FR2773065A1 - Use of volatile polyfluorinated organic solvent in cosmetics - Google Patents

Abstract

A volatile polyfluorinated organic solvent with a vapour pressure above 2000 Pa at 25 deg C is used as an anti-transfer agent in a cosmetic make-up or sunscreen composition containing pigment and/or filler particles. An Independent claim is also included for the preparation of the cosmetic composition or sunscreen.

Description

- I - The present invention relates to the use of a certain

  class of volatile fluorinated compounds in cosmetic make-up or sun protection compositions in order to avoid

  the so-called "transfer" phenomena.

  By "transfer" is meant in this type of cosmetic composition, the displacement of a fraction of the composition by

  contact with another medium, whether of the same nature or of

  different ture. Thus, when these are intended for the ma-

  skittles such as eyeshadows, eyeliners, or mascaras, they can be transferred to the hands by friction

  or by contact of these with the eyes. When these composi-

  are lipsticks, these can be transferred

  on the teeth, hands or on the cheeks of another person

  rings. Whatever the type of these compositions, they can also by transfer, stain the napkins and leave imprints on the glasses, cups and other containers. In addition, when the compositions are foundations, a transfer can also occur from the foundation.

  on the collar of the blouses and so stain them.

  In addition to this transfer problem, the compositions of

  makeup may also exhibit migra-

  tion, that is to say that the compositions tend to propagate inside the fine lines and / or wrinkles of the skin, in particular in the case of foundations, in the fine lines around the lips in the case lipsticks and, in the creases of the eyelids

  in the case of eyeshadows.

  These transfer and migration phenomena are particularly

  severely damaging to the extent that they have an effect

  unsightly and a number of disadvantages such as men-

mentioned above.

  In order to remedy this, it has already been proposed, in particular

  in US Patent 5,505,937 to use volatile oils in particular

  cyclic silicones as well as hydrocarbon products

  such as Ce-C isoparaffins, combined with a silicone resin

-2-

cone and waxes.

  If this type of makeup composition makes it possible to avoid transfer phenomena, it nevertheless results in the formation

  on the skin with a dry film, consisting of waxes and as pigments

  matt pect, linked to a heterogeneous film surface condition. It has also been proposed to produce make-up products without transfer, using aqueous dispersions of hydrophobic or "latex" polymers which, by drying on the skin, make it possible to obtain a dry film which may have a certain

shine.

  However, the drawback of these aqueous dispersions of hydrophobic polymers is linked to discomfort and difficulty in applying to the skin, in particular to the lips in the case of lipsticks. It is indeed necessary with this type of composition, to have to wait for the aqueous phase to evaporate, this

  which may take several minutes.

  After numerous studies on various types of compounds, it has been found, surprisingly and unexpectedly, that by using a certain class of volatile fluorinated solvents it is possible

  to remedy, in a particularly satisfactory and effective manner

  cace, to the disadvantages raised by the problems of transfer and

migration.

  In addition, the use of volatile fluorinated solvents

  provides particularly quick drying after application

  tion of the composition on the skin, which is not the case with the compositions of the prior art, based on cyclic silicones or

of hydrocarbon compounds.

  Another particularly significant advantage is

  being able to obtain the compositions in complete safety, while

  sure o volatile fluorinated solvents do not have a flash point, which makes it possible to produce the compositions at high temperature, and therefore has a definite advantage when using substances having a melting point higher than room temperature.

  Finally, the use of easily volatile fluorinated solvents

  lite the incorporation in compositions of high concentrations

  -3 - derived from non-volatile fluorinated derivatives, these being completely

  miscible with volatile fluorinated solvents. We can thus obtain

  finish a highly fluorinated, shiny or satin residual film, and re-

resistant to water and fatty substances.

  The present invention therefore relates to the use

  in a cosmetic makeup or protective composition

  laire, containing pigment and / or filler particles, of at least one volatile fluorinated solvent as anti-transfer agent, said fluorinated solvent having a vapor pressure greater than 20 mba (2000 Pa) at 25 C and preferably greater than 40 mba

(4000 Pa).

  Among the volatile fluorinated solvents which can be used according to the invention and which meet the vapor pressure criterion mentioned above, there may be mentioned in particular: 1) the perfluorocycloalkyl compounds corresponding to the following formula (I): (CF2) n (CF- (CF2 ) pF) m (I) in which: nest 4 or 5, m is 1 or 2, and p is 1, 2 or 3

  provided that when m = 2, the groupings are not necessary

  usually in alpha, relative to each other, and 2) the fluorinated alkyl ethers corresponding to the following formula (II): CH3- (CH2) nO- (CF2) m-CF3 (II) in which: n is 0, 1, 2 or 3, and

m is 2, 3, 4 or 5.

