JP2015523959A - Cosmetic composition comprising supramolecular polymer, non-volatile silicone oil and non-volatile hydrocarbonated oil - Google Patents

Abstract

The present invention relates to the formula HO-P-OH, wherein P is one or more of linear, cyclic and / or branched polyunsaturated C2-C10 alkenes, preferably C2-C4 alkenes. Represents a homopolymer or copolymer obtainable by polymerization, which is functionalized with at least one reactive group capable of reacting with the functionalized polyalkene polymer and a reactive group of the functionalized polyalkene polymer. It is possible to derive from reaction with a linking group, in particular from condensation, said linking group having at least 3 H (hydrogen) bonds, preferably at least 4 H bonds, preferentially 4 H bonds. Capable of forming] at least one supramolecular polymer based on a functionalized polyalkene; at least one, preferably phenylated, non-volatile silicone oil, and at least one non-volatile Hydrocarbons , Preferably a non-polar hydrocarbon oils, about the skin and / or for making up the lips and / or the composition for caring.

Description

  The present invention relates to cosmetic compositions, and more particularly to make up and / or care for skin and / or lips comprising at least one supramolecular polymer, non-volatile silicone oil and non-volatile hydrocarbonated oil. The present invention relates to a cosmetic composition.

  The invention also relates to a method of using such a composition for making up and / or caring for the skin and / or lips, the method applying such a cosmetic composition to the skin and / or lips. Process.

  In general, when women use lip product makeup products, especially lipstick or lip gloss types, they find that the product is easy to apply and comfortable on the skin or lips after application. And there is good persistence, specifically no migration, and in particular no color migration or a low amount of color migration.

  With respect to this expectation, one or more polymers specifically aimed at providing these improved aging properties are generally introduced into this type of composition. Illustrative of these polymers that may be specifically mentioned are silicone resins, polyacrylates and latexes.

European Patent No. 2189151 French Patent No. 2938758 French Patent No. 2782723 International Publication No. 2005/042641 French Patent No. 0853634 European Patent No. A-847752 US Patent No. 7470725 European Patent No. A-542669 European Patent No. A-787730 European Patent No. A-787731 International Publication No. A-96 / 08537 French Patent Application No. 2829344

C.M.Hansen, `` The three dimensional solubility parameters '', J. Paint Technol., 39, 105 (1967) CTFA (6th edition, 1995) Brinker C.J. and Scherer G.W., Sol-Gel Science, New York, Academic Press, 1990 "The Journal of the American Chemical Society", Volume 60, 309, February 1938 Van de Hulst, H.C., "Light Scattering by Small Particles" Chapters 9 and 10, Wiley, New York, 1957

  However, the above-mentioned polymers, which are advantageous in terms of residual properties, in particular color transfer resistance, unfortunately cause discomfort during application of cosmetic products containing the polymer (difficult to spread and sticky ) And / or after application (tiffness, mask effect).

  On the other hand, supramolecular polymers such as those described in European Patent No. 2189151 and French Patent No. 2938758 have improved comfort and improved residual properties over time, especially sediment color persistence (deposits). It is known that deposits can be produced on the skin or lips, both with the application of (and remain uniform, without embrittlement or fragmentation). However, users have a “sticky” and dry sensation while applying products incorporating these supramolecular polymers onto the skin or onto the lips. Moreover, deposits formed from galenical formulations incorporating such supramolecular polymers may have insufficient mechanical strength.

  The inventors have unexpectedly found that this drawback can be overcome when such supramolecular polymers are used in combination with at least one non-volatile silicone oil and non-volatile hydrocarbon oil. It has become clear.

  The aim of the present invention is to overcome these drawbacks and to be homogeneous and stable (especially after 24 hours at room temperature and even after 72 hours at room temperature, for example, separation of the pigment into two phases and On the other hand, good cosmetic properties (specifically, application properties such as slip and ease of application, especially on the lips, to the support (skin or lips)) Good adhesion of the composition, and thereby good persistence of the deposit of the composition, in particular, no or low amount of color transfer of the deposit, and deposits with little or no stickiness, It is to propose a cosmetic composition capable of providing a good level.

Thus, according to one aspect of the present invention, the present invention provides a HO-P-OH, wherein P is one or more, linear, in a physiologically acceptable medium. cyclic and / or branched polyunsaturated C ₂ -C ₁₀ alkene, preferably represents a homopolymer or copolymer obtainable by polymerization of C ₂ -C ₄ alkene, which includes: the functionalized polyalkene polymers, It can be derived from reaction with at least one linking group functionalized with at least one reactive group capable of reacting with a reactive group of the functionalized polyalkene polymer, in particular from condensation, said linking group being At least 3 H (hydrogen) bonds, preferably at least 4 H bonds, preferentially 4 H bonds can be formed] at least one supramolecular polymer based on functionalized polyalkenes At least one, preferably phenylated To a cosmetic composition for making up and / or caring for the skin and / or lips, comprising a non-volatile silicone oil, and at least one, preferably non-polar, non-volatile hydrocarbonated oil .

  Such a composition is stable and homogeneous, preferably its deposit on the keratinous material, in particular on the lips and / or skin, is easy, uniform and has a good level of shine, Good persistence (no deposit embrittlement or fragmentation), good color transfer resistance after application (especially in cups or glasses, especially during drinking) Makeup compositions with little or no color transfer) and / or little or no tackiness. Such deposits can provide a particularly comfortable feeling to the wearer.

  The invention also relates to a cosmetic method for making up and / or caring for the skin and / or lips, said method being defined on at least one in at least a physiologically acceptable medium. Applying to the skin and / or the lips a composition comprising a supramolecular polymer, at least one non-volatile silicone oil, and at least one non-volatile hydrocarbonated oil.

  Advantageously, the composition under investigation according to the invention is an oil-in-oil composition. In the oil-in-oil type composition of the present invention, the non-volatile silicone oil and the non-volatile hydrocarbon oil are in a stable oil-in-oil state before application and do not separate from each other. After application, non-volatile silicone oil rises to the surface of the deposit, and this separated non-volatile silicone oil covers the adherent layer of non-volatile hydrocarbonated oil and supramolecular polymer. The resulting composition therefore has good transfer resistance and imparts a good level of shine. This separation is further facilitated by rubbing the upper and lower lips again during application.

  Advantageously, the composition under investigation according to the invention is an anhydride. Advantageously, the at least one non-volatile silicone oil is selected from non-volatile linear phenyl silicone oils.

  Advantageously, the at least one non-volatile hydrocarbonated oil is selected from nonpolar non-volatile hydrocarbonated oils.

Physiologically Acceptable Medium For the purposes of the present invention, the term “physiologically acceptable medium” is usually used in a medium suitable for applying the composition to the skin and / or lips, eg a cosmetic composition. It is contemplated to indicate the oil or organic solvent used.

  The physiologically acceptable medium (acceptable, tolerance, toxicity and feel) is generally adapted to the nature of the support on which the composition is to be applied, and where the composition is conditioned Adapted to different forms.

  As will emerge from the following examples, the combination under consideration by the present invention imparts to the composition a deposit on the skin or lips that simultaneously improves its glossy and color-free properties. Has been found to be most particularly effective. Apart from that, the deposit also exhibits a persistence over time, in particular a deposit color persistence (no embrittlement or fragmentation of the deposit occurs and remains homogeneous) and satisfactory comfort. It exhibits excellent properties when applied (especially slipperiness, disintegration, density and uniformity of the formed sediment, and reduced stickiness upon drying) and when worn (i.e., softness, sticky sensation) Or absence of stringency or dry sensation).

  Beyond that, in the case of lipsticks (solid or liquids such as gloss), this improvement of no color transfer and no stickiness or slight was not obtained at the expense of shine, but shine. Is another property that is commonly explored in this type of makeup product. In particular, contrary to all expectations, the matte effect of cosmetic products containing the combination under investigation according to the invention has not been observed.

  The invention also provides at least one supramolecular polymer, at least one non-volatile silicone oil, at least one non-volatile hydrocarbonated oil, and at least one colorant in a physiologically acceptable medium. Also preferably relates to a composition for making up and / or caring for the skin and / or lips.

  The composition under investigation according to the invention and used in the process according to the invention can be in solid or liquid form at 20 ° C.

  In a preferred embodiment, especially in the case of compositions intended to care and / or make up the lips, the composition used according to the invention is anhydrous or relative to the total mass of the composition Less than 3% by weight water, preferably less than 1% by weight water.

  The term “anhydride” specifically means that water is preferably not intentionally added to the composition, but may be present in trace amounts in the various compounds used in the composition.

  The composition according to the invention and / or the composition used according to the method according to the invention is in the form of a composition for making up the skin and / or lips, in particular for facial or body skin. Well, this is a product for facial gloss such as foundation, face powder, eye shadow, etc .; products for lips such as lipstick, lip care products; concealer products; blusher; eyeliner; lip pencil or eye pencil; body makeup Up product; can be gloss (lip gloss).

  According to an advantageous first embodiment of the invention, the composition is intended to make up the lips, more particularly a lipstick (stick lipstick) or gloss (liquid lipstick).

  Advantageously, the lipstick composition according to the invention is anhydrous.

For the purposes of the present invention, the term “solid” characterizes the state of the composition at a temperature of 20 ° C. In particular, the solid compositions according to the invention, at a temperature 20 ° C. and atmospheric pressure (760 mmHg), ^-1 greater hardness 30 Nm, preferably 35 Nm ^-1 greater.

Protocol to measure hardness

  Lipstick sticks are stored at 20 ° C. 24 hours prior to hardness measurement.

  Hardness can be measured at 20 ° C. via the “cheese wire” method, which is a product that is preferably a cylinder by moving the wire at a speed of 100 mm / min with a hard tungsten wire with a diameter of 250 μm. Consisting of cutting the bar horizontally.

The hardness represented by Nm ⁻¹ of the sample of the composition of the present invention is measured using a DFGHS2 tensile tester manufactured by Indelco-Chatillon.

  The measurement is repeated 3 times and then averaged. The average of the three values read using the above tensile tester is marked Y and shown as grams. This average is converted to Newton and then divided by L, which represents the longest distance that the wire will pass. In the case of a cylindrical bar, L is equal to the diameter (in meters).

The hardness is converted to Nm ^-1 by the following formula:
(Y × 10 ^-3 × 9.8) / L

  To measure at different temperatures, the stick is stored for 24 hours at this new temperature before measurement.

According to this measuring method, the solid compositions according to the present invention, the hardness at 20 ° C. is, 30 Nm ^-1 or more, preferably 35 Nm ^-1 greater, preferably 40 Nm ^-1 greater.

Preferably, the composition according to the present invention, in particular, less than hardness 500 Nm ^-1 at 20 ° C., in particular 400Nm less than ^-1, preferably less than 300 Nm ^-1.

In particular, a composition whose hardness is greater than 30 Nm ⁻¹ at 20 ° C. and atmospheric pressure (760 mmHg) is said to be “solid”.

  According to a preferred embodiment, the composition according to the invention is liquid at 20 ° C.

Protocol for measuring viscosity:
Viscosity measurements are generally performed at 25 ° C. using a Rheomat RM180 equipped with a No. 4 spindle, which is measured 10 minutes after rotation of the spindle in the composition (at this time, viscosity stabilization and Stabilization of the rotation speed of the spindle is observed) and the shear rate is 200 rpm.

  Preferably, the composition has a viscosity at 25 ° C. of between 1 and 25 Pa.s, preferably between 2 and 20 Pa.s, preferably between 4 and 17 Pa.s.

  Preferably, the viscosity at 25 ° C. of the composition according to the invention is between 5 and 16 Pa.s.

  The terms “between” and “within” should be understood to include upper and lower values.

  The following examples are given by way of illustration and have no limiting nature.

  The invention also encompasses a cosmetic method for making up and / or caring for the lips, which method comprises at least the step of applying a composition as defined above to the lips.

Supramolecular polymer The cosmetic composition according to the invention therefore comprises a supramolecular polymer based on polyalkenes (ie of polyolefins).

  For the purposes of the present invention, the term “polyalkene-based supramolecular polymer” refers to the reaction of at least one polyalkene polymer functionalized with at least one reactive group with the reactive group of the functionalized polyalkene polymer. It is possible to derive from reaction with at least one linking group functionalized with at least one reactive group possible, in particular from condensation, said linking group being at least 3 H (hydrogen) bonds, preferably Means a polymer capable of forming at least 4 H bonds, preferentially 4 H bonds.

  The term “polyalkene” or “polyolefin” means a polymer derived from the polymerization of at least one alkene-type monomer (possibly pendant or within the main chain of the polymer) containing ethylenic unsaturation. Thus, the term “polyalkene” or “polyolefin” refers to a polymer that may or may not contain double bonds. Preferably, supramolecular polymers used in accordance with the present invention are prepared from polymers derived from the polymerization of alkenes containing at least two ethylenic unsaturations.

  The supramolecular polymer according to the invention forms a chain or network of supramolecular polymers by (self) assembly of the polymer according to the invention with at least one other identical or different polymer according to the invention. Each set includes at least one pair of identical or different, paired linking groups carried by each of the polymers according to the invention.

  For the purposes of the present invention, the term “linking group” includes at least 3 H bonds, preferably at least 4 H bonds, preferentially in the same or different partner linking groups, including groups that donate or accept H bonds. Means any group including groups capable of forming four H bonds. These linking groups may be located on the side (side branch) of the polymer main chain and / or held by the ends of the polymer main chain and / or within the chain forming the polymer main chain. May be located. The linking groups can be distributed randomly or in a controlled manner.

Functionalized polyalkene The polyalkene polymer is functionalized with at least one reactive group, preferably with at least two reactive groups. Functionalization preferably takes place at the end of the chain. In that case, they are referred to as telechelic polymers.

Functional groups or reactive groups, through a linker, is preferably via a linear or branched C ₁ -C ₄ alkylene group, or directly through a single bond, adhere to the polyalkene polymer sell.

  Preferably, the functionalized polyalkene polymer has a number average molecular weight (Mn) of between 1000 and 8000.

  Even more preferably, they have a number average molecular weight between 1000 and 5000, or even between 1500 and 4500.

  Even more preferably, they have a number average molecular weight between 2000 and 4000.

Preferably, the functionalized polyalkene polymer capable of forming all or part of the polymer backbone of the supramolecular polymer according to the invention (preferably it forms all of the polymer backbone) has the formula HO-P- OH
[Where
P is one or more linear, cyclic and / or branched, polyunsaturated (preferably diunsaturated) C ₂ -C ₁₀ alkenes, preferably by polymerization of C ₂ -C ₄ alkene Represents a homopolymer or copolymer that can be obtained]
belongs to.

P preferably represents one or more linear, homopolymers or copolymers obtainable by polymerization of cyclic and / or branched di-unsaturated C ₂ -C ₄ alkene.

  More preferably, P is a polymer selected from polybutylene, polybutadiene (e.g., 1,4-polybutadiene or 1,2-polybutadiene), polyisoprene, poly (1,3-pentadiene) and polyisobutylene, and copolymers thereof. Represent.

  According to one preferred embodiment, P represents a poly (ethylene / butylene) copolymer.

A preferred poly (ethylene / butylene) is a copolymer of 1-butene and ethylene. These can be represented schematically by the sequence of the following units:
[-CH ₂ -CH _2- ] and [-CH ₂ CH (CH ₂ -CH ₃ )-]

According to a second preferred embodiment, P is a polybutadiene homopolymer preferably selected from 1,4-polybutadiene or 1,2-polybutadiene. The polybutadiene may be 1,4-polybutadiene or 1,2-polybutadiene, each of which can be schematically represented by the following arrangement of units:
[-CH ₂ -CH = CH-CH _2- ] (1,4-polybutadiene)
[-CH ₂ -CH (CH = CH ₂ )-] (1,2-polybutadiene)

  Preferably P is 1,2-polybutadiene. Preferably P is a 1,2-polybutadiene homopolymer.

  According to another embodiment, P is polyisoprene. Polyisoprene can be schematically represented by the following sequence of units:

  Mixtures of the above units can also obviously be used to form copolymers.

  The functionalized polyalkene polymer may be totally hydrogenated to avoid the risk of crosslinking. Preferably, the functionalized polyalkene polymer used in the composition according to the invention is hydrogenated.

  Preferably, the polyalkene polymer is hydrogenated and functionalized with at least two OH reactive groups, preferably at the ends of the polymer.

  Preferably, they have a hydroxyl end group functionality of about 1.8 to 3, preferably about 2.

  Polydienes having hydroxyl end groups are specifically defined, for example, in French Patent No. 2782723. These can be selected from homopolymers and copolymers of polybutadiene, polyisoprene and poly (1,3-pentadiene). Mention may be made in particular of hydroxylated polybutadienes sold by the company Sartomer, such as Krasol® resin and Poly bd® resin. Preferably, they are in the range of dihydroxylated hydrogenated 1,2-polybutadiene homopolymers such as Nisso-PB1, GI3000, GI2000 and GI1000 sold by Nippon Soda Co., which have the formula Can be represented schematically:

Preferably n is between 14 and 105, preferably between 20 and 85.
These polymers have the following number average molecular weights: GI3000 has Mn = 4700, GI2000 has Mn = 3300, and GI1000 has Mn = 1500. These values are measured by GPC according to the following protocol:

Protocol for measuring molecular weight of supramolecular polymers by GPC:
Number average in polystyrene equivalents

Molecular weight, mass average

Molecular weight and polydispersity index

Quantitative.

Standard Solution Preparation Polystyrene standards are prepared from Varian kits [see PS-H (PL2010-0200)].
The mass of the reference material is as follows:
PS6035000-PS3053000-PS915000-PS483000-PS184900-PS60450-PS19720-PS8450-PS3370-PS1260-PS580
Inject 100 μl of each solution into the calibration column.

Sample preparation
Prepare a 0.5% solids solution in THF.
Prepare solution for approximately 24 hours prior to injection.
Filter the solution through a Millex FH filter (0.45 μm).
Inject into the column.

Chromatographic condition column: PL Rapid M (Batch 5M-Poly-008-15) manufactured by Polymer Labs
PL-gel HTS-D (Batch 5M-MD-72-2) manufactured by Polymer Labs
PL-gel HTS-F (10M-2-169B-25) manufactured by Polymer Labs
PL-Rapid-F (6M-0L1-011-6) manufactured by Polymer Labs
Length: 150mm-Inner diameter: 7.5mm
Pump: isocratic M1515 Waters
Eluent: THF
Flow rate: 1 ml / min Temperature: Room temperature Injection: 100 μl at 0.5% AM in eluent
Detection: RI 64mV (Waters 2424 Refractometer) Temperature: 45 ° C
UV at 254nm at 0.1OD (Waters2487 UV detector)
Integrator: Empower option GPC

Quantification of molar mass The average molar mass is determined by plotting a calibration curve: log molar mass = f (volume of eluent at the peak of the RI detection peak), using the software Empower option GPC from Waters.

  Among the polyolefins having hydroxyl end groups, preference may be given to polyolefins, homopolymers or copolymers having α, ω-hydroxyl end groups, such as polyisobutylene having α, ω-hydroxyl end groups, and Is a copolymer of the formula:

Specifically, it is sold by Mitsubishi Chemical Corporation under the trade name Polytail.

Linking groups The supramolecular polymers according to the invention also have in their structure at least one residue of a linking group capable of forming at least 3 H bonds, preferably at least 4 H bonds, The linking group is first functionalized with at least one reactive group.

  Unless otherwise specified, the term “linking group” means herein a group that does not have that reactive functional group.

  The reactive group is attached to the linking group via the linker L.

L represents a single bond, or a C ₁ -C ₂₀ divalent carbon-based radical saturated or unsaturated, specifically, straight-chain or branched C ₁ -C ₂₀ alkylene, C ₅ -C ₂₀ (alkyl) cycloalkylene alkylene (preferably cyclohexylene-methylene), C ₁₁ -C ₂₀ alkylene - bis cycloalkylene (preferably alkylene - bis cyclohexylene), C ₆ -C ₂₀ (alkyl) arylene, alkylene - bisarylene (preferably The linker L is presumably substituted with at least one alkyl group and / or 1 to 4 N and / or O, especially in the form of a NO ₂ substituent. Probably contains heteroatoms.

Preferably, the linker is phenylene, 1,4-nitrophenylene, 1,2-ethylene, 1,6-hexylene, 1,4-butylene, 1,6- (2,4,4-trimethylhexylene), 1 , 4- (4-methylpentylene), 1,5- (5-methylhexylene), 1,6- (6-methylheptylene), 1,5- (2,2,5-trimethylhexylene), 1 , 7- (3,7-dimethyloctylene), -isophorone-, 4,4'-methylenebis (cyclohexylene), tolylene, 2-methyl-1,3-phenylene, 4-methyl-1,3-phenylene, A group selected from 4,4-biphenylenemethylene;
Preferably, the linker is a group:
- C ₅ ~C ₂₀ (alkyl) cycloalkylene alkylene, for example isophorone,
- C ₁₁ -C ₂₅ alkylene - bis cycloalkylene, for example, 4,4'-methylene-bis-cyclohexene,
- C ₁ -C ₂₀ alkylene, for example _{- (CH 2) 2 -,} - (CH 2) 6 -, - CH 2 CH (CH 3) -CH 2 -C (CH 3) 2 -CH 2 -CH 2, as well as
-C ₆ -C ₂₀ (alkyl) phenylene, for example 2-methyl-1,3-phenylene.
Preferably, L is -isophorone-,-(CH ₂ ) ₂ -,-(CH ₂ ) _6- , -CH ₂ CH (CH ₃ ) -CH ₂ -C (CH ₃ ) ₂ -CH ₂ -CH ₂ 4,4′-methylenebis (cyclohexylene), 2-methyl-1,3-phenylene.

  According to one particularly preferred embodiment, the linker is alkylcycloalkylenealkylene.

  Preferably, in this embodiment, the linker is an isophorone group. The term `` isophorone '' means the following groups:

  The reactive group that functionalizes the linking group should be able to react with the —OH reactive group carried by the functionalized polyalkene.

  Among the reactive groups that may be mentioned are isocyanate (—N═C═O) groups and thioisocyanate (—N═C═S) groups. Preferably it is a —N═C═O (isocyanate) group.

  The functionalized linking group capable of forming at least 3 H-bonds can comprise at least 3 identical or different functional groups, preferably at least 4 functional groups, selected from :

These functional groups can be divided into two categories:
-Functional groups donating H bonds:

-Functional groups that accept H bonds:

  A linking group capable of forming at least 3 H-bonds is a base structural element comprising at least 3 groups capable of establishing H-bonds, preferably at least 4 groups, more preferentially 4 functional groups Form. Said base structural element capable of establishing H-bonding can be schematically represented in the following manner:

[Wherein X _i is a functional group that accepts an H bond (same or different), and Y _i is a functional group that gives an H bond (same or different).

  Thus, each structural element is identical such that two partner structural element pairs each occur by the formation of at least 3 H bonds, preferably at least 4 H bonds, and more preferentially 4 H bonds. It must be possible to establish H-bonds with one or more partner structural elements, ie self-complementary) or different.

Proton acceptor X is paired with proton donor Y. Thus, multiple possibilities are offered, for example, the following pairs:
XXXX and YYYY,
XXXY and YYYX,
XXYX and YYXY,
XYYX and YXXY,
XXYY and YYXX self-complementary or not,
XYXY and YXYX self-complementary or not.

  Preferably, the linking group can establish four H-bonds with the same (or self-complementary) partner group, of which two are donor bonds (e.g. NH) and two Is receptor binding (eg CO and -C = N-).

Preferably, linking groups capable of forming at least 4 H bonds are selected from the following families and are understood to include all tautomeric forms:
-(i) Ureidopyrimidone of the following formula (can form at least 4 H bonds)

[Wherein the radicals have the following meanings:
-R ₁ group (or R ₁ and R ₂ groups) constitutes the attachment point of the linking group to a linker capable of forming at least 3 H bonds (preferably 4 H bonds) in the rest of the graft Single bond. Preferably, the attachment point is held only by R ₁ which is a single bond.
The R ₂ group can have a single bond or a divalent group selected from C _{1 to} C ₆ alkylene, or a single bond, a hydrogen atom, or one or more heteroatoms such as O, S or N; a linear or branched monovalent saturated C ₁ -C ₁₀ monovalent radical selected from hydrocarbon radicals, these radicals, hydroxyl, optionally substituted with amino and / or thio functional group ing.

Preferably, the R ₂ group can be a single bond or a monovalent group selected from H, CH ₂ OH and (CH ₂ ) ₂ —OH, CH ₃ ].

According to one particularly preferred embodiment, R ₂ is H.
-R ₃ group represents a monovalent group or a divalent group, specifically, R ₃ is a hydrogen atom, or a straight chain that can have one or more heteroatoms such as O, S or N Or branched monovalent saturated C ₁ -C ₁₀ hydrocarbon-based groups, which groups are optionally substituted with hydroxyl, amino and / or thio functional groups.

Preferably, the R ₃ group can be a monovalent group selected from H, CH ₂ OH and (CH ₂ ) ₂ —OH, CH ₃ .

According to one particularly preferred embodiment, R ₃ is a methyl group.

  According to one preferred embodiment, the linking group is selected from 2-ureidopyrimidone and 6-methyl-2-ureidopyrimidone.

  Preferably, the preferred linking group is 6-methyl-2-ureidopyrimidone.

  Linking groups, particularly ureidopyrimidone linking groups, can be added directly or formed in situ during the process of preparing supramolecular polymers. The first and second preparation methods described below exemplify these two alternative methods, respectively.

  In particular, the functionalized linking group capable of reacting with a functionalized polyalkene polymer to give a supramolecular polymer according to the present invention is preferably of the formula:

(Wherein L is as defined above.
Preferably L is selected from the following groups:
- C ₅ ~C ₂₀ (alkyl) cycloalkylene alkylene, for example isophorone,
- C ₁₁ -C ₂₅ alkylene - bis cycloalkylene, for example 4,4'-methylene-bis-cyclohexane,
- C ₁ -C ₂₀ alkylene, for example _{- (CH 2) 2 -,} - (CH 2) 6 -, - CH 2 CH (CH 3) -CH 2 -C (CH 3) 2 -CH 2 -CH 2, as well as
C ₆ -C ₂₀ (alkyl) phenylene, for example 2-methyl-1,3-phenylene.

Preferably, L is selected from -isophorone-,-(CH ₂ ) _6- , 4,4'-methylenebiscyclohexylene.

  According to one particularly preferred embodiment, the linking group is of the formula:

(Wherein L is isophorone).

  In one particularly preferred embodiment, the supramolecular polymer of the invention corresponds to the formula:

[Where
-L 'and L'', independently of each other, have the meaning given for L above,
-X, X '= O and P has the meaning given for the functionalized polyalkene polymer above).

Preferably L ′ and L ″ are in particular linear or branched C ₁ -C ₂₀ alkylene, C ₅ -C ₂₀ (alkyl) cycloalkylene, alkylene-biscycloalkylene and C ₆ -C ₂₀ ( alkyl) is selected from arylene, a divalent C ₁ -C ₂₀ carbon-based radical saturated or unsaturated. Preferably, L ′ and L ″ are -isophorone-,-(CH ₂ ) ₂ -,-(CH ₂ ) _6- , -CH ₂ CH (CH ₃ ) -CH ₂ -C- (CH ₃ ) ₂ —CH ₂ —CH _{2 represents} a 4,4′-methylenebiscyclohexylene, 2-methyl-1,3-phenylene group.
Preferably, L ′ and L ″ are the same.
Preferably L ′ and L ″ are isophorone groups.
Preferably P is hydrogenated and represents polyethylene, polybutylene, polybutadiene, polyisoprene, poly (1,3-pentadiene), polyisobutylene, or copolymers thereof, in particular poly (ethylene / butylene).
Preferably, P is hydrogenated polybutadiene, preferably hydrogenated 1,2-polybutadiene.

  In one particularly preferred embodiment, the supramolecular polymer of the invention corresponds to formula (A):

  [In the formula (A), n is preferably between 2 and 200, preferably between 10 and 150, preferably between 15 and 100, most preferably between 20 and 70].

Method of Preparation The polymer according to the present invention is prepared via a method commonly used by those skilled in the art, in particular a method of forming a urethane bond between the free OH function of the polyalkene and the isocyanate function carried by the linking group. Can be done.

By way of non-limiting illustration, the first general preparation method consists of the following steps:
-Optionally ensuring that the polymer to be functionalized does not contain any residual water;
The polymer comprising at least two OH-reactive functional groups, whose hydroxyl number can serve as a reference for measuring the progress of the reaction, can be between 60 ° C. and 140 ° C. Heating to temperature,
-Ureidopyrimidone linkages carrying reactive functional groups, in particular isocyanates (for example those described in WO 2005/042641, especially for example compounds with CAS numbers = 32093-85-9 and 7099028-42-2) Adding the group, preferably directly,
-Optionally stirring the mixture under a controlled atmosphere at a temperature of about 90-130 ° C for 1-24 hours;
- monitoring and quenched with complete disappearance of the peak and then the final product to cool to room temperature, the disappearance of the characteristic absorption band of isocyanate (between 2500 cm ^-1 in 2800 cm ^-1) by IR spectroscopy Process.

  The reaction can be monitored by quantifying the hydroxyl functionality and ethanol can also be added to ensure complete disappearance of the remaining isocyanate functionality.

  The reaction can be carried out in the presence of a solvent, in particular in the presence of methyltetrahydrofuran, tetrahydrofuran, toluene, propylene carbonate or butyl acetate. It is also possible to add prior art catalysts for forming urethane bonds. An example that may be mentioned is dibutyltin dilaurate. The polymer can finally be washed and dried or further purified according to the general knowledge of those skilled in the art.

According to a second preferred embodiment of the preparation, the reaction can comprise the following steps:
(i) Preferably, the reaction scheme of the previously dried polymer:
OH-Polymer-OH (1eq.) + NCO-X-NCO (1eq.) → OCN-X-NH- (O) CO-Polymer-OC (O) -NH-X-NCO
Functionalization with diisocyanate according to

The diisocyanate can optionally be in an excess amount relative to the polymer. This first step can be carried out at a temperature between 20 ° C. and 100 ° C. in the presence of a solvent. After the first step, the stirring period can be 1 to 24 hours under a controlled atmosphere. The mixture may optionally be heated. The progress of this first step can be monitored by quantifying the hydroxyl functionality,
Then
(ii) Reaction of the prepolymer obtained above with 6-methylisocytosine of the formula:

This second step can optionally be carried out in the presence of a co-solvent, for example in the presence of toluene, butyl acetate or propylene carbonate. The reaction mixture can be heated from 80 ° C. to 140 ° C. for a period ranging from 1 to 24 hours. The presence of a catalyst, particularly dibutyltin dilaurate, can facilitate the production of the desired final product.

Reaction can be monitored by infrared spectroscopy, by monitoring the disappearance of between 2300 cm ^-1 from the characteristic peak 2200 cm ^-1 of the isocyanate. At the end of the reaction, ethanol can be added to the reaction medium to neutralize any residual isocyanate functionality. The reaction mixture can optionally be filtered. The polymer can also be stripped directly in cosmetic solvents.

  According to one particular embodiment, the supramolecular polymer is dissolved in a hydrocarbon-based oil which is preferably volatile, in particular in isododecane.

  Thus, the composition according to the invention will comprise at least one hydrocarbon-based oil which is applied in particular by a supramolecular polymer solution, preferably volatile, in particular at least isododecane.

  More particularly, the composition for making up and / or caring for the lips, in particular the lips as defined above, comprises at least one supramolecular polymer, at least 0.1% by weight, based on its total weight, Preferably, it can be contained at least 1% by mass.

  In a variant of the embodiment of the composition according to the invention and the method, the supramolecular polymer is present in the composition according to the invention in an amount ranging from 0.1% to 60% by weight relative to the total weight of the composition. can do.

  Thus, supramolecular polymers can be present in the composition according to the invention in an amount ranging from 1% to 60% by weight relative to the total weight of the composition.

  Similarly, supramolecular polymers can be present in the composition according to the invention in an amount ranging from 2.5% to 50% by weight relative to the total weight of the composition.

  Supramolecular polymers can also be present in the composition according to the invention in an amount ranging from 4% to 40% by weight relative to the total weight of the composition.

  Advantageously, the composition according to the invention, in particular in the case of compositions for making up the skin and / or lips, is a supramolecular polymer relative to the weight of the composition excluding volatile compounds (specifically In a content of between 2.5% and 90% by weight (based on the weight of the composition excluding volatile oils such as isododecane).

  This content is produced, for example, after evaporation of volatile compounds, in particular on keratin materials, in particular on the skin and / or lips, in the deposits made with the composition according to the invention or by the method according to the invention. It reflects the content of the supramolecular polymer.

  Preferably, the composition according to the invention, especially in the case of makeup compositions, contains supramolecular polymers between 3% and 80% by weight, preferably 5% by weight with respect to the weight of the composition excluding volatile compounds. Containing at a content between% and 50% by weight.

Nonvolatile silicone oil The composition according to the invention comprises at least one non-volatile silicone oil.

  The term “oil” means a non-aqueous compound that is immiscible with water and is liquid at room temperature (25 ° C.) and atmospheric pressure (760 mmHg).

  Silicone oils that can be used in accordance with the present invention are non-volatile.

  In particular, the non-volatile silicone oil that can be used in the present invention has a viscosity at 25 ° C. of 9 to 800,000 cSt, preferably 600,000 cSt or less, and preferably 500,000 cSt or less. The viscosity of these silicone oils can be measured according to ASTM standard D-445.

The term “non-volatile oil” refers to an oil whose vapor pressure at room temperature and atmospheric pressure is non-zero, less than 0.02 mmHg (2.66 Pa), and better still less than 10 ⁻³ mmHg (0.13 Pa). means.

In particular, the non-volatile silicone oil that can be used in the present invention has a viscosity of at least 9 centistokes (cSt) (9 × 10 ⁻⁶ m ² / s) at 25 ° C., preferably less than 800,000 cSt, preferably from 50 It may be selected from silicone oils that are between 600000 cSt, preferably between 100 and 500000 cSt. The viscosity of the silicone oil can be measured according to ASTM standard D-445.

  Among these silicone oils, a distinction can be made between two types of oils depending on whether they contain phenyl or not.

1. Non-phenylated non-volatile silicone oil According to the first embodiment, the non-volatile silicone oil is a non-phenylated silicone oil.

  The expression “non-phenylated silicone oil” or “non-phenyl silicone oil” means a silicone oil having no phenyl substituent.

  Representative examples of these non-volatile non-phenylated silicone oils that may be mentioned include polydimethylsiloxane; alkyl dimethicone; vinyl methyl methicone; and optionally modified with fluorinated aliphatic groups, There are also silicones modified with functional groups such as hydroxyl groups, thiol groups and / or amine groups.

  According to a first embodiment, the non-volatile silicone oil is a non-phenylated oil, preferably modified with polydimethylsiloxane; alkyl dimethicone; vinyl methyl methicone; and optionally with an fluorinated aliphatic group. Selected or modified with functional groups such as hydroxyl, thiol and / or amine groups.

  The non-volatile non-phenylated silicone oil is preferably selected from dimethicone oils, preferably selected from polydimethylsiloxane, alkyl dimethicone.

  “Dimethicone” (INCL name) corresponds to polydimethylsiloxane (chemical name).

The non-phenylated non-volatile silicone oil can be selected from:
-Non-volatile polydimethylsiloxane (PDMS),
-PDMS which is pendant and / or at the end of the silicone chain and in which these groups contain alkyl or alkoxy groups each having from 2 to 24 carbon atoms, eg commercial reference names from Evonik Goldschmidt Cetyl dimethicone, sold in ABIL WAX9801
-PDMS containing aliphatic and / or aromatic groups or functional groups such as hydroxyl groups, thiol groups and / or amine groups,
A polyalkylmethylsiloxane, for example cetyl dimethicone sold under the commercial reference name ABIL WAX9801 from the company Evonik Goldschmidt, or a polyalkylmethylsiloxane optionally substituted with a fluorinated group, for example polymethyltrifluoropropyldimethylsiloxane,
-Polyalkylmethylsiloxanes substituted with functional groups such as hydroxyl groups, thiol groups and / or amine groups,
-Polysiloxanes modified with fatty acids, fatty alcohols or polyoxyalkylenes, and mixtures thereof.

  According to one embodiment, the composition according to the invention contains at least one non-phenylated linear silicone oil.

  These non-volatile non-phenylated linear silicone oils include polydimethylsiloxane; alkyl dimethicone; vinyl methyl methicone; and optionally modified with fluorinated aliphatic groups, or hydroxyl groups, thiol groups and / or It may be selected from silicones modified with functional groups such as amine groups.

  The non-phenylated linear silicone oil may in particular be selected from silicones of the following formula (I)

(Where
R ₁ , R ₂ , R ₅ and R ₆ together or separately are alkyl groups having 1 to 6 carbon atoms;
R ₃ and R ₄ together or separately are alkyl groups having 1 to 6 carbon atoms, vinyl groups, amine groups or hydroxyl groups;
X is an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or an amine group,
n and p are integers chosen in particular to have a liquid compound whose viscosity at 25 ° C. is between 9 centistokes (cSt) (9 × 10 ⁻⁶ m ² / s) and 800,000 cSt ).

Nonvolatile non-phenylated silicone oils that can be used according to the present invention can include the following:
-Substituents R _{1 to} R ₆ and X are methyl groups, p and n are numbers such that the viscosity is 500,000 cSt, for example the product sold under the name SE30 by General Electric, the name by Wacker Products sold under the name AK 500,000, products sold under the name Mirasil DM 500000 from Bluestar and products sold under the name Dow Corning200 Fluid500000cSt by Dow Corning,
The substituents R _{1 to} R ₆ and X represent methyl groups, and p and n are numbers such that the viscosity is 60000 cSt, for example the product sold under the name Dow Corning 200 Fluid 60000CS by the company Dow Corning, and Product sold under the name Wacker Belsil DM60000 by Wacker,
-The substituents R _{1 to} R ₆ and X represent a methyl group, and p and n are numbers such that the viscosity is 350 cSt, for example the product sold under the name Dow Corning 200 Fluid 350CS by the company Dow Corning,
-The substituents R ₁ to R ₆ represent a methyl group, the X group represents a hydroxyl group, and n and p are numbers such that the viscosity is 700 cSt, for example sold under the name Baysilone Fluid T0.7 by Momentive Product.

  According to one particular embodiment, the composition comprises a polyalkylmethylsiloxane, for example cetyl dimethicone sold under the commercial reference ABIL WAX9801 from the company Evonik Goldschmidt. Preferably, the composition comprises 0.1-10% polyalkylmethylsiloxane, such as cetyl dimethicone.

2. Nonvolatile phenylated silicone oil According to a variant of the second preferred embodiment, the composition according to the invention contains at least one nonvolatile phenylated silicone oil.

  The expression “phenylated silicone oil” or “phenyl silicone oil” means a silicone oil having at least one phenyl substituent.

The non-volatile phenylated silicone oil is selected from:
a) Phenyl silicone oil corresponding to the following formula (I)

(Wherein the R groups independently of one another represent methyl or phenyl, provided that at least one R group represents phenyl). Preferably, in this formula, the phenyl silicone oil comprises at least 3 phenyl groups, for example at least 4, at least 5 or at least 6 phenyl groups.
b) Phenyl silicone oil corresponding to the following formula (II)

(Wherein the R groups independently of one another represent methyl or phenyl, provided that at least one R group represents phenyl). Preferably, in this formula, the organopolysiloxane comprises at least 3 phenyl groups, such as at least 4 or at least 5 phenyl groups. Mixtures of the aforementioned phenylorganopolysiloxanes can be used. Examples that may be mentioned are mixtures of triphenyl, tetraphenyl or pentaphenylorganopolysiloxane.
c) Phenyl silicone oil corresponding to the following formula (III)

(Wherein Me represents methyl and Ph represents phenyl).

Such phenyl silicone oil is preferably trimethylpentaphenyltrisiloxane or tetramethyltetraphenyltrisiloxane. These oils are specifically referred to by Dow Corning under the reference name PH-1555HRI or Dow Corning555 Cosmetic Fluid (chemical name: 1,3,5-trimethyl-1,1,3,5,5-pentaphenyltrisiloxane; INCI name: trimethyl Tetramethyltetraphenyltrisiloxane, manufactured by Pentaphenyltrisiloxane) or sold by Dow Corning under the reference Dow Corning554 Cosmetic Fluid may also be used.
d) Phenyl silicone oil corresponding to the following formula (IV)

[Wherein Me represents methyl, y is between 1 and 1000, and X represents —CH ₂ —CH (CH ₃ ) (Ph)].
e) Phenyl silicone oil corresponding to the following formula (V)

(Wherein Me is methyl, Ph is phenyl, OR ′ represents an —OSiMe ₃ group, y is 0, or ranges between 1 and 1000, and z is 1 to 1000. The range between). Specifically, y and z are numbers such that compound (V) is a non-volatile oil.

  According to the first embodiment, y ranges between 1 and 1000. Usable are, for example, trimethylsiloxyphenyl dimethicone sold in particular under the reference name Belsil PDM1000 by the company Wacker.

According to the second embodiment, y is equal to 0. Usable are, for example, phenyltrimethylsiloxytrisiloxanes sold in particular under the reference name Dow Corning 556 Cosmetic Grade Fluid (DC556).
f) Phenyl silicone oils corresponding to the following formula (VI), and mixtures thereof

[Where
R ₁ to R ₁₀ are, independently of one another, saturated or unsaturated, linear, cyclic or branched C _{1 to} C ₃₀ hydrocarbon-based groups;
-m, n, p and q are independently integers between 0 and 900, provided that the sum m + n + q is not 0).

  Preferably, the sum m + n + q is between 1 and 100. Preferably, the sum m + n + p + q is between 1 and 900, better still between 1 and 800. Preferably q is equal to 0.

Preferably, R ₁ to R ₁₀ independently of one another represent a saturated or unsaturated, linear or cyclic C _{1 to} C ₃₀ hydrocarbon group, preferably saturated, in particular C _{1 to} C ₁₂ carbonization. a hydrogen-based group, C ₃ -C ₁₆ with particular, and more particularly C ₄ -C _10, or a monocyclic or polycyclic C ₆ -C ₁₄ and in particular C ₁₀ -C ₁₃ aryl group, or aralkyl group is there. Preferably, R ₁ to R ₁₀ can each represent a methyl, ethyl, propyl, butyl, isopropyl, decyl, dodecyl or octadecyl group, or alternatively a phenyl, tolyl, benzyl or phenethyl group. R ₁ to R ₁₀ may in particular be the same and can further be a methyl group
g) Phenyl silicone oil corresponding to the following formula (VII) and mixtures thereof

(Where
R ₁ to R ₆ are, independently of one another, saturated or unsaturated, linear, cyclic or branched C _{1 to} C ₃₀ hydrocarbon-based groups, preferably R ₁ to R ₆ are C 1 ₁ -C ₃₀ alkyl group, an aryl group or an aralkyl group,
-m, n and p are, independently of one another, an integer between 0 and 100, provided that the sum n + m is between 1 and 100).

Preferably, R ₁ to R ₆ are, independently of one another, a saturated or unsaturated, linear or branched C ₁ -C ₃₀ hydrocarbon group, preferably saturated, in particular C ₁ -C ₁₂ is a hydrocarbon group, specifically from _{C 3 ~C 16, C 4 ~C} 10 and more particularly, or a monocyclic or polycyclic C ₆ -C ₁₄ and in particular C ₁₀ -C ₁₃ aryl group, or aralkyl It is a group. Preferably, R ₁ to R ₆ can each represent a methyl, ethyl, propyl, butyl, isopropyl, decyl, dodecyl or octadecyl group, or alternatively a phenyl, tolyl, benzyl or phenethyl group.

R ₁ to R ₆ may be particularly the same or may be a methyl group. Preferably, in formula (VII), m = 1 or 2 or 3 and / or n = 0 and / or p = 0 or 1 may be applied.
h) Phenyl silicone oil corresponding to the following formula, and mixtures thereof

(Where
R ₁ , R ₂ , R ₅ and R ₆ are alkyl groups having 1 to 6 carbon atoms together or separately, and R ₃ and R ₄ are 1 to 6 together or separately. An alkyl group having a carbon atom, or an aryl group, provided that at least one of R ₃ and R ₄ is a phenyl group,
X is an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a vinyl group,
n and p are integers greater than or equal to 1 selected to give the oil a weight average molecular weight of less than 200,000 g / mol, preferably less than 150,000 g / mol, more preferably less than 100,000 g / mol)
i) as well as mixtures thereof.

Examples of preferred non-volatile silicone oils that may be mentioned include, for example, the following silicone oils:
A phenyl silicone oil, preferably selected from: tetramethyltetraphenyltrisiloxane (e.g. PH-1554 HRI or Dow Corning 554 Cosmetic Fluid from Dow Corning), trimethylsiloxyphenyl dimethicone (e.g. Belsil PDM1000 {from Wacker) See formula (V) above}], phenyltrimethicone (eg phenyltrimethicone sold under the trademark DC556 by Dow Corning), phenyldimethicone, phenyltrimethylsiloxydiphenylsiloxane, diphenyldimethicone [eg Shin-Etsu Chemical KF-54 (400cSt) from Shin-Etsu Chemical Co., Ltd.KF54HV (5000cSt) from Shin-Etsu Chemical Co., Ltd., KF-50-300CS (300cSt) from Shin-Etsu Chemical Co., Ltd., KF-53 from Shin-Etsu Chemical Co., Ltd. 175 cSt), KF-50-100CS (100 cSt) from Shin-Etsu Chemical Co., Ltd.], diphenylmethyldiphenyltrisiloxane, 2-phenyl ester Rutrimethylsiloxysilicate, trimethylpentaphenyltrisiloxane [eg the product sold under the name Dow Corning PH-1555 HRI Cosmetic Fluid by the company Dow Corning (see formula (III) above)], diphenylsiloxyphenyltrimethicone (For example, KF56A from Shin-Etsu Chemical Co., Ltd.)
Non-volatile polydimethylsiloxane (PDMS), a polydimethylsiloxane that is pendant and / or at the end of a silicone chain, each group containing an alkyl or alkoxy group with 2 to 24 carbon atoms,
-And mixtures thereof.

The phenyl silicone is more preferably selected from:
-Phenyltrimethicone,
-Tetramethyltetraphenyltrisiloxane
-Diphenylsiloxyphenyl trimethicone,
-Diphenylsiloxyphenyl dimethicone,
-Trimethylpentaphenyltrisiloxane,
-Phenyl dimethicone,
-Phenyltrimethylsiloxydiphenylsiloxane,
-Diphenyl dimethicone,
-Diphenylmethyldiphenyltrisiloxane, and
-2-phenylethyltrimethylsiloxysilicate,
-As well as mixtures thereof.

More specifically, the phenyl silicone is selected from:
-Phenyltrimethicone,
-Diphenylsiloxyphenyl trimethicone,
-Diphenylsiloxyphenyl dimethicone,
-Phenyl dimethicone,
-Phenyltrimethylsiloxydiphenylsiloxane,
-Diphenyl dimethicone,
-Diphenylmethyldiphenyltrisiloxane, and
-2-phenylethyltrimethylsiloxysilicate,
-As well as mixtures thereof.

  Preferably, the mass average molecular weight of the non-volatile phenyl silicone oil according to the present invention ranges from 500 to 10000 g / mol.

Nonvolatile phenyl silicone oil having at least a dimethicone moiety According to a first preferred embodiment, the nonvolatile phenylated silicone oil is selected from phenyl dimethicone oil (which means a phenyl silicone oil having at least a dimethicone moiety). The Preferably, the non-volatile silicone oil is selected from oils corresponding to formula (VII):

(Wherein R ₁ to R ₆ , m, n and p are as defined above).
A) According to the first embodiment, in formula (VII), m = 0, and n and p are independently an integer between 1 and 100. Preferably, R ₁ to R ₆ are methyl groups. According to this embodiment, the silicone oil is preferably selected from diphenyl dimethicone, such as KF-54 (400 cSt) from Shin-Etsu Chemical Co., Ltd., KF54HV (5000 cSt) from Shin-Etsu Chemical Co., Ltd., Shin-Etsu Chemical Co., Ltd. KF-50-300CS (300cSt) from the company, KF-53 (175cSt) from Shin-Etsu Chemical Co., Ltd., and KF-50-100CS (100cSt) from Shin-Etsu Chemical Co., Ltd.
B) According to the second embodiment, in formula (VII), p is between 1 and 100, in formula (VII) the sum n + m is between 1 and 100 and n = 0 It is. Silicone oil selected from trimethylsiloxyphenyl dimethicone such as Belsil PDM1000 from Wacker is used as the silicone oil of formula (VII) (where n = 0 and R ₁ to R ₆ are methyl groups) It is particularly possible to do.

According to a first preferred embodiment, the silicone oil is a phenyl silicone oil having at least a dimethicone moiety, preferably selected from:
-Diphenyl dimethicone, for example KF-54 (400cSt) from Shin-Etsu Chemical Co., Ltd., KF54HV (5000cSt) from Shin-Etsu Chemical Co., Ltd., KF-50-300CS (300cSt) from Shin-Etsu Chemical Co., Ltd., Shin-Etsu Chemical Co., Ltd. KF-53 (175cSt) from Co., Ltd., KF-50-100CS (100cSt) from Shin-Etsu Chemical Co., Ltd.,
-Trimethylsiloxyphenyl dimethicone, for example Belsil PDM1000 from Wacker, trimethylsiloxyphenyl trimethicone,
-Trimethylpentaphenyltrisiloxane, such as PH-1555 HRI or Dow Corning 555 Cosmetic Fluid from Dow Corning,
-And mixtures thereof.

Nonvolatile Phenyl Silicone Oil Without Dimethicone Part According to a second embodiment, the silicone oil is a phenyl silicone oil without a dimethicone part.

Nonvolatile phenylated silicone oils that do not have a dimethicone moiety may be selected from:
a) Phenyl silicone oil corresponding to the following formula (I)

(Wherein the R groups independently of one another represent methyl or phenyl, provided that at least one R group represents phenyl. Preferably, in this formula, the phenyl silicone oil comprises at least three phenyl groups, such as at least 4, including at least 5 or at least 6),
b) Phenyl silicone oil corresponding to the following formula (II)

(Wherein the R groups independently of one another represent methyl or phenyl, provided that at least one R group represents phenyl. Preferably, in this formula, the organopolysiloxane comprises at least three phenyl groups, for example Examples of which may be mentioned include mixtures of triphenyl, tetraphenyl or pentaphenylorganopolysiloxanes, which may include mixtures of phenylorganopolysiloxanes as described above). ,
c) Phenyl silicone oil corresponding to the following formula (III)

(Wherein Me represents methyl and Ph represents phenyl).
Such phenyl silicones, in particular by Dow Corning, have the reference name PH-1555 HRI or Dow Corning 555 Cosmetic Fluid (chemical name: 1,3,5-trimethyl-1,1,3,5,5-pentaphenyltrisiloxane). Tetramethyltetraphenyltrisiloxane, manufactured under the name Dow Corning 554 Cosmetic Fluid, manufactured by Dow Corning, Inc. can also be used;
d) Phenyl silicone oil corresponding to the following formula (V ')

[Wherein Me is methyl, Ph is phenyl, OR ′ represents —OSiMe ₃ group, y is 0, z ranges between 1 and 1000, and in particular z is a compound It is a number such that (V ′) is a non-volatile oil].

According to the second embodiment, y is equal to 0. Usable are, for example, phenyltrimethylsiloxytrisiloxanes sold in particular under the reference name Dow Corning556 Cosmetic Grade Fluid (DC556).
e) Phenyl silicone oil corresponding to the following formula (VIII) and mixtures thereof

(Where
- R independently of one another, saturated or unsaturated, linear, cyclic or branched C ₁ -C ₃₀ hydrocarbon-based group, preferably R is C ₁ -C ₃₀ alkyl group, an aryl Group or aralkyl group,
-m and n are, independently of one another, an integer between 0 and 100, provided that the sum n + m is between 1 and 100).

Preferably, R, independently of one another, is a saturated or unsaturated, linear or branched C _{1 to} C ₃₀ hydrocarbon group, preferably saturated, in particular a C _{1 to} C ₁₂ hydrocarbon group. More specifically C ₃ -C ₁₆ , more particularly C ₄ -C ₁₀ , or monocyclic or polycyclic C ₆ -C ₁₄ and especially C ₁₀ -C ₁₃ aryl groups, or aralkyl groups. Preferably, R may each represent a methyl, ethyl, propyl, butyl, isopropyl, decyl, dodecyl or octadecyl group, or alternatively a phenyl, tolyl, benzyl or phenethyl group. R may be particularly the same or may be a methyl group. Preferably, in formula (VIII), m = 1, 2 or 3, and / or n = 0.

  According to one preferred embodiment, in formula (VIII), n is an integer between 0 and 100 and m is an integer between 1 and 100, provided that the sum n + m is from 1 to 100. Between 100. Preferably, R is a methyl group.

According to one embodiment, the viscosity at 25 ° C. is between 5 and 1500 mm ² / s (ie 5 to 1500 cSt), preferably the viscosity is between 5 and 1000 mm ² / s (ie 5 to 1000 cSt). A phenyl silicone oil of formula (VIII) can be used.

  According to this embodiment, the non-volatile phenyl silicone oil is preferably selected from phenyl trimethicone, such as DC556 (22.5 cSt) from Dow Corning, KF56A from Shin-Etsu Chemical Co., Ltd., oil diphenylsiloxyphenyl tri Methicone, Oil Silbione 70663V30 (28cSt) from Rhone-Poulenc. The value in parenthesis represents the viscosity at 25 ° C.

According to this embodiment, when n = 0, the silicone oil is preferably DC556 from Dow Corning, and when m and n are between 1 and 100, the silicone oil is preferably Shin-Etsu. KF56A from Chemical Industry Co., Ltd.
f) and mixtures thereof.

Preferably, the non-volatile phenylated silicone oil having no dimethicone moiety may be selected from:
-Phenyltrimesylsiloxytrisiloxane, phenyltrimethicone, eg DC556 from Dow Corning,
-Tetramethyltetraphenyltrisiloxane, such as PH-1554HRI or Dow Corning554 Cosmetic Fluid from Dow Corning,
-Diphenylsiloxyphenyl trimethicone, for example KF56A from Shin-Etsu Chemical Co., Ltd., Oil Silbione 70663V30 from Rhone-Poulenc,
-Trimethylpentaphenyltrisiloxane, such as PH-1555HRI or Dow Corning555 Cosmetic Fluid from Dow Corning,
-And mixtures thereof.

  Preferably, the composition according to the invention advantageously contains a non-volatile silicone in a total of 1% to 80%, in particular 2% to 70%, preferably 5%, based on the total weight of the composition. Contains from 60% to 60% by weight.

  Of the silicone oils mentioned above, it should be noted that phenyl silicone oil has been found to be particularly advantageous. They can in particular give a good level of gloss to deposits made on the skin or lips with the composition according to the invention without causing any sticking, and non-volatile hydrocarbonation. With oil, it allows the formation of deposits that do not transfer color.

  In particular, a composition according to the invention for caring for and / or making up the lips, more specifically a lipstick or lip gloss type, comprises a non-volatile silicone oil according to the invention as a total of the composition. It can be contained in an amount of 1% by mass to 80% by mass relative to the mass.

  Advantageously, the composition according to the invention for caring for and / or making up the lips, more particularly of the lipstick or lip gloss type, comprises a non-volatile silicone oil according to the invention as a total of the composition. 5 mass% to 60 mass% can be included with respect to the mass.

  Advantageously, the composition according to the invention for caring for and / or making up the lips, more particularly of the lipstick or lip gloss type, comprises a non-volatile silicone oil according to the invention as a total of the composition. It can be contained in an amount of 10% by mass to 50% by mass with respect to the mass.

  According to one particular embodiment, in particular in the case of a lip makeup composition, it can comprise more than 10% by weight of the silicone compound according to the invention relative to the total weight of the composition.

Nonvolatile Hydrocarbonized Oil The composition according to the invention comprises at least one non-volatile hydrocarbonated oil (also called “hydrocarbon-based” oil).

Nonpolar Oil According to the first embodiment, the non-volatile hydrocarbon oil may be a nonpolar oil.

For the purposes of the present invention, the term “apolar oil” means an oil with a solubility parameter at 25 ° C., δ _a equal to 0 (J / cm ³ ) ^1/2 .

  The definition and calculation of solubility parameters in Hansen 3D solubility space is described in the article “The three dimensional solubility parameters” by C.M. Hansen, J. Paint Technol., 39, 105 (1967).

According to this Hansen space,
-δ _D is characterized by the London dispersion force resulting from the formation of dipoles induced during molecular collisions,
-δ _p is characterized by the Debye interaction force between the permanent dipoles and the Caesom interaction force between the induced and permanent dipoles,
- [delta] _h is characterized by specific interaction forces (e.g. hydrogen bonding, acid / base, donor / acceptor, etc.), and
-δ _a is determined by the equation: δ _a = (δ _p ² + δ _h ² ) ^1/2 .

The parameters δ _p , δ _h , δ _D and δ _a are represented by (J / cm ³ ) ^1/2 .

  The term “hydrocarbon-based oil” (or “hydrocarbonized oil” or “hydrocarbon oil”) is formed essentially from or further by carbon and hydrogen atoms, and optionally oxygen and nitrogen atoms. It means an oil that is composed and does not contain any silicon or fluorine atoms. This may contain alcohol groups, ester groups, ether groups, carboxylic acid groups, amine groups and / or amide groups.

  These oils can be of plant origin, mineral origin or synthetic origin.

  Preferably, the non-volatile nonpolar hydrocarbon-based oil may be selected from linear or branched hydrocarbons of mineral or synthetic origin.

Specifically, the non-volatile nonpolar hydrocarbon-based oil is selected from the following:
-Liquid paraffin or its derivatives,
-Squalane,
-Isoeikosan,
-Naphthalene oil,
-Polybutylene, such as Indopol H-100 (molar mass or MW = 965 g / mol), Indopol H-300 (MW = 134 g / mol) and Indopol H-1500 (MW = 2160 g / mol, manufactured or sold by Amoco ),
-Polyisobutene,
-Hydrogenated polyisobutylene, for example Parleam (registered trademark) sold by NOF Corporation, Panalane H-300E (MW = 1340 g / mol) manufactured or sold by Amoco, manufactured or sold by Synteal Viseal 20000 (MW = 6000 g / mol) and Rewopal PIB1000 (MW = 1000 g / mol) manufactured or sold by Witco, or Parleam Lite sold by NOF Corporation instead,
-Decene / butene copolymer, polybutene / polyisobutene copolymer, especially Indopol L-14,
-Polydecene and hydrogenated polydecene, e.g. Puresyn 10 (MW = 723 g / mol) and Puresyn 150 (MW = 9200 g / mol) manufactured or sold by Mobil Chemicals, or alternatively Puresyn 6, sold by ExxonMobil Chemical,
-As well as mixtures thereof.

  Preferably, the composition according to the invention comprises at least one non-volatile hydrocarbonaceous apolar oil, which is preferably polybutene, polyisobutene, hydrogenated polyisobutene, polydecene and / or hydrogenated polydecene, and mixtures thereof. Selected from.

  The composition according to the invention comprises a non-volatile hydrocarbon oil in an amount of 1% to 80% by weight, for example 2% to 70% by weight, preferably 5% to 60% by weight, based on the total weight of the composition. It can be included in a range of contents.

  Preferably, the non-volatile hydrocarbon oil is at least one nonpolar oil, preferably ranging from 1% to 80% by weight, preferably from 2% to 70% by weight, based on the total weight of the composition. It is included in the content.

  Preferably, the non-volatile hydrocarbon oil comprises at least one nonpolar oil, preferably 5% to 60% by weight, preferably 10% to 50% by weight, based on the total weight of the composition. Including content in the range.

Polar oil According to the second embodiment, the non-volatile hydrocarbon oil may be a polar hydrocarbon oil.

For the purposes of the present invention, the term “polar oil” means an oil whose solubility parameter δ _a at 25 ° C. is not 0 (J / cm ³ ) ^1/2 .

  These oils can be of plant origin, mineral origin or synthetic origin.

In particular, the hydrocarbon-based non-volatile polar oil may be selected from the following list of oils and mixtures thereof:
Hydrocarbon hydrocarbon oils, such as liquid triglycerides of fatty acids having 4 to 10 carbon atoms, such as heptanoic acid or octanoic acid triglycerides, or jojoba oil,
-Ester oil, preferably selected from:
-Fatty acid esters, in particular those of 4 to 22 carbon atoms, in particular those of octanoic acid, heptanoic acid, lanolinic acid, oleic acid, lauric acid or stearic acid, such as propylene glycol dioctanoate, propylene glycol monoisostearate Or neopentyl glycol diheptanoate,
Synthetic esters, for example the formula R ₁ COOR ₂ , wherein R ₁ represents a linear or branched fatty acid residue having 4 to 40 carbon atoms, R ₂ represents 4 to 40 carbon atoms, a hydrocarbon-based chain is particularly branched, however, the oil of R ₁ + a R ₂ ≧ 16), for example, purcellin oil (cetostearyl octanoate), isononyl isononanoate, C ₁₂ ~ C ₁₅ alkyl benzoate, 2-ethylhexyl palmitate, octyldodecyl neopentanoate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, oleyl erucate, isostearyl isostearate, 2-octyldodecyl benzoate, octanoic acid, Decanoic acid or ricinoleic alcohol or polyalcohol, isopropyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, 2-ethyl palmitate Hexyl, 2-hexyldecyl laurate, palmitate 2-octyl-decyl, 2-diethylhexyl 2-octyldodecyl myristate or succinic acid; preferably, preferred synthetic esters R ₁ COOR ₂ (wherein, R ₁ is 4 Represents a straight-chain or branched fatty acid residue having 40 carbon atoms, R ₂ represents a hydrocarbon-based chain having 4 to 40 carbon atoms, in particular branched, provided that R ₁ + R ₂ ≧ 20),
-Linear fatty acid esters with a total carbon number ranging from 35 to 70, for example pentaerythrityl tetrapelargonate (MW = 697 g / mol),
-Hydroxylated esters, preferably those having a total carbon number in the range 35-70, such as polyglyceryl-2 triisostearate (MW = 965 g / mol), isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, malein Diisostearyl acid, glyceryl stearate; diethylene glycol diisononanoate,
-Esters of aromatic acids with alcohols having 4 to 22 carbon atoms, for example tridecyl trimellitate (MW = 757 g / mol),
- branched C ₂₄ -C ₂₈ esters of fatty alcohols or fatty acids such as those described in European Patent No. A-0955039, in particular citric acid Torii SOARER Kizil (MW = 1033.76g / mol), tetra isononanaldehyde acid Pentaerisu Lithyl (MW = 697 g / mol), glyceryl triisostearate (MM = 891 g / mol), glyceryl tris (2-decyl) tetradecanoate (MW = 1143 g / mol), pentaerythrityl tetraisostearate (MW = 1202 g / mol) ), Polyglyceryl tetraisostearate-2 (MW = 1232 g / mol) or tetrakis (2-decyl) tetradecanoic acid pentaerythrityl (MW = 1538 g / mol),
An optionally unsaturated polyester obtained by esterifying at least one hydroxylated carboxylic acid triglyceride with an aliphatic monocarboxylic acid and an aliphatic dicarboxylic acid, for example sold under the reference Zenigloss from Zenitech. Succinic acid and isostearic acid castor oil,
-Diol dimer and general formula HO-R ¹ -(-OCO-R ² -COO-R ^1- ) _h -OH
(Where
R ¹ represents a diol dimer residue obtained by hydrogenation of dilinoleic acid diacid,
R ² represents a hydrocarbonated dilinoleic acid diacid residue, and
h represents an integer ranging from 1 to 9)
Ester of diacid dimer,
In particular, an ester of dilinoleic acid diacid and dilinoleyldiol dimer sold under the trade name Lusplan DD-DA5 (registered trademark) and DD-DA7 (registered trademark) by Nippon Fine Chemical Co., Ltd.
Polyesters obtained by condensation of unsaturated fatty acid timers and / or trimers and diols, such as those described in French Patent 0853634, in particular polyesters obtained by condensation of dilinoleic acid and 1,4-butanediol. Mention may be made in this regard of polymers sold under the name Viscoplast 14436H by the company Biosynthis (INCI name: dilinoleic acid / butanediol copolymer), or copolymers of polyols and diacid dimers, and their esters, for example Hailuscent. ISDA,
A fatty alcohol having 12 to 26 carbon atoms, preferably branched, such as octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol and oleyl alcohol;
- C ₁₂ -C ₂₂ higher fatty acids such as oleic acid, linoleic acid and linolenic acid, and mixtures thereof,
-Oils of plant origin, such as sesame oil (820.6 g / mol),
-Fatty acids having 12 to 26 carbon atoms, such as oleic acid,
A dialkyl carbonate in which the two alkyl chains are probably identical or different, for example dicaprylyl carbonate sold under the name Cetiol CC® by the company Cognis,
-Vinylpyrrolidone copolymers such as vinylpyrrolidone / 1-hexadecene copolymer, Antaron V-216 (MW = 7300 g / mol) manufactured or sold by ISP.

Preferably, the composition according to the invention comprises at least one non-volatile hydrocarbon oil selected from:
-Vinylpyrrolidone copolymers, preferably for example vinylpyrrolidone / 1-hexadecene copolymer,
-Hydroxylated esters, preferably in the range 35-70 total carbons, polyglyceryl-2 triisostearate, isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl maleate, glyceryl stearate; Preferably selected from diethylene glycol diisononanoate,
-Oils from plant sources, preferably selected from liquid triglycerides of fatty acids,
-Triisoarachidyl citrate (MW = 1033.76 g / mol), pentaerythrityl tetraisononanoate (MW = 697 g / mol), glyceryl triisostearate (MM = 891 g / mol), glyceryl tris (2-decyl) tetradecanoate (MW = 1143 g / mol), pentaerythrityl tetraisostearate (MW = 1202 g / mol), polyglyceryl tetraisostearate-2 (MW = 1232 g / mol) or tetrakis (2-decyl) tetradecanoic acid pentaerythrityl (MW = Branched fatty alcohols or fatty acid C ₂₄ -C ₂₈ esters, preferably selected from 1538 g / mol),
-Formula R ₁ COOR _{2 wherein} R ₁ represents a linear or branched fatty acid residue having 4 to 40 carbon atoms and R ₂ has 4 to 40 carbon atoms In particular a branched hydrocarbon-based chain, provided that R ₁ + R ₂ ≧ 16)
-And mixtures thereof.

  Preferably, the non-volatile hydrocarbon oil is at least one polar oil, preferably ranging from 1% to 80% by weight, preferably from 2% to 70% by weight, based on the total weight of the composition. It is included in the content.

  Preferably, the non-volatile hydrocarbon oil ranges from at least one polar oil, preferably 5% to 60% by weight, preferably 10% to 50% by weight, based on the total weight of the composition. It is included in the content.

  Preferably, the mass ratio of total non-volatile hydrocarbonated oil to total non-volatile silicone oil is between 0.1 and 10, more preferably between 0.1 and 5, preferably between 0.5 and 5.

  Preferably, the mass ratio of the total nonpolar non-volatile hydrocarbonated oil to the total non-volatile silicone oil is between 0.1 and 10, preferably between 0.1 and 5.

  Preferably, the mass ratio of the total nonpolar non-volatile hydrocarbonated oil to the total non-volatile phenyl silicone oil is between 0.1 and 10, more preferably between 0.1 and 5.

  The makeup and / or care cosmetic compositions of the present invention also include a cosmetically acceptable medium that may include conventional ingredients as a function of the intended use of the composition.

  The composition also comprises at least one additional compound, preferably selected from hydrocarbonated polar oils and / or fatty pasty compounds and / or fillers, and / or colorants, and / or mixtures thereof. be able to.

Additional Fat Phase According to one embodiment, the composition according to the invention may comprise an additional liquid fatty phase in addition to the non-volatile silicone oil and the non-volatile hydrocarbonated oil.

  The additional liquid fatty phase can represent from 0.1% to 98% by weight relative to the total weight of the composition.

  It is understood that this weight percent of the liquid fatty phase takes into account the weight of oil used for the formulation of the accompanying supramolecular polymer (if present).

  In particular, the composition according to the invention and / or the composition used in the composition according to the invention may comprise from 0.1% to 95% by weight of an additional liquid fatty phase relative to the total weight of the composition. it can.

  More particularly, the composition according to the invention and / or the composition used in the composition according to the invention comprises from 0.5% to 90% by weight of an additional liquid fatty phase relative to the total weight of the composition. Can do.

Volatile oil According to a preferred embodiment, the composition according to the invention may comprise a volatile oil.

  Thus, the composition under investigation according to the invention may advantageously comprise one or more oils that may be specifically selected from volatile hydrocarbon-based oils, volatile silicone oils and fluoro oils, and mixtures thereof. .

For the purposes of the present invention, the term “volatile oil” means an oil that can evaporate in less than one hour when contacted with keratin materials at room temperature (25 ° C.) and atmospheric pressure (760 mmHg). Volatile oil is a cosmetic volatile oil, which is liquid at room temperature, in particular, the vapor pressure ranges from 0.13 Pa to 40,000 Pa (10 ^{−3 to} 300 mmHg), preferably from 1.3 Pa. The range is 13000 Pa (0.01 to 100 mmHg), preferentially 1.3 Pa to 1300 Pa (0.01 to 10 mmHg).

  The oil can be of animal origin, plant origin, mineral origin or synthetic origin.

Volatile fluoro oil The term “fluoro oil” means an oil containing at least one fluorine atom.

  The fluoro oils that can be used in the present invention may be selected from fluorosilicone oils, fluoropolyethers and fluorosilicones described in EP-A-847752, and perfluoro compounds.

  According to the invention, the term “perfluoro compound” means a compound in which all hydrogen atoms are replaced by fluorine atoms.

  According to a preferred embodiment, the fluoro oil according to the invention is selected from perfluoro oils. Examples of perfluoro oils that can be used in the present invention are perfluorodecalin and perfluoroperhydrophenanthrene.

  According to one preferred embodiment, the fluoro oil is selected from perfluoroperhydrophenanthrene, specifically the Fiflow® product sold by the companies Creations Couleurs. In particular, it is possible to use a fluoro oil whose INCI name is perfluoroperhydrophenanthrene and sold under the reference name Fiflow220 by the company F2 Chemicals.

Volatile hydrocarbon oil According to a preferred embodiment, the composition according to the invention further comprises a volatile hydrocarbonated oil such as isododecane and / or isohexadecane.

  Such compounds are compatible with non-volatile hydrocarbonated oils and silicone oils and improve the spreadability during application and the transfer resistance of the deposit.

  The term “hydrocarbon-based oil” (or “hydrocarbonized oil” or “hydrocarbon oil”) is formed essentially from or further from carbon and hydrogen atoms, and optionally oxygen and nitrogen atoms. It means an oil that is composed and does not contain any silicon or fluorine atoms. It may contain alcohol groups, ester groups, ether groups, carboxylic acid groups, amine groups and / or amide groups.

Volatile hydrocarbon oils are hydrocarbon oils having 8 to 16 carbon atoms, especially branched C _{8 to} C ₁₆ alkanes (also known as isoparaffins), such as isododecane (2,2,4, 4,6-pentamethylheptane), isodecane and isohexadecane, and mixtures thereof.

  Volatile hydrocarbon-based oils are also linear volatile alkanes having 7 to 17 carbon atoms, specifically 9 to 15 carbon atoms, more specifically 11 to 13 carbon atoms. There may be. Particular mention may be made of n-nonadecane, n-decane, n-undecane, n-dodecane, n-tridecane, n-tetradecane, n-pentadecane and n-hexadecane, and mixtures thereof.

  The term “hydrocarbon-based oil” means an oil formed essentially from or further composed of carbon and hydrogen atoms, and optionally oxygen and nitrogen atoms, and containing no silicon or fluorine atoms. It is contemplated. It may contain alcohol groups, ester groups, ether groups, carboxylic acid groups, amine groups and / or amide groups.

  According to one embodiment, the composition according to the invention also comprises at least isodecane and / or isohexadecane.

  According to one embodiment, the composition does not contain additional volatile hydrocarbonated oils other than isodecane and / or isohexadecane.

  More particularly, the composition according to the invention contains between 1% and 60% by weight of volatile oil, preferably isodecane and / or isohexadecane, relative to its total weight.

  Preferably, the composition according to the invention contains between 2% and 50% by weight of volatile oil, preferably isodecane and / or isohexadecane, based on its total weight.

  Advantageously, the composition according to the invention contains between 5% and 40% by weight of volatile oil, preferably isodecane and / or isohexadecane, based on its total weight.

  Other volatile hydrocarbon-based solvents (oils) that can be used in the composition according to the invention include ketones that are liquid at room temperature, such as methyl ethyl ketone or acetone; short-chain esters (3-8 in total) E.g. ethyl acetate, methyl acetate, propyl acetate or n-butyl acetate; ethers which are liquid at room temperature, e.g. diethyl ether, dimethyl ether or dichlorodiethyl ether; alcohols and in particular 2 to 5 carbon atoms A linear or branched lower monoalcohol having the formula: for example ethanol, isopropanol or n-propanol.

  According to one preferred embodiment, the volatile oil has a flash point greater than 65 ° C, and better still greater than 80 ° C. An example of such a volatile oil is isohexadecane.

  Advantageously, the composition according to the invention comprises less than 5% by weight, more preferably less than 2% by weight, of volatile oils with a flash point of less than 80 ° C. Preferably, the composition according to the invention does not contain volatile oils with a flash point below 80 ° C.

Volatile Silicone Oil According to one embodiment, the composition according to the invention may comprise at least one volatile silicone oil.

  The term “silicone oil” is intended to mean an oil comprising at least one silicon atom, in particular comprising Si—O groups.

Volatile silicone oils that can be used in the present invention are specifically selected from silicone oils having a viscosity ≦ 8 centistokes (cSt) (8 × 10 ⁻⁶ m ² / s), preferably greater than 0.5 cSt. Can be done.

  The term “silicone oil” is intended to mean an oil comprising at least one silicon atom, in particular comprising Si—O groups.

  Volatile silicone oils that can be used in the present invention have a flash point in the range of 40 ° C. to 150 ° C., preferably a flash point of greater than 55 ° C. and less than or equal to 105 ° C. And selected from silicone oils. Specifically, the flash point is measured according to ISO standard 3679.

  Volatile silicone oils can be selected from linear or cyclic silicone oils, for example, linear or cyclic polydimethylsiloxanes (PDMS) having 3 to 7 silicon atoms.

  More specific mention may be made of volatile silicone oils, especially decamethylcyclopentasiloxane sold under the name DC-245 by the company Dow Corning, in particular dodeca sold under the name DC-246 by the company Dow Corning. Methylcyclohexasiloxane, especially octamethyltrisiloxane, polydimethylsiloxane sold under the name DC-200 Fluid 1cSt by Dow Corning, especially decamethyltetrasiloxane sold under the name DC-200 Fluid 1.5cSt by Dow Corning , And the name DC-200 Fluid 5cSt, sold by Dow Corning, octamethylcyclotetrasiloxane, heptamethylhexyltrisiloxane, heptamethylethyltrisiloxane, heptamethyloctyltrisiloxane and dodecamethyl from Shin-Etsu Chemical Co., Ltd. Pentasiloxane, Octyltrimethico , Hexyltrimethicone, decamethylcyclopentasiloxane (cyclopentasiloxa or D5), octamethylcyclotetrasiloxane (cyclotetradimethylsiloxane or D4), dodecamethylcyclohexasiloxane (D6), decamethyltetrasiloxane (L4) , KF96A, and mixtures thereof.

Solid fatty material The composition according to the invention may also preferably comprise at least one solid fatty material selected in particular from waxes and / or pasty fatty materials.

Wax According to the first embodiment, the composition does not contain a wax or contains less than 5% by weight, preferably less than 3% by weight of wax relative to the total weight of the composition. Advantageously, according to this embodiment, the composition is liquid at room temperature. In particular, in the case of makeup compositions, for example in the case of makeup compositions for lips, the composition can be lip gloss.

  In a second embodiment, the composition comprises at least one wax. According to this embodiment, the amount of wax in the makeup and / or care composition according to the invention is between 0.5% and 30% by weight, in particular between 1% and 20%, relative to the total weight of the composition. % By weight, or even between 2% and 15% by weight.

  In particular, the presence of a wax is preferred when the composition according to the invention is solid at room temperature. In particular, in the case of makeup compositions, for example the makeup composition for lips, the composition can be a lipstick.

The term “wax” means a lipophilic compound that is solid at room temperature (25 ° C.), with a reversible change of state of solid / liquid, has a melting point of 30 ° C. or higher, and is possible up to 200 ° C. . The wax may be selected from waxes of animal origin, plant origin, mineral origin or synthetic origin and mixtures thereof. Particular mention may be made of hydrocarbon waxes such as beeswax, lanolin wax and cinna wax; rice bran wax, carnauba wax, candelilla wax, auriculie wax, alfalfa wax, berry wax, shellac wax, wax wax and urushi wax; Montan wax, orange wax, lemon wax, microcrystalline wax, paraffin and ozokerite; polyethylene wax, waxes obtained by Fischer-Tropsch synthesis and waxy copolymers, and esters thereof. Can be further mentioned are waxes obtained by catalytic hydrogenation of animal or vegetable oils having linear or branched C ₈ -C ₃₂ fatty chains. Among these, hydrogenated sunflower oil, hydrogenated castor oil, hydrogenated coconut oil, hydrogenated lanolin oil and bis (1,1,1-trimethylolpropane) tetrastearate can be mentioned in particular. . Further mention may be made of silicone waxes and fluoro waxes. Waxes obtained by hydrogenation of castor oil esterified with cetyl alcohol can also be used.

  Advantageously, the composition according to the invention may comprise at least one wax, in particular a hydrocarbon wax.

Pasty fatty substance According to the first embodiment, the composition does not contain a pasty fatty substance.

  According to a preferred second embodiment, the composition comprises at least one pasty fatty substance. According to this embodiment, preferably the amount of pasty fatty substance in the makeup and / or care composition according to the invention is between 0.5% and 60% by weight relative to the total weight of the composition. Especially between 1% and 50% by weight, or even between 2% and 40% by weight.

  The term “pasty”, for the purposes of the present invention, exhibits an anisotropic crystal configuration in the solid state and is accompanied by a reversible change of state of the solid / liquid comprising a liquid fraction and a solid fraction at a temperature of 23 ° C. Is understood to mean a lipophilic fatty compound.

  The term “pasty compound” is understood within the meaning of the invention to mean a compound whose hardness at 20 ° C. ranges from 0.001 to 0.5 MPa, preferably from 0.002 to 0.4 MPa.

  Hardness is measured by penetrating the probe into a sample of the compound, in particular using a texture analyzer (eg Rheo TA-XT2i) equipped with a 2 mm diameter stainless steel cylinder. The hardness measurement is performed at 20 ° C. in the middle of 5 samples. A cylinder is introduced into each sample at a preliminary speed of 1 mm / s and then at a measuring speed of 0.1 mm / s with a penetration depth of 0.3 mm. The value recorded as hardness is the maximum peak hardness.

  In addition, the pasty compound is in the form of a liquid fraction and a solid fraction at a temperature of 23 ° C. In other words, the starting melting point temperature of the pasty compound is less than 23 ° C. The liquid fraction of the pasty compound measured at 23 ° C. accounts for 9 to 97% by mass of the compound. This liquid fraction at 23 ° C. preferably accounts for between 15% and 85% by weight, more preferably between 40% and 85% by weight.

  The liquid fraction of pasty compound by mass at 23 ° C. is equal to the ratio of the melting enthalpy consumed at 23 ° C. to the melting enthalpy of the pasty compound.

  The melting enthalpy of a pasty compound is the enthalpy consumed by the compound to change from the solid state to the liquid state. A pasty compound is “in the solid state” when all of its mass is in crystalline solid form. A pasty compound is “in a liquid state” when all of its mass is in liquid form.

  The enthalpy of melting of the pasty compound is, for example, 5 ° C per minute according to ISO standard 11357-3, 1999, using a differential scanning calorimeter (DSC) such as a calorimeter sold under the name MDSC 2920 by TA Instruments. Or equal to the area under the curve of the thermogram obtained with a temperature increase of 10 ° C. The melting enthalpy of a pasty compound is the amount of energy required to change the compound from a solid state to a liquid state. This is expressed in J / g.

  The melting enthalpy consumed at 23 ° C. is the amount of energy that is absorbed by the sample to change from a solid state to a state consisting of a liquid fraction and a solid fraction (this is indicated at 23 ° C.).

  The liquid fraction of the pasty compound measured at 32 ° C. is preferably 30% to 100% by weight, preferably 80% to 100% by weight, more preferably 90% to 100% by weight, based on the compound. Occupies%. When the liquid fraction of the pasty compound measured at 32 ° C. is equal to 100%, the temperature at the end of the melting range of the pasty compound is 32 ° C. or less.

  The liquid fraction of pasty compound measured at 32 ° C is equal to the ratio of the melting enthalpy consumed at 32 ° C to the melting enthalpy of the pasty compound. The melting enthalpy consumed at 32 ° C is calculated in the same way as the melting enthalpy consumed at 23 ° C.

  The pasty compound is preferably selected from synthetic compounds and compounds of plant origin. Pasty compounds can be obtained by synthesis from starting materials of plant origin. Particular mention may be made of the following, alone or as a mixture:

The pasty fatty substance is advantageously selected from:
Lanolin and its derivatives, such as lanolin alcohol, oxyethylenated lanolin, acetylated lanolin, lanolin esters, such as isopropyl lanolinate, and oxypropylenated lanolin;
-Petrolatum, specifically the product whose INCI name is Petrolatum and sold under the name Ultima White PET USP by Penreco,
-Polyol ether selected from: polyalkylene glycol pentaerythrityl ether, fatty alcohol ether of sugar, and mixtures thereof, polyethylene glycol pentaerythrityl ether containing 5 oxyethylene (5OE) units (CTFA name: PEG- 5 pentaerythrityl ether), polypropylene glycol pentaerythrityl ether containing 5 oxypropylene (5OP) units (CTFA name: PEG-5 pentaerythrityl ether), and mixtures thereof, more particularly PEG-5 pentaerythritol A mixture of lithyl ether, PPG-5 pentaerythrityl ether and soybean oil, sold under the name Lanolide by the company Vevy, which has a mass composition of 46/46/8 (46% PEG-5 Pentaerythrityl ether, 46% PPG-5 pentaerythrityl ether, and 8% soybean oil),
-Polymeric or non-polymeric silicone compounds,
-Polymeric or non-polymeric fluoro compounds,
-Vinyl polymers, especially:
Olefin homopolymers and copolymers,
Hydrogenated diene homopolymers and copolymers,
· C ₈ -C ₃₀ alkyl groups preferably have, (meth) alkyl acrylate, linear or branched oligomers, homopolymers or copolymers,
Vinyl ester oligomers, homopolymers and copolymers having C _{8 to} C ₃₀ alkyl groups,
Vinyl ether oligomers, homopolymers and copolymers having C _{8 to} C ₃₀ alkyl groups,
- one or more C ₂ -C _100, preferably liposoluble polyethers resulting from poly etherification between C ₂ -C ₅₀ diols,
-Esters (i.e. pasty fatty substances containing at least one ester function),
-And / or mixtures thereof.

Particularly preferred among the fat-soluble polyethers are copolymers of ethylene oxide and / or propylene oxide and C ₆ -C ₃₀ long chain alkylene oxides, more preferably the alkylene of ethylene oxide and / or propylene oxide in the copolymer. The mass ratio to oxide is 5:95 to 70:30. Of particular mention in this family are copolymers in which long-chain alkylene oxides are arranged in blocks with an average molecular weight of 1000 to 10,000, for example sold under the trade name Elfacos ST9 by the company Akzo Nobel. Polyoxyethylene / polydodecyl glycol block copolymers such as ethers of dodecanediol (22 mol) and polyethylene glycol (45OE).

Preferably, the pasty fatty substance comprises at least one ester functional group. Among the fatty substances of esters, the following are particularly preferred:
-Esters of glycerol oligomers, especially diglycerol esters, specifically condensates of adipic acid and glycerol, where some of the hydroxyl groups of glycerol are stearic acid, capric acid and isostearic acid, and 12-hydroxystearic acid, etc. Bis-diglyceryl polyacyl-2 adipate sold, for example, under the trade name Softisan 649 by the company Sasol,
- vinyl esters homopolymers having a C ₈ -C ₃₀ alkyl group, for example, polyvinyl laurate (sold in particular under the reference Mexomer PP by the company Chimex), and propionic acid sold under the trade name Waxenol801 by Alzo Inc. Arachidyl,
-Phytosterol esters,
Fatty acid triglycerides and derivatives thereof, such as triglycerides of fatty acids, which are in particular C ₁₀ -C ₁₈ and are partly or wholly hydrogenated, for example sold by the company Sasol under the name Softisan 100,
-Pentaerythritol ester,
A non-crosslinked polyester obtained from polycondensation of linear or branched C _{4 to} C ₅₀ dicarboxylic acids or polycarboxylic acids with C _{2 to} C ₅₀ diols or polyols,
An aliphatic ester of an ester obtained by esterification of an aliphatic hydroxycarboxylic acid ester with an aliphatic carboxylic acid. Preferably, the aliphatic carboxylic acid has 4 to 30, preferably 8 to 30 carbon atoms. It is preferably hexanoic acid, heptanoic acid, octanoic acid, 2-ethylhexanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, hexyldecanoic acid, heptadecanoic acid, It is selected from octadecanoic acid, isostearic acid, nonadecanoic acid, eicosanoic acid, isoarachidic acid, octyldodecanoic acid, heneicosanoic acid and docosanoic acid, and mixtures thereof. The aliphatic carboxylic acid is preferably branched. Aliphatic hydroxycarboxylic acid esters advantageously have 2 to 40 carbon atoms, preferably 10 to 34 carbon atoms, better 12 to 28 carbon atoms, and 1 to 20 hydroxyl groups. Derived from hydroxylated aliphatic carboxylic acids, preferably having 1 to 10 hydroxyl groups, and better still 1 to 6 hydroxyl groups. The aliphatic hydroxycarboxylic acid ester is selected from:
a) a partial or total ester of a saturated linear monohydroxylated aliphatic monocarboxylic acid,
b) a partial or total ester of an unsaturated monohydroxylated aliphatic monocarboxylic acid,
c) a partial or total ester of a saturated monohydroxylated aliphatic polycarboxylic acid,
d) a partial or total ester of a saturated polyhydroxylated aliphatic polycarboxylic acid,
e) partial esters or total esters of C ₂ -C ₁₆ aliphatic polyol have reacted with monohydroxylated or polyhydroxylated aliphatic monocarboxylic or polycarboxylic acid,
As well as mixtures thereof,
-Esters of diol dimers and diacid dimers, especially dimer dilinoleates, optionally free alcohol functions or acid functions esterified with acid groups or alcohol groups: May be selected in particular from esters having the names: bis-behenyl / isostearyl / dimermarinol dimerlinoleyl phytosteryl (commercially available under the reference names Plandool G and Plandol G7), phytosteryl / isostearyl / stearyl / Dimer linoleate behenyl (Plandol H or Plandol S) and mixtures thereof,
-Mango fats, for example, products sold under the reference name Lipex 203 by the company Aarhuskarlshamn,
-Hydrogenated oils of plant origin, such as hydrogenated isostearic acid castor oil [sold as SALACOS HCIS (VL) by Nissin Oilio Group Co., Ltd.], hydrogenated soybean oil, hydrogenated palm oil, hydrogenated rapeseed oil, Mixtures of hydrogenated vegetable oils, for example hydrogenated mixtures of soybean oil, palm oil, palm oil and rapeseed oil, such as the mixture sold under the name Akogel® by the company Aarhuskarlshamn (INCI name: Hydrogen compound vegetable oil),
-Shea butter, in particular products whose INCI name is Butyrospermum Parkii Butter, for example products sold under the reference name Sheasoft® by the company Aarhuskarlshamn,
-Hydrogenated rosin acid ester, for example dilinoleyl dimer of hydrogenated rosin acid (Lusplan DD-DHR or DD-DHR from Japan Fine Chemical Co., Ltd.),
-As well as mixtures thereof.

  Preferably, the pasty fatty substance is a hydrocarbon-based compound containing at least one SK functional group.

  Preferably, the pasty fatty substance is hydrogenated isostearic acid castor oil [SALACOS HCIS (VL) by Nissin Oilio Group Ltd.], bis-behenyl / isostearyl / dimerlinoleic acid dimerlinoleyl phytosteryl, bis -Diglyceryl polyacyl adipate-2, hydrogenated castor oil dimer linoleate [Risocast-DA-L (registered trademark), Risocast DA-H (registered trademark) sold by Higher Alcohol Industry Co., Ltd.], Selected from polyvinyl laurate, mango fat, shea fat, hydrogenated soybean oil, hydrogenated coconut oil and hydrogenated rapeseed oil, and mixtures thereof.

Filler The makeup and / or care composition according to the invention may also comprise one or more fillers.

  According to the first embodiment, the composition does not contain a filler.

  According to a preferred second embodiment, the composition comprises at least one or more fillers.

  The term “filler” should be understood to mean any form of particles, colorless or white, inorganic or synthetic, which is insoluble in the medium of the composition, regardless of the temperature at which the composition is produced. . These fillers are particularly useful for modifying the rheology or texture of the composition.

  The filler may be inorganic or organic and of any shape, small, spherical or elliptical, regardless of crystallographic form (e.g. layered, cubic, hexagonal, orthorhombic etc.) be able to. Mention may be made of talc, mica, silica, kaolin, clay, benton, fumed silica particles and polyamide [Nylon®] powder [Atochem, optionally treated with hydrophilic or hydrophobic properties. Orgasol® from], poly-β-alanine powder and polyethylene powder, tetrafluoroethylene polymer [Teflon®] powder, lauroyl lysine, starch, boron nitride, hollow polymer microspheres such as polyvinylidene chloride / Acrylonitrile microspheres such as Expancel® (Nobel Industrie), acrylic acid copolymer microspheres [eg Polytrap® from Dow Corning] and silicone resin microbeads [eg Tospearls® from Toshiba Corporation )], Precipitated calcium carbonate, magnesium carbonate, magnesium bicarbonate, hydroxyapatite, hollow silica micro [Silica Beads (R) from Maprecos], elastomeric polyorganosiloxane particles, glass or ceramic microcapsules, and organic carboxylic acids having 8 to 22 carbon atoms, and preferably 12 to 18 carbon atoms Metal soaps derived from acids, such as zinc stearate, magnesium stearate, lithium stearate, zinc laurate or magnesium myristate, and mixtures thereof.

  These may also be particles comprising a copolymer, said copolymer comprising trimethylol hexyl lactone. Specifically, they may be hexamethylene diisocyanate / trimethylol hexyl lactone copolymers. Specifically, such particles are commercially available, for example, from Toyo Pigment Co., Ltd. under the names Plastic Powder D-400 (registered trademark) or Plastic Powder D-800 (registered trademark).

  According to one preferred embodiment, the composition according to the invention comprises at least silica, preferably hydrophobically treated silica.

  According to one preferred embodiment, the composition comprises at least one filler, in particular from fumed silica, optionally treated hydrophilic or hydrophobic, preferably treated hydrophobic. Selected. Preferably, the composition comprises at least one filler known as silylated silica dimethyl (according to CTFA).

  Hydrophobic groups may in particular be dimethylsilyloxyl groups or polydimethylsiloxane groups, which are specifically treated with fumed silica in the presence of polydimethylsiloxane or dimethyldichlorosilane. Obtained by. Silicas thus treated are known as silylated silica dimethyl according to CTFA (6th edition, 1995). These include, for example, the reference names Aerosil R972® and Aerosil R974® from Degussa and Cab-O-Sil TS-610® and Cab-O-Sil TS-720 (from Cabot). Registered trademark).

  According to one particular embodiment, the composition according to the invention does not comprise “nanosilica” and preferably does not comprise hydrophobically treated silica, whose INCL name is silylated silicadimethyl. The term “nanosilica” means a silica having a nanometer size or having a fraction of at least a nanometer size.

  Preferably, the composition comprises a filler between 0.01% and 25% by weight, specifically between 0.1% and 20% by weight relative to the total weight of the composition.

  Preferably, when the composition is in liquid form, it comprises silica, kaolin, benton, fumed silica particles, preferably hydrophobically treated, and at least one filler preferably selected from lauroyllysine and starch. Including.

Preferably, the composition according to the invention can comprise a filler selected from:
-An organically modified clay, preferably treated with a compound specifically selected from quaternary amines and tertiary amines. Organic modified clays that can be mentioned are organically modified bentonites, such as products sold under the name Bentone 34 by Rheox, and organic modified hectorites, such as sold under the names Bentone 27 and Bentone 38 by Rheox. Products
-Hydrophobic fumed silica. Such silicas are, for example, the reference Aerosil R812® by Degussa and the Cab-O-Sil TS-530® by Cabot and by the reference Aerosil R972® by Degussa. Sold by Aerosil R974 (R) and Cab-O-Sil TS-610 (R) and Cab-O-Sil TS-720 (R) by Cabot.

  The filler can be present in a content ranging from 0.1% to 5% by weight and better still from 0.4% to 3% by weight relative to the total weight of the composition.

Hydrophobic Silica Airgel Particles According to a preferred embodiment, the composition may comprise at least hydrophobic silica airgel particles. Such a compound is a filler.

  Preferably, such compounds are present when the composition does not contain nanosilica, and more particularly when it does not contain silylated silica dimethyl.

  Preferably, the hydrophobic silica airgel particles can be present in a content ranging from 0.1% to 15% by weight and better still from 0.1% to 10% by weight relative to the total weight of the composition.

  Preferably, the hydrophobic silica airgel particles can be present in a content ranging from 0.1% to 6% by weight and better still from 0.2% to 4% by weight relative to the total weight of the composition.

  According to this embodiment, the composition may comprise at least an additional filler, for example as previously described as an example.

  Preferably, the composition according to the invention comprises at least hydrophobic silica airgel particles when the composition does not comprise the previously described nanometer silica particles, such as silica dimethyl silylate.

  Silica airgel is a porous material obtained by replacing (by drying) the liquid component of silica gel with air.

These are generally sol - in a liquid medium through a gel process, then typically is dried by extraction with supercritical fluids, which are most commonly used is supercritical CO _2. This type of drying can avoid pore shrinkage and shrinkage of the material. The sol-gel method and various drying methods are described in detail in Brinker CJ and Scherer GW, Sol-Gel Science, New York, Academic Press, 1990.

Hydrophobic silica airgel particles which may be used in the present invention, the specific surface (S _M) is 500 to 1500 ² / g per mass unit, preferably 600~1200m ² / g, better still 600~800m ² / g The size represented by the volume average diameter (D [0.5]) is 1 to 1500 μm, better 1 to 1000 μm, preferably 1 to 100 μm, specifically 1 to 30 μm, more preferably 5 to 25 μm, The range is more preferably 5 to 20 μm, and still more preferably 5 to 15 μm.

  According to one embodiment, the hydrophobic silica airgel particles that can be used in the present invention have a size represented by a volume average diameter (D [0.5]) of 1 to 30 μm, preferably 5 to 25 μm, and more preferably 5 to 5 μm. The range is 20 μm, and even better, 5-15 μm.

  The specific surface area per mass unit can be determined via the BET (Brunauer-Emmett-Teller) nitrogen absorption method, which is described in The Journal of the American Chemical Society, Vol. 60, p. 309, 1938. It is described in February, and corresponds to the international standard ISO 5794/1 (Appendix D). The BET specific surface area corresponds to the total specific surface area of the particles under consideration.

  The size of the hydrophobic silica airgel particles can be measured by static light scattering using a commercially available particle size analyzer such as the MasterSizer 2000 machine from Malvern. Data is processed based on Mie scattering theory. This theory is rigorous for isotropic particles and makes it possible to determine an “effective” particle size in the case of non-spherical particles. This theory is specifically described in the publication “Light Scattering by Small Particles” chapters 9 and 10 by Van de Hulst, H.C., Wiley, New York, 1957.

According to one advantageous embodiment, the hydrophobic silica airgel particles used in the invention have a specific surface area per unit of mass (S _M ) in the range of 600 to 800 m ² / g and a volume average diameter (D [ The size represented by 0.5]) ranges from 5 to 20 μm, and more preferably from 5 to 15 μm.

Hydrophobic silica airgel particles used in the present invention are advantageously packing density ρ is 0.04 g / cm ³ from 0.10 g / cm ^3, preferably in the range of 0.08 g / cm ³ from 0.05 g / cm ³ be able to.

  In the context of the present invention, this density is known as the packing density and can be assessed according to the following protocol:

Pour 40 g of powder into a graduated cylinder; then place the graduated cylinder on a Stampf Volumeter Stav2003 machine; then subject the graduated cylinder to a series of 2500 filling motions (this operation is the volume between two consecutive tests) Until the difference is less than 2%); then the final volume Vf of the filled powder is measured directly with a graduated cylinder. The packing density is determined by the ratio m / Vf (Vf is expressed in cm ³ and m is expressed in g), in this case 40 / Vf.

According to one embodiment, the hydrophobic silica airgel particles which may be used in the present invention, 1 volume specific surface area per unit S _v is 5~60m ² / cm ^3, preferably 10 to 50 m ² / cm ^3, better Ranges from 15 to 40 m ² / cm ³ .

The specific surface area per volume unit is obtained by the following relation:
S _v = S _M xρ (as defined above, where ρ is the packing density expressed in g / cm ³ and S _M is the ratio per volume unit expressed in m ² / g. Surface area).

  Preferably, the hydrophobic silica airgel particles according to the present invention have an oil absorption capacity ranging from 5 to 18 ml / g, preferably from 6 to 15 ml / g, better still from 8 to 12 ml / g, measured at the wet point. To do.

  The oil absorption capacity, measured at the wet point, is written as Wp and corresponds to the amount of oil that needs to be added to 100 g of particles in order to obtain a homogeneous paste.

  This is measured according to the “wet point” method or the method for determining the oil uptake of powder as described in the NF T30-022 standard. This corresponds to the amount of oil adsorbed on the vacant surface of the powder by measuring the wet point and / or the amount of oil absorbed into the powder by determining the wet point and is described below:

  An amount m = 2 g of powder is placed on a glass plate and then oil (isonononyl isononanoate) is added dropwise. Add 4 to 5 drops of oil to the powder, then mix with a spatula and add the oil until an assembly of oil and powder is formed. At this moment, one drop of oil is added at a time and then the mixture is ground with a spatula. When a firm and smooth paste is obtained, stop adding oil. This paste must be able to spread on the glass plate without cracking or forming lumps. Then write down the volume of oil used, Vs (expressed in ml).

  The amount of oil taken up corresponds to the ratio Vs / m.

  The hydrophobic silica airgel particles that can be used according to the invention are preferably of the silylated silica type (INCI name: silylated silica).

  The term “hydrophobic silica” refers to the halogenation of any silica whose surface has been treated with a silylating agent, eg alkylchlorosilane, in order to functionalize the OH groups with silyl Si—Rn groups, eg trimethylsilyl groups. Silane, siloxane, especially dimethylsiloxane such as hexamethyldisiloxane, or silazane.

  For the preparation of hydrophobic silica airgel particles that are surface modified by silylation, reference may be made to US Pat. No. 7,707,725.

  Of particular use are hydrophobic silica airgel particles surface modified with trimethylsilyl groups.

Examples of hydrophobic silica airgel particles that can be used in the present invention include an airgel sold under the name VM-2260 (INCI name: silylated silica) by the company Dow Corning, the particles having an average size. Is about 1000 microns, and the specific surface area per mass unit is in the range of 600 to 800 m ² / g.

  Further mention may be made of the aerogels sold by Cabot under the reference names Aerogel TLD201, Aerogel OGD201, Aerogel TLD203 and ENOVA AEROGEL MT1100.

More specifically used is an airgel sold under the name VM-2270 (INCI name: silylated silica) by Dow Corning, whose particles range in average size from 5 to 15 microns. The specific surface area per mass unit ranges from 600 to 800 m ² / g (oil intake equal to 1080 ml / 100 g).

Advantageously, the hollow particles according to the invention are at least partly formed from hydrophobic silica airgel particles, preferably having a specific surface area per unit of mass (S _M ) in the range of 500-1500 m ² / g, Preferably, the size is 600 to 1200 m ² / g, and the size expressed by volume average diameter (D [0.5]) is 1 to 1500 μm, more preferably 1 to 1000 μm, preferably 1 to 100 μm, specifically 1 to 30 μm. More preferably, the range is 5 to 25 μm, more preferably 5 to 20 μm, and still more preferably 5 to 15 μm.

  The use of hydrophobic silica airgel particles can also advantageously improve the stability of the composition.

Dextrin esters Preferably, the composition according to the invention are esters of at least dextrin, preferably an ester of dextrin with a fatty acid may preferably comprise a C ₁₂ -C ₂₄ fatty acids.

Preferably, the dextrin ester is an ester of dextrin and a C ₁₄ -C ₁₈ fatty acid.

  Preferably, the dextrin ester is dextrin palmitate, such as that marketed by Chiba Flour Mills under the reference name Rheopearl TL® or Rheopearl KL®.

  Preferably, the composition according to the invention can comprise a dextrin ester in a content ranging from 0.1% to 15% by weight, preferably from 0.5% to 10% by weight, relative to the total weight of the composition. .

  Preferably, the composition according to the invention can comprise dextrin esters in a content ranging from 1% to 8% by weight, preferably from 2% to 6% by weight, based on the total weight of the composition. .

  According to one particular embodiment, the composition according to the invention does not contain dextrin esters.

Dye The composition according to the present invention may preferably comprise at least one dye (also known as a colorant), which is a water-soluble or fat-soluble dye, pigment and pearlescent agent, and A mixture thereof may be selected.

  The composition according to the invention can also comprise one or more dyes selected from water-soluble dyes and powdered dyes, such as pigments, pearlescent agents and glitter flakes, which are well known to those skilled in the art. is there.

  The dye can be present in the composition in a content of 0.01% to 30% by weight, preferably 0.1% to 20% by weight, based on the weight of the composition.

  The term “pigment” should be understood as meaning white or colored, inorganic or organic particles that are insoluble in aqueous solutions intended to color and / or opacify the resulting coating. .

  The pigment can be present in a proportion of 0.01% to 30% by weight, in particular 0.1% to 25% by weight, in particular 0.2% to 15% by weight, based on the total weight of the cosmetic composition.

  Mentioned as inorganic pigments that can be used in the present invention are titanium oxide, zirconium oxide or cerium oxide, and also zinc oxide, iron oxide or chromium oxide, ferric blue, manganese violet, ultramarine blue and chromium hydroxide. .

  It can also be a pigment having a structure which may be of the type sericite / brown iron oxide / titanium dioxide / silica, for example. Such pigments are sold, for example, by Chemicals and Catalysts under the reference Coverleaf NS or JS and have a contrast ratio in the region of 30.

  The dye can also include a pigment having a structure that may be, for example, a type of silica microspheres containing iron oxide. An example of a pigment having this structure is a product sold by Miyoshi Kasei Co., Ltd. under the reference name PC BALL PC-LL-100P, which consists of silica microspheres containing yellow iron oxide.

  Among the organic pigments that can be used in the present invention, mention may be made of carbon black, D & C type pigments, cochineal carmine-based or barium-based, strontium-based, calcium-based or aluminum-based lakes, or alternatively European patents. There are diketopyrrolopyrrole (DPP) described in A-542669, European Patent A-787730, European Patent A-787731 and International Publication A-96 / 08537.

  The term “pearlescent agent” may or may not be iridescent, specifically produced in its shell by certain molluscs, or otherwise synthesized, and optical interferences. It should be understood to mean any form of colored particles having a color effect therethrough.

  Pearlescent agents are based on titanium mica coated with iron oxide, mica coated with bismuth oxychloride, titanium mica coated with chromium oxide, titanium mica coated with organic dyes, and also bismuth oxychloride It can be selected from pearlescent pigments such as pearlescent pigments. They can also be mica particles on the surface of which at least two continuous phases of metal oxide and / or organic dye are laminated.

  Further examples of pearlescent agents that may be mentioned are natural mica coated with titanium oxide, with iron oxide, with natural pigments or with bismuth oxychloride.

  Among the commercially available pearlescent agents are the pearlescent agents Timica, Flamenco and Duochrome sold by Engelhard, the Timiron pearlescent agent sold by Merck, Eckart Prestige mica-based pearlescent agent sold by the company and Sunshine synthetic mica-based pearlescent agent sold by Sun Chemical.

  The pearlescent agent can have a color or shade of yellow, peach, red, bronze, orange, brown, gold and / or copper, more particularly.

  Examples of pearlescent agents that can be used in the context of the present invention are the names Brilliant gold212G (Timica), Gold222C (Cloisonne), Sparkle gold (Timica), Gold4504 (Chromalite) and Monarch gold233X, in particular by Engelhard. Golden pearlescent agent sold under (Cloisonne); in particular sold under the name Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona) by Merck and under the name Super bronze (Cloisonne) by Engelhard Bronze pearlescent agents; in particular sold by Engelhard under the names Orange363C (Cloisonne) and Orange MCR101 (Cosmica) and by Merck under the names Passion orange (Colorona) and Matte orange (17449) (Microna) Orange pearlescent agents; especially brown pearlescent agents sold under the names Nu-antique copper340XB (Cloisonne) and Brown CL4509 (Chromalite) by Engelhard; in particular sold under the name Copper340A (Timica) by Engelhard Has a copper tint A pearlescent agent with a red tint sold by Merck under the name Sienna fine (17386) (Colorona); in particular yellow sold under the name Yellow (4502) (Chromalite) by Engelhard A pearlescent agent with a gold shade, especially sold under the name Sunstone G012 (Gemtone) by Engelhard; in particular sold under the name Tan opale G005 (Gemtone) by Engelhard Pink pearlescent agent; in particular black pearlescent agent with gold shade sold under the name Nu antique bronze240AB (Timica) by Engelhard; in particular sold under the name Matte blue (17433) (Microna) by Merck Blue pearlescent agents; especially white pearlescent agents with a silvery hue sold under the name Xirona Silver by Merck; and especially gold-colored sold under the name Indian summer (Xirona) by Merck Green, pinkish o Nji color pearlescent agent, as well as mixtures thereof.

  The term “dye” should be understood to mean compounds that are generally organic compounds and are soluble in fatty substances such as oils or in the hydroalcoholic phase.

  The cosmetic composition according to the invention can also comprise water-soluble or fat-soluble dyes. The fat-soluble dyes are, for example, Sudan Red, DC Red 17, DC Green 6, β-carotene, Sudan Brown, DC Yellow 11, DC Violet 2, DC Orange 5, and quinoline yellow. The water-soluble dye is, for example, beetroot juice or methylene blue.

  The cosmetic composition according to the invention can also contain at least one material with special optical effects as a dye.

  This effect is different from simple prior art tone effects, i.e. unified and stabilized effects such as standard dyes, such as monochromatic pigments. For the purposes of the present invention, the term “stabilized” means that there is no effect of color variation in response to temperature changes or alternatively in response to viewing angles.

  For example, this material can be selected from metallic shades, goniochromatic coloring agents, diffractive pigments, thermochromic agents, optical brighteners, and particles with fibers, in particular interference fibers. Needless to say, these various substances can be combined to provide two effects simultaneously, or even the manifestation of a novel effect according to the present invention.

Aqueous Phase The composition of the invention may also comprise an aqueous phase, which is 1% to 80% by weight, in particular 2% to 70% by weight, or even 3%, based on the total weight of the composition. The mass can be comprised between 60% and 60% by mass. This aqueous phase can be formed essentially from water, or water and a water-miscible solvent (miscible with more than 50% by weight in water at 25 ° C.) (especially 1-5 carbon atoms). monoalcohols having, for example, ethanol or isopropanol, glycols having from 2 to 8 carbon atoms, such as propylene glycol, ethylene glycol, 1,3-butylene glycol, dipropylene glycol, C ₃ -C ₄ ketones, C ₂ -C ₄ aldehydes, and can comprise a mixture of selected) mixtures thereof.

  However, as specified above, advantageously, the composition according to the invention is anhydrous.

  The term “anhydride” specifically means that water is preferably not intentionally added to the composition, but may be present in trace amounts in the various compounds used in the composition.

Additives The makeup and / or care compositions according to the invention may also comprise at least one agent commonly used in cosmetics, for example reducing agents, thickeners, which are particularly hydrophobic. , Film forming agents, silicone elastomers, softeners, antifoams, wetting agents, UV screening agents, ceramides; cosmetic active agents; peptizers, fragrances, proteins, vitamins, sprays, hydrophilic or lipophilic, synthetic Film- or non-film-forming polymer; selected from lipophilic or hydrophilic gelling agents. The above-mentioned additives are generally present in their respective amounts between 0.01% and 10% by weight relative to the total weight of the composition. Of course, those skilled in the art will carefully select the composition of the composition such that the advantageous properties associated with the present invention are not or substantially not adversely affected.

Conventional Additional Cosmetic Ingredients The composition used according to the present invention may also contain any conventional cosmetic ingredients, which are in particular antioxidants, film-forming polymers, perfumes, preservatives, softeners, Wetting agents, neutralizing agents, sunscreens, sweeteners, vitamins, free radical scavengers and sequestering agents, and mixtures thereof may be selected.

  The amount of each of these various components is the amount conventionally used in the envisaged field, for example, ranging from 0.01% to 10% by weight relative to the total weight of the composition.

  Of course, those skilled in the art will recognize optional additional ingredients and / or such that the advantageous properties of the composition according to the present invention are not or substantially not adversely affected by the envisaged addition. You will choose these quantities carefully.

  The composition according to the invention can be in liquid or solid form.

  According to a first embodiment, the composition is in solid form. In particular, it can be a cosmetic product selected from lip balms and / or lipsticks. The product is preferably in the form of a stick or in the form of a cast in the dish.

  According to one embodiment, it is a lipstick or a lip balm in stick form.

  The composition according to the invention may constitute a liquid lipstick for lips, a body makeup product, a facial or body care product, or a sunscreen product.

  According to one preferred embodiment, the composition of the invention is in liquid form. An example of a liquid formulation that can be mentioned in particular is lip gloss.

  As mentioned earlier, the composition according to the invention is homogeneous and stable, in particular in terms of gloss, comfort (sediment depth) and absence of sediment color transfer. Make available deposits on skin or lips with cosmetic properties. In particular, the composition according to the invention specifically forms a deposit in which the lip product does not transfer on the cup while drinking when the composition contains one or more colorants. Can do.

  In the description, and in the examples that follow, unless stated otherwise, percentages are percent by weight and ranges of values given in the form of “between ...” are described. Including lower and upper limits.

  Unless otherwise stated, the values in the following examples are expressed in% by weight relative to the total weight of the composition.

  The following examples are presented as non-limiting illustrations in the technical field of the present invention.

Synthesis of supramolecular polymer 100 g of dihydroxylated hydrogenated 1,2-polybutadiene polymer (GI3000 from Nippon Soda Co., Ltd., measured as Gn = 4700 by GPC according to the protocol described above) at 80 ° C. under reduced pressure. Dry overnight. This polymer is dissolved in 400 ml of anhydrous toluene. 25 μl of catalyst (dibutyltin dilaurate) is added and the mixture is heated to 80 ° C. with stirring until a homogeneous solution is obtained. 15 g of isocyanate-functionalized molecules of the following structure:

Is added as a solution in 300 ml of anhydrous toluene at 40 ° C. under a controlled atmosphere. The reaction mixture is heated to 100 ° C. and stirred at this temperature for 4 hours. The reaction is monitored by infrared spectroscopy until complete disappearance at the isocyanate characteristic peak of 2260 cm ⁻¹ . At the end of the reaction, 100 ml of ethanol is added to remove all traces of residual isocyanate, then isododecane is added to reduce the viscosity of the solution and then the mixture is filtered. The polymer solution is then stripped directly with isododecane.

  A solution of the final polymer in isododecane with a solid content of 21% was obtained and the polymer was analyzed by GPC (Mn = 6400, polydispersity index = 1.85) and by 1H NMR (in agreement with what was expected) Spectrum) and characterize.

Synthesis of supramolecular polymer Synthesis of ureidopyrimidone bifunctional polymer GI2000

106.1 g of dihydroxylated hydrogenated 1,2-polybutadiene polymer (GI 2000 from Nippon Soda Co., Ltd., determined by GPC to have Mn = 3300 according to the protocol described above) in the presence of 22 mg of catalyst (dibutyltin dilaurate), Heat at 80 ° C. under reduced pressure for 2 hours. The temperature of the mixture is reduced to 20 ° C. under argon, after which 10 ml of isododecane and 19.3 g of isophorone diisocyanate (IPDI) are added. The mixture is stirred at 20 ° C. under a controlled atmosphere for 16 hours, then it is heated to 120 ° C., after which 25 ml of propylene carbonate is added. Addition of 12 g of 6-methylisocytosine results in a uniform white suspension. The suspension is heated to 140 ° C. and stirred at this temperature for 6 hours. The reaction is monitored by infrared spectroscopy until the complete disappearance of the isocyanate characteristic peak (2250 cm ⁻¹ ). The mixture is then lowered to 30 ° C. and 400 ml heptane, 200 ml THF and 50 ml ethanol are added followed by filtration through celite. The mixture is then stripped with isododecane.

  A solution of polymer in isododecane with a solids content of 25% is finally obtained and the polymer is characterized by GPC (Mn = 7000, polydispersity index = 2.05).

Synthesis of supramolecular polymer Dihydroxylated hydrogenated 1,2-polybutadiene polymer (GI3000 from Nippon Soda Co., Ltd., measured as Mn = 4700 by GPC according to the protocol described above) 99 g, catalyst (dibutyltin dilaurate) 22 mg For 2 hours at 80 ° C. under reduced pressure. The temperature of the mixture is lowered to 20 ° C. under argon, after which 30 ml of isododecane and 11 g of isophorone diisocyanate (IPDI) are added. The mixture is stirred at 20 ° C. under a controlled atmosphere for 16 hours, then it is heated to 120 ° C., after which 25 ml of propylene carbonate is added. Addition of 8.1 g of 6-methylisocytosine results in a homogeneous white suspension. The suspension is heated to 140 ° C. and stirred at this temperature for 6 hours. The reaction is monitored by infrared spectroscopy until the complete disappearance of the isocyanate characteristic peak (2250 cm ⁻¹ ). The mixture is then lowered to 30 ° C. and 1 liter of heptane is added followed by filtration through celite. The mixture is then stripped with isododecane.

  A solution of the polymer in solid isododecane with a solids content of 20% is finally obtained and the polymer is characterized by GPC (Mn = 4200, polydispersity index = 2.34).

Synthesis of supramolecular polymer Dihydroxylated hydrogenated 1,2-polybutadiene polymer (GI3000 from Nippon Soda Co., Ltd., measured as Gn = 4700 by GPC according to the protocol described above) 89 g, presence of catalyst (dibutyltin dilaurate) 22 mg Heat at 80 ° C. under reduced pressure for 2 hours. The temperature of the mixture is reduced to 20 ° C. under argon, after which 60 ml of isododecane and 11.6 g of 4,4′-dicyclohexylmethane diisocyanate are added. The mixture is stirred at 20 ° C. under a controlled atmosphere for 16 hours, then it is heated to 120 ° C., after which 40 ml of propylene carbonate are added. The addition of 6.64 g of 6-methylisocytosine results in a homogeneous white suspension. The suspension is heated to 140 ° C. and stirred at this temperature for 8 hours. The reaction is monitored by infrared spectroscopy until the complete disappearance of the isocyanate characteristic peak (2250 cm ⁻¹ ). The mixture is then cooled to 30 ° C., 250 ml of isododecane and 500 ml of heptane are added and then filtered through celite. The mixture is then stripped with isododecane.

  A solution of the polymer in solid isododecane with a solids content of 22% is finally obtained and the polymer is characterized by GPC (Mn = 10700, polydispersity index = 2.26).

Synthesis of supramolecular polymer Dihydroxylated hydrogenated 1,2-polybutadiene polymer (GI2000 from Nippon Soda Co., Ltd., measured as Gn = 3300 by GPC according to the protocol described above) 143.1 g, catalyst (dibutyltin dilaurate) 33 mg Heat in the presence at 80 ° C. under reduced pressure for 2 hours. The temperature of the mixture is lowered to 20 ° C. under argon, after which 85 ml of isododecane and 30.8 g of 4,4′-dicyclohexylmethane diisocyanate are added. The mixture is stirred at 20 ° C. under a controlled atmosphere for 16 hours, then it is heated to 120 ° C., after which 70 ml of propylene carbonate are added. Addition of 22.6 g of 6-methylisocytosine results in a homogeneous white suspension. The suspension is heated to 140 ° C. and stirred at this temperature for 8 hours. The reaction is monitored by infrared spectroscopy until the complete disappearance of the isocyanate characteristic peak (2250 cm ⁻¹ ). The mixture is then cooled to 20 ° C., 700 ml of isododecane and 500 ml of heptane are added and then filtered through celite. The mixture is then stripped with isododecane.

  A solution of the polymer in isododecane with a solids content of 20% is finally obtained and the polymer is characterized by GPC (Mn = 8400, polydispersity index = 2.00).

(Examples 1 to 5)
Liquid Lipstick Type (Gloss) Cosmetic Formulations Two liquid makeup gloss compositions according to the present invention (see Table 1) were prepared (see Table 1) with the following compositions (the percentages shown are% by weight): ). Formulations 1 and 2 illustrate the present invention.

Method of Preparation Compositions 1 and 2 were obtained according to the following protocol:

  In the first stage, the filler and pigment were ground in a three-roll kneader in some oil phase (in disostearyl malate).

  In parallel, the supramolecular polymer according to the invention was mixed with silicone oil and ground pigment material in a beaker or heated pan. The mixture was then stirred in a Reinelli mixer until homogeneous. The ground pigment material was then incorporated into the mixture and stirring was continued until the mixture was homogeneous.

  Finally, the composition was left at room temperature for 24 hours and then adjusted in a heated bag.

  Composition embodiment at room temperature (25 ° C.): Formulation 1 and Formulation 2 were homogeneous after 24 hours at room temperature and after 72 hours at room temperature and after 72 hours at 42 ° C. A stable composition is formed. Specifically, no phase separation occurs and no settling occurs.

Evaluation of the composition
-Viscosity The viscosities of compositions 1 and 2 at 25 ° C were measured according to the protocol described above.

-Luminance The brightness of the deposit obtained on the lips with the composition was measured using the Polka SEI-M-0216-Polk-02 polarized camera and the Chromasphere SEI-M-02232 described in French patent application No. 2829344. -Evaluated using CHRO-0. Luminance is evaluated immediately after application and at T1 = 1 hour and T2 = 2 hour after application of the formulation.

Color transfer resistance Color transfer resistance is assessed by drinking from a white cup and putting on the lips 5 minutes after the composition is applied to the lips.
-Payoff
-Stickiness The sticky nature of the deposit made on the lips with the formulation to be evaluated is evaluated by rubbing the upper and lower lips together 5 minutes after application and the stickiness is Were rated when removed from the upper and lower lips.

The measurements taken are considered as follows:
+ No stickiness during drying
++ Slight sticking effect during drying
+++ Moderate sticking effect during drying
++++ Strong adhesive effect during drying
+++++ Very strong adhesive effect during drying

  The following results were obtained:

  What emerges from these results is that the composition according to the invention is capable of producing a makeup deposit on the lips that is shiny and has little or no tackiness. Both compositions 1 and 2 are easy to apply (good slip) and are homogeneous deposits. The deposits formed with the composition according to the invention also have good color transfer resistance properties and a good level of brightness immediately after application and after 1 hour.

  Especially for composition 1, the color transfer level of the deposit is very low, and the deposit obtained with composition 2 is not sticky.

Claims (24)

In a physiologically acceptable medium,
- wherein HO-P-OH [wherein, P is one or a plurality, linear, cyclic and / or branched polyunsaturated C ₂ -C ₁₀ alkenes, preferably C ₂ -C ₄ alkene Which represents a homopolymer or copolymer obtainable by polymerization of at least one functionalized polyalkene polymer and at least one functionalized with at least one reactive group capable of reacting with a reactive group of the functionalized polyalkene polymer. It is possible to derive from reaction with one linking group, in particular from condensation, said linking group comprising at least 3 H (hydrogen) bonds, preferably at least 4 H bonds, preferentially 4 H bonds At least one supramolecular polymer based on a functionalized polyalkene of
-At least one, preferably phenylated, non-volatile silicone oil;
-A composition for making up and / or caring for the skin and / or lips, comprising at least one non-volatile hydrocarbonated oil, preferably a nonpolar hydrocarbonated oil.   2. The composition of claim 1, wherein the functionalized polyalkene of formula HO-P-OH is hydrogenated. P is one or more linear or branched di-unsaturated C ₂ -C ₄ represents a homopolymer or copolymer obtainable by polymerization of alkenes, composition according to claim 1 or 2.   P represents polybutylene, polybutadiene, polyisoprene, poly (1,3-pentadiene) or polyisobutylene, and copolymers thereof, preferably poly (ethylene / butylene). Composition. The functionalized linking group has the formula:

Wherein L is particularly selected from linear or branched C ₁ -C ₂₀ alkylene, C ₅ -C ₂₀ (alkyl) cycloalkylene, alkylene-biscycloalkylene and C ₆ -C ₂₀ (alkyl) arylene. is selected, a divalent C ₁ -C ₂₀ carbon-based radical saturated or unsaturated, preferably isophorone group)
5. The composition according to any one of claims 1 to 4, wherein The supramolecular polymer has the formula:

(Where
-L 'and L'', independently of one another, are as defined for L in claim 5;
-X, X '= O, and P is as defined in any one of claims 1 to 5)
The composition according to any one of claims 1 to 5, corresponding to: -L 'and L''are both isophorone groups,
-X and X '= O and P represents polybutylene, polybutadiene, polyisoprene, poly (1,3-pentadiene) or polyisobutylene, and copolymers thereof, preferably poly (ethylene / butylene). 6. The composition according to 6.   Any one of claims 1 to 7, comprising from 3% to 60%, preferably from 3.5% to 50%, or even from 4% to 40% by weight of supramolecular polymer relative to the total weight of the composition. A composition according to claim 1.   The non-volatile hydrocarbonated oil is a non-polar hydrocarbonated oil, preferably selected from polybutene, hydrogenated polybutene, polyisobutene, hydrogenated polyisobutene, polydecene, hydrogenated polydecene, and mixtures thereof. 9. The composition according to any one of 8.   10. The composition according to any one of claims 1 to 9, wherein the non-volatile silicone oil is a phenylated silicone oil. The non-volatile phenylated silicone oil is
a) Phenyl silicone oil corresponding to the following formula (I)

(Wherein the R groups independently of one another represent methyl or phenyl, provided that at least one R group represents phenyl, preferably at least the R group represents a phenyl group),
b) Phenyl silicone oil corresponding to the following formula (II)

(Wherein the R groups independently of one another represent methyl or phenyl, provided that at least one R group represents phenyl, preferably at least the R group represents phenyl),
c) Phenyl silicone oil corresponding to the following formula (III)

[In the formula, Me represents methyl, Ph represents phenyl, and preferably 1,3,5-trimethyl-1,1,3,5,5-pentaphenyltrisiloxane (INCI name: trimethylpentaphenyltrisiloxane) And tetramethyltetraphenyltrisiloxane],
d) Phenyl silicone oil corresponding to the following formula (IV)

[Wherein Me represents methyl, y is between 1 and 1000, and X represents —CH ₂ —CH (CH ₃ ) (Ph)],
e) Phenyl silicone oil corresponding to the following formula (V)

[Wherein Me is methyl, Ph is phenyl, OR ′ represents an —OSiMