><img file="JP2005290014A_D0006.tif" /></chemistry>A represents a linear or branched alkylene or alkenylene chain containing a hydroxyl group in C1 to C18; c is 1 to 17 and d is 1 to 18).

As a compound of formula (VI), in particular<chemistry num="7"><img file="JP2005290014A_D0007.tif" /></chemistry>2F-octyl-ethyl dodecane 1,12, geoart, and C₁-C₆Perfluoroalkyl tri-citrate, more specifically, perfluorobutyl tri-citrate sold by DUPONT under the name "ZONYL TBC®".

Other fluorine-containing waxes that can be used in the present invention include polytetrafluoroethylene (PTFE) wax. A wax having a boiling point of 45 ° C to 150 ° C, particularly such as the fluorine-containing ester of formula (VI), is utilized.

In the anhydrous composition according to the present invention, the fluorine-containing oil is generally present in a proportion of 20 to 95% by weight, preferably 60 to 80% by weight, based on the total weight of the composition. The fluorine-containing wax having a carbon-containing skeleton structure is generally present in a proportion of 5 to 80% by weight, preferably 20 to 40% by weight, based on the total weight of the composition.

In one particular embodiment, the anhydrous composition described above further comprises one or more other fatty substances, which may be selected from oils, gums and / or so-called pasty fatty substances. be able to.

The oils of the anhydrous composition may be mineral, animal, vegetable or synthetic, which may or may not be volatile at room temperature. Examples of the mineral oil include paraffin oil. Examples of animal oils include squalene and perhydrosqualene. Vegetable oils include, among others, sweet tongue oil, calophyllum oil, palm oil, avocado oil, jojoba oil, sesame oil, olive oil, castor oil, and grain germ oil such as wheat germ oil.

Synthetic oils include, among others: (1) R₅-COOR₆Ester of the formula: Where R₅Is C₇-C₂₀Represents a higher fatty acid residue in R₆Is C₃-C₃₀Represents the hydrocarbon group of.

These esters include, in particular, Purcellin oil, butyl myristate, isopropyl myristate, cetyl myristate, isopropyl palmitate, butyl stearate, hexadecyl stearate, isopropyl stearate, octyl stearate, isocetyl stearate, Examples include decyl oleate, hexyl laurate, isononyl isononanoate, and esters derived from lanophosphate such as isopropyl lanophosphate and isocetyl lanophosphate.

Other synthetic oils include isododecane, isohexadecane, polyisobutene and hydrogenated polyisobutene, as well as octanoic acid esters and decanoic acid esters of polyalcohols such as glycols and glycerol, and alcohols such as acetylglycerides, cetyl ricinoleate or Examples thereof include ricinoleic acid ester of polyalcohol, propylene glycol dicaprylate and diisopropyl adipate.

(2) Fat alcohols such as oleic acid alcohol, linoleic acid alcohol, linolenic acid alcohol, isostearyl alcohol and octyldodecanol;

(3) Possibly functionalized linear polydiorganosiloxanes, cyclic polydiorganosiloxanes, especially cyclotetra and pentadimethicone and organopolysiloxanes such as alkyl, alkoxy or phenyldimethicone, and especially phenyltrimethicone. Silicone oil; the oil can make up 0-50%, more preferably 0-20% by weight, of the total weight of the composition.

b- Waxes of anhydrous compositions other than fluorine-containing waxes may be derived from minerals, fossils, animals, plants, synthetic waxes, hydrogenated oils or fatty acid esters coagulated at 25 ° C. There may be. Examples of the mineral wax include microcrystalline wax, paraffin, petrolatum and selecin. Examples of fossil wax include Ozokerite wax and Montan wax.

Examples of animal wax include beeswax, whale wax, lanolin wax, and lanolin-derived derivatives such as lanolin alcohol, hydrogenated lanolin, lanolin hydroxide, acetylated lanolin, lanolin fatty acid, and acetylated lanolin alcohol.

Examples of the vegetable wax include candelilla wax, carnauba wax, wood wax and cacao butter. As a synthetic wax, especially CH₂= CH-R₇Examples thereof include a copolymer of ethylene and a monomer satisfying the above formula and an ethylene homopolymer. In this formula, R₇Is C₁-C₃₀Represents the allyl or aralkyl group of₇Is preferably a methyl, ethyl, propyl, isopropyl, butyl, decyl, dodecyl or octadecyl group.

Similarly, waxes obtained by the Fischer-Tropsch synthesis method as well as silicone waxes can also be used. Examples of the hydrogenated oil that solidifies at 25 ° C include hardened castor oil, hardened palm nut oil, hardened tallow and hardened coconut oil.

Examples of the fatty acid ester coagulated at 25 ° C include propylene glycol monomyristate and myristyl myristate. Further waxes available in compositions according to the invention include cetyl alcohols, steryl alcohols, monocoagulated at 25 ° C, di and triglycerides, monoethanolamide stearic acid, rosin and derivatives thereof such as abietic acid. Glyceric acid and glycerol, scroglycerides and oleic acid, myristic acid, lanophosphate, stearic acid and calcium dihydroxystearate, magnesium, zinc and aluminum can be mentioned. Preferably, a wax having a melting point of 45 ° C to 150 ° C is used. This wax in particular makes up 0-20% of the total weight of the composition.

The C-paste type fatty substance may be mineral, animal, vegetable or synthetic. Examples of the paste-like fatty substance include synthetic esters such as arachidyl propionate and vinyl polylaurate, polyethylene wax, and organopolysiloxanes, such as alkyl dimethicone, alkoxydimethicone or dimethicone ester.

The present invention also aims at make-up cosmetics or care cosmetics or compositions containing the above-mentioned homogeneous anhydrous composition or phase.

According to a particular first embodiment, the makeup cosmetic or care product is anhydrous and contains a homogeneous anhydrous composition in proportions ranging from about 0.5 to 100% by weight based on the total weight of the product. To do.

The anhydrous product can take the form of a stick, such as a lipstick or cover foundation, or the form of an anhydrous compact, such as a foundation, eyeshadow, brush or mascara.

If the anhydrous product is in the form of a stick or compact, it can contain pigments and fillers in the form of fine particles with an average particle size of 0.02 to 50 μm. The pigment may be mineral or organic, and may be in the form of a metal lake. These pigments include titanium dioxide, zinc oxide, D &amp; C Red No. 36 and D &amp; C Orange No. 17, D &amp; C Red No. 7, 11, 31, and 34 calcium lake, D &amp; C Red No. 12 barium lake, and D &amp; C Red No. 13. No. Strontium Lake, FD &amp; C Yellow No. 5, FD &amp; C Yellow No. 6, D &amp; C Red No. 27, D &amp; C Red No. 21, FD &amp; C Blue No. 1 Aluminum Lake, Iron Oxide, Manganese Purple, Chromium Oxide and Ultramarine.

The filler may be natural or synthetic. Fillers include: i) talc, kaolin, mica, silica, silicate, alumina, zeolite, hydroxyapatite, silk mica, mica titanium, barium sulfate, bismuth oxychloride, boron nitride, And powder metal powders such as aluminum; ii) vegetable powders such as starch powder, corn flour, soft wheat flour and rice flour; iii) organic powders such as nylon, polyamide, polyester, polytetrafluoroethylene or polyethylene powder.

These different powders may be further coated with, for example, fatty acid metal salts, amino acids, lecithin, collagen, silicone-containing compounds, fluorine-containing compounds, or any other conventional coating.

In addition to the pigments described above, at least one colorant may be present, and such colorants include erotic derivatives such as D &amp; C Red No. 21, D &amp; C Red No. 27, and D &amp; C Red No. 21. Halogenated fluorosane derivatives such as the combined D &amp; C Orange No. 5 and D &amp; C Orange No. 10 can be mentioned.

In make-up cosmetics or care cosmetics, the proportion of pigments and / or colorants is generally between about 0.1-25% by weight, more preferably between 0.1 and 15% by weight, based on the total weight of these products. .. Fillers are generally present in make-up or care cosmetics in a proportion of up to about 98% by weight to the total weight of these products.

Anhydrous products such as those described above can, of course, further contain one or more conventional cosmetic or dermatological additives or adjuvants.

In the second embodiment, the make-up cosmetic or care cosmetic is essentially (i) the homogeneous anhydrous composition or phase described above in a proportion of about 0.1-50% by weight to the total weight of the composition, (. ii) Consists of at least one emulsifier at a ratio of about 4 to 97% by weight based on the total weight of the composition and (iii) about 0.5 to 10% by weight based on the total weight of the dispersion. It is a dispersion in the form of a stable emulsion of water-in-oil type (W / O) or oil-in-water type (O / W).

Emulsifiers or surfactants that can be used in compositions in the form of W / O or O / W emulsions include, among other things, silicone-containing surfactants, especially those belonging to the copolyol dimethicone and copolypolymer alkyl or alkoxydimethicone groups. Surfactants can be mentioned. Examples of these latter ones include compounds that satisfy the following general formulas:<chemistry num="8"><img file="JP2005290014A_D0008.tif" /></chemistry>(In the above formula, R₈Is a hydrogen atom, C₁-C₁₆Alkoxy, alkoxy or acyl, R₉Is C₈-C₄₅Alkoxy or alkoxy group of, u = 0 ~ 200, v = 1 ~ 40, w = 0 ~ 100, group -O- (C₂H₄O) x-(C₃H₆O) yR₈The molecular weight of is 250 to 2000, and x and y are selected so that the weight ratio of oxyethylene / oxypropylene is between 100: 0 and 20:80. )

Commercially available products that may contain all or part of the copolyol alkyl dimethicone include, in particular, "ABIL WE09®", "ABIL EM90®", or "ABIL WS08®" by GOLD SCHMIDT. Commercially available under the name "Q2 5200 (registered trademark)" or "Q2 3225C (registered trademark)" by DOW CORNING, and "218 | 138 (registered)" by GENERAL ELECTRIC. It can be mentioned that it is commercially available under the name of "trademark)".

Surfactants can also be selected from anionic or nonionic surfactants. In this regard, refer to the reference "Encyclopedia of Chemical Technology KIRK-OTHMER" (Vol. 22, pp. 333-432, 3rd edition, 1979 WILEY) for the definition of the physical properties and function (emulsification) of surfactants. For anionic and nonionic surfactants, see pages 347-377 of this document.

These two groups of surfactants preferably utilized in the compositions according to the invention are: Among the nonionic surfactants: fatty acids, fatty alcohols, polyethoxyls or polyglycerols. Fatty alcohols containing, such as polyethoxyl-containing stearyl alcohols, fatty acid esters and saccharose esters, alkyl glycosyl esters, especially alkyls containing polyoxyethylene (C).₁-C₆) Fatty acid esters of glucose; and amine stearate among anionic surfactants.

These dispersions are preferably creamy and can be used as make-up cosmetics or care cosmetics.

The above-mentioned products or compositions, whether anhydrous or dispersed, have excellent cosmetic textures, as well as excellent cosmetic durability against friction, water or sebum. Shows the characteristics.

These products or compositions as described above may further include vitamins, hormones, antioxidants, preservatives, fragrances, thickeners, water replenishers, wetting agents, anions, nonionic or amphoteric polymers, cosmetics or dermatology. It can contain one or more conventional cosmetic adjuvants such as the above active ingredients.

The present invention is illustrated by the following examples of quantities expressed by weight.<u style="single">Examples of cosmetic compositions</u><u style="single">Example 1</u>: Lipstick According to the present invention, lipstick was prepared by mixing the following components. Polyperfluoroisopropyl ether 5g 2F-octyl-ethyl dodecane 1,12 Geoart 40g perfluorodecalin 35g 3M marketed under the name "FLUORTRESS LM36®" by DUPONT. Methoxynononafluorobutane 10g pigment 10g commercially available at

<u style="single">Example 2</u>: Stick Foundation A foundation was prepared by mixing the following ingredients according to the present invention: 2F-octyl-ethyl dodecane 1,12 Geoart 30g N- (-2-F-octyl-ethyloxycarbonyl) -3-amino Propyl-bis (trimethylsiloxy) methylsilane 60g pigment 10g

<u style="single">Example 3</u>: Care cream An oil-in-water emulsion was prepared with the following ingredients according to the conventional emulsion manufacturing method. FLUORTRESS LM36 (1) 10g ZONYL TBC (2) 8g Trifluoromethyl C₁-₄Alkyl Dimethicone (Shinetsu) 12g ABIL WE09 (3) 5g Salt 0.7g Amount that makes 100g of water in total (1) Polyperfluoroisopropyl ether (Dupont de Nemours) (2) tri-Perfluoroalkylethyl citrate (same as above) (3) ) Polyglyceryl-4-isosteertert / cetyldimethicone copoly polyol / hexyl laurate (Goldschmidt)