  Among the perfluorocycloalkyls of formula (I), one can

  in particular, cite perfluoromethylcyclopentane and perfluorome-

  thylcyclohexane, sold respectively under the names of "FLUTEC PC1" and "FLUTEC PC3" by BNFL FLUOROCHEMICALS Ltd. -4-

  Among the fluorinated alkyl ethers of formula (II) there may be mentioned

  strongly cite the nanofluoromethoxybutane sold under the name

  tion of "MSX 4518 (R" by the company 3M.

  In make-up compositions or so-called product

  z laire, the proportion of volatile fluorinated solvent is generally between 2 and 98% by weight, but preferably between 5 and

  % by weight relative to the total weight of the composition.

  Pigments in makeup or product compositions

  solar as well as the charges, are in the form of parti-

  very fine cells with an average particle size included

between about 0.02 to 50 pm.

  The pigments of the compositions can be mineral or organic or else in the form of metallic lakes. Among these pigments, mention may be made of titanium dioxide, zinc oxide, D&C Red No. 36 and D&C Orange No. 17, calcium lakes of D&C Red No. 7, 11, 31 and 34, lacquer barium by D&C Red No. 12, strontium lacquer D&C Red No. 13, aluminum lacquers by FD&C Yellow No. 5, FD&C Yellow No. 6, D&C Red No. 27, D&C Red No. 21, from FD&C Blue No. 1, iron oxides, violet from

  manganese, chromium oxide and ultramarine blue.

  The fillers can be of natural or synthetic origin.

  than. Among these, there may be mentioned in particular: a) mineral powders such as talc, kaolin,

  mica, silica, silicates, alumina, zeolites, hy-

  droxyapatite, sericite, micatitanes, barium sulphate,

  bismuth oxychloride, boron nitride and metal powders

  liquids such as aluminum powder;

  b) vegetable powders such as amine powders

donation of corn, wheat or rice;

  c) organic powders such as ny powders

  lon, polyamide, polyester, polytetrafluoroethylene or polyethylene. These different powders can also be coated, for example, with metal salts of fatty acids, amino acids, lecithin, collagen, silicone compounds,

  fluorinated compounds or by any other usual coating.

-5-

  In addition to the pigments as defined above, the

  positions may further contain at least one dye and, per-

  among these, there may be mentioned eosin derivatives such as D&C Red No. 21 and halogenated fluorosceine derivatives such as D&C Red No. 27, D&C Orange No. 5 in combination with D&C Red No. 21

and the D&C Orange No. 10.

  In make-up compositions or so-called product

  the proportion of at least one pigment and / or dye is large

  generally between about 0.1 and 15% by weight relative to

the total weight of the composition.

  The charges can generally be present in the

  make-up or sunscreen products in a maximum proportion of

  about 98% by weight relative to the total weight of the composition.

  According to a first particular embodiment of the

  make-up or sunscreen positions, these are an-

  hydrous and comprise a fatty phase in a proportion of between approximately 0.3 to 90% by weight relative to the total weight of the composition.

  The fatty phase generally consists of one or more

  certain fatty substances which can be chosen from oils,

  waxes, gums and / or fatty substances called pasty.

  A - The oils of the fatty phase can be of mineral, animal, vegetable or synthetic origin, these can be

  volatile or not at room temperature.

  As mineral oil, mention may be made in particular of

  paraffin oil and petroleum jelly oil.

  As oil of animal origin, mention may be made in particular of

  ment the squalane or perhydrosqualene.

  As vegetable oil, mention may be made in particular of

  ment of sweet almond oil, calophyllum oil, palm oil, avocado oil, jojoba oil, sesame oil,

  olive oil, castor oil and seed germ oils

  real such as for example wheat germ oil.

  As synthetic oil, there may be mentioned in particular: (1) the esters of formula (III) below:

R1-COOR2 (III)

  In which: R1 represents the remainder of a higher fatty acid having from 7 to 20 carbon atoms and R2 represents a hydrocarbon radical having from 3 to 30 carbon atoms. Among these esters, there may be mentioned in particular:

  Purcellin oil, butyl myristate, iso- myristate

  propyl, cetyl myristate, isopropyl palmitate,

  butyl stearate, hexadecyl stearate, iso- stearate

  propyl, octyl stearate, isoketyl stearate, decyl oleate, hexyl laurate, isononyl isononanoate,

  lanolic acid esters such as isopropanolanolate

pyle and isocetyl lanolate.

  As other synthetic oils, mention may be made of

  in addition to isododecane, isohexadecane, polyisobutenes and po-

  hydrogenated lyisobutene as well as acetylglycerides, octanoa-

  tes and decanoates of polyalcohols such as those of glycol and glycerol, ricinoleates of alcohols and polyalcohols such as that of cetyl alcohol, propylene glycol dicaprylate and diisopropyl adipate;

  (2) fatty alcohols such as oleic alcohol, al-

  cool linoleic, linolenic alcohol, isostearyl alcohol and octyldodecanol;

  (3) silicone oils such as polydiorga-

  optionally functionalized linear nosiloxanes, poly-

  cyclic diorganosiloxanes and in particular cyclotetra- and pentadimethicones and organopolysiloxanes such as alkyl,

  alkoxy or phenyl dimethicones and in particular phenyltrimethi-

  cone; (4) non-volatile fluorinated oils such as perfluorodecaline, perfluorophenanthrene, perfluoroalkanes

  and perfluoropolyethers and partial hydrocarbon oils-

fluoridated.

  According to a particularly preferred form of the invention

  tion, non-volatile perfluoropolyethers corresponding to the following formulas (IV) and (V) are used: -7- CF3 (-

1) F - CF-CF2-O CF2-CF3 IV)

in which: n = 7 to 30, CF;

2) CF3 -O-CF-CF2 O-CF OCF3 (V)

in which:

n and m = 20 to 40.

  Among these may be mentioned those sold under the

  nominations of "FOMBLIN C" and "GALDEN" by the AUSSIMONT Company, or even under the name "FLUORTRESS LM 36" by the

DU PONT Company.

  B - The waxes of the fatty phase can be of mineral, fossil, animal, vegetable, synthetic origin or even

  be hydrogenated oils or concrete fatty esters at 25 C.

  Among the mineral waxes, there may be mentioned in particular

  microcrystalline waxes, paraffin, petrolatum and cereal

  sine. Among the fossil waxes, there may be mentioned ozokerite

and montan wax.

  Among the waxes of animal origin, mention may be made of beeswax, spermaceti, lanolin wax as well as lanolin derivatives such as lanolin alcohols, hydrogenated lanolin, hydroxylated lanolin, acetylated lanolin ,

  lanolin fatty acids and acetylated lanolin alcohol.

  Among the waxes of vegetable origin, we can cite our-

  especially candellila wax, carnauba wax, Ja- wax

pon and cocoa butter.

  Among the synthetic waxes, mention may in particular be made of homopolymers of ethylene and copolymers of ethylene and of a monomer corresponding to the following formula (VI):

CH2 = CH-R3 (VI)

  in which: R represents an alkyl radical having from 1 to 30 atoms -8-

  of carbon, an aryl or aralkyl radical.

  The alkyl radical having from 1 to 30 carbon atoms is preferably the methyl, ethyl, propyl, isopropyl radical,

  butyl, decyl, dodecyl or octadecyl.

  It is also possible to use the waxes obtained by

  Fisher-Tropsch synthesis as well as silicone waxes.

  Among the hydrogenated oils which are concrete at 25 ° C., there may be mentioned in particular hydrogenated castor oil, palm oil

  hydrogenated, hydrogenated tallow and hydrogenated coconut oil.

  Among the fatty esters which are concrete at 25 ° C., there may be mentioned in particular propylene glycol monomyristate and myristyl myristate. As waxes which can be used in the compositions according to the invention, mention may also be made of cetyl alcohol, stearyl alcohol, mono-, di- and triglycerides concrete at 25 ° C., stearic monoethanolamide, rosin and its derivatives such as abietates of glycol and glycerol, the sugar glycerides and

  oleates, myristates, lanolates, stearates and dihydroxystéara-

  calcium, magnesium, zinc and aluminum.

  According to a preferred embodiment, fluorinated polyesters corresponding to the following formula (VII) are used as wax:

O O

  It I1 CF- (CF2) r- (CH2) O-C-A- -C-O- (CH2) - (CF2) -CF3 (VII) R4 in which: R4 represents a hydrogen atom or the radical O 1 l

-C-O- (CH2) - (CF2) -CF3

  A is an alkyl or alkenyl chain, linear or ra-

  mified, optionally hydroxylated, having from 1 to 18 carbon atoms

bone, m is 1 to 4, and

n is 3 to 17.

  C - The pasty type fatty substances may be of origin -9-

  mineral, animal, vegetable or synthetic.

  Among the pasty fatty substances, there may be mentioned in particular

  synthetic esters such as arachidyl propionate, po-

  vinyl lylaurate, polyethylene waxes and organopoly-

  siloxanes such as alkyldimethicones, alkoxydimethicones

or dimethicone esters.

  The anhydrous compositions as defined above, can of course also contain one or more additives

  or conventional cosmetic or dermatological adjuvants.

  These anhydrous compositions can be presented under different

  ferent forms such as, for example, an oily gel, a

  solid product such as a compacted or poured powder, or else

  core of a stick such as for example a lipstick.

  When the compositions are in the form of an oil gel

  they generally contain, in addition to the constituents

  nis previously, an oily gelling agent.

  Among the oily gelling agents, there may be mentioned in particular metal esters such as polyoxyaluminum stearate and aluminum or magnesium hydroxystearate, fatty acid and glycol esters, triglycerides, mixtures of fatty alcohols, cholesterol derivatives and in particular hydroxycholesterol,

  and swelling clay minerals in the presence of oil and in par-

  especially those belonging to the group of montmorillonites.

  Oily gelling agents may be present in a pro-

  very variable portion depending on the texture of the compositions sought-

  chée. However, in most cases, they are present in a proportion of between about 0.1 and 30% by weight relative to

the total weight of the composition.

  These anhydrous compositions can in particular be foundations, mascaras, eyeliners, lipsticks,

  eyeshadows or blushes.

  According to a second embodiment of the compositions according to the invention, these are dispersions, in the form of a stable water-in-oil (W / O) or oil-in-water (H / E) which essentially consist of (i) a fatty phase in a proportion of between approximately 0.1 and 50% by weight per - 10 -

  relative to the total weight of the composition, said fatty phase can

  before containing at least one fatty substance as defined above in a proportion of between approximately 0.1 and 95% by weight relative to the total weight of the composition, (ii) of an aqueous phase in a proportion of between approximately 4 and 97% by weight relative to the total weight of the composition, and (iii) at least one emulsifying agent in a proportion of between approximately 1 and% by weight relative to the total weight of the composition under

emulsion form.

  As an emulsifier or surfactant which can be used

  read in the compositions in the form of a W / O or O / W emulsion, mention may in particular be made of silicone surfactants, and

  especially those belonging to the family of alkyl- or alkoxydi-

  methicone copolyols. Among the alkyl- or alkoxydimethicone copo-

  lyols, mention may in particular be made of the compounds corresponding to the following general formula:

CH. CH CH3 CH3 CH3

CHR SiO - SiO SiO Sio si -CH3 (IV)

CH: CH3 (CH2) 3 R 'CH3

  _ _ u 0- (C2H40O (C: H60) v _ _W in which: R is a hydrogen atom, a C1-C16 alkyl, an alkoxy or acyl, R 'is a C8-C22 alkyl or alkoxy radical , u = 0 to 200, v = 1 to 40, w = 1 to 100, the molecular weight of the radical -O- (C2H40) X (C3H60) 7R being from 250 to 2000, x and y being chosen such that the weight ratio of the oxyethylene / oxypropylene groups is understood

between 100: 0 and 20:80.

  Among the commercial products which may contain all or part of the alkyldimethicones copolyols, mention may be made in particular of: - Those sold under the names of "ABIL WE09" R) I, "ABIL EM90D)" or "ABIL WSO8 R '" by the company GOLDSCHMIDT , from "Q2 5200 C" or "Q2 3225C, .v" by the company DOW CORNING and from "218 1138 (" by the

GENERAL ELECTRIC.

  The surfactants can also be chosen from anionic or nonionic surfactants. We can

  see the document "Encyclopedia of Chemical Tech-

  nology, KIRK-OTHMER ", volume 22, pages 333-432, 3rd edition, 1979

  WILEY, for the definition of properties and functions (emul-

  surfactants), especially pages 347-377 of this

  reference, for anionic and nonionic surfactants.

  The surfactants of these two groups used preferably

  Rence in the compositions according to the invention are: - from nonionic surfactants: fatty acids,

  fatty alcohols, polyethoxylated or polyglycerolated fatty alcohols

  strips, such as poly (stearyl or cetylstearyl) alcohols

  ethoxylates, fatty acid and sucrose esters, alkyl glucose esters, in particular fatty esters of polyoxyethylenated alkyl (Cl-C6) glucose, and - among anionic surfactants: amine stearates. These emulsions are preferably in the form of creams and can be used as make-up products or

  sun products. In the latter case, they contain threads

  very sun UVA and / or UVB as well as white pigments, in one

  variable proportion depending on the degree of protection sought.

  The compositions as described above, whether they are of the anhydrous type or in the form of a dispersion, have

  excellent cosmetic properties such as in particular an ex-

  excellent ease of application, great softness and conduct

  obtaining a uniform makeup.

  The compositions as just described above, can also contain one or more conventional cosmetic adjuvants such as vitamins, hormones, antioxidants, preservatives, perfumes, thickeners, moisturizers, humectants, anionic, nonionic or amphoteric polymers, or active ingredients

cosmetic or dermatological.

  The invention will now be illustrated by the various

  following examples, the amounts of which are expressed by weight.

EXAMPLES

  EXAMPLE 1 Transfer-resistant lipstick - Nanofluoromethoxybutane (MSX 4518) .......................... 10 g Perfluorodecaline ...... ..................................................

  .35 g - 2-F octylethyl dodecanedioate ............................. .40 g - Polyperfluoroisopropylether (FLUORTRESS LM 36). .................. .DTD: ............................. ........... 5 g - Pigments ...... DTD: ........................... ............................... 10 g After hot mixing of fatty substances, at a temperature lower than that of evaporation volatile oil, the pigments are introduced with stirring, and the melted mixture is then poured..DTD: into lipstick molds.

  After cooling and demolding, lipsticks of good texture are obtained having good ease of application and a very short drying time. We also note,

  that after drying, the lipstick does not give rise to any pheno-

  transfer leads according to the conventional tests used for this

type of determination.

  EXAMPLE 2: Foundation - Perfluoromethylcyclopentane (FLUTEC PC 1) ....

  .... 20 g - Alkyldimethicone copolyol (ABIL WE 09) ................. 5 g Cyclomethicone ................ ..................... 10 g - Pigments ... .DTD: ................... ............................ 7 g - Water ..... DTD: ........... ............................ qs 100 g -13 - This foundation is obtained in the form of a water-in-oil emulsion (W / O) by mixing, with stirring, the fatty phase and the aqueous phase. This gives a foundation of good consistency, which is easy to apply and whose drying time is very fast. It is particularly resistant to friction. -14 -... DTD:

Claims (6)

CLAIMS l. it.saEzon in a cosmetic composition for making up or: sunscreening, containing pigment and / or filler particles, of at least one volatile fluorinated solvent, as anti-transfer agent, said fluorinated solvent having a vapor pressure greater than 20 mba (2000 Pa) at 25 C.   2. Use according to claim 1, characterized   by the fact that said fluorinated solvent is a perfluorocyte compound   cloalkyle corresponding to the following formula: (CF2) n (CF- (CF2) p-F) m (I) in which: n is 4 or 5, m is 1 or 2, and p is 1, 2 or 3   provided that when m = 2, the groupings are not necessary   obviously in alpha, relative to each other.   3. Use according to claim 2, characterized in that the perfluorocycloalkyl compound is chosen from   group consisting of perfluoromethylcyclopentane and perfluo-   romethylcyclohexane. 4. Use according to claim 1, characterized   by the fact. that said fluorinated solvent is a fluorinated alkyl ether   having the following formula: CH3- (CH2) n-0- (CF2) m-CF3 (II) in which: n es; 0, 1, 2 or 3, and m is 2, 3, 4 or 5.   5. Use according to claim 4, characterized   because the fluorinated alkyl ether is nanofluoromethoxvbu- tane.   -. Use according to any one of the claims   previous: s, -ara.zerized by the fact that the fluorinated solvent vola-   it is present in the composition in a proportion comprised between- - l 5.2773065   be 2 and 98 by weight relative to the total weight of the composition tion.   Use according to any of the claims   precedentes, characterized in that the proportion of pigment and / or dye in the composition is between 0.1 and 15   by weight relative to the total weight of the composition.   8. Use according to any one of claims   above, characterized in that the proportion of filler in the composition is at most 98% by weight relative to the total weight of the composition.   9. Use according to any one of claims   above, characterized in that the cosmetic composition   that is anhydrous and comes in the form of a foundation, a mascara, an eyeliner, a lipstick, an eyeshadow or cheek for makeup.   10. Use according to any one of the claims   1 to 8, characterized in that the cosmetic composition is a water-in-oil or oil-in-water emulsion and is in the form of a cream for make-up or for protection solar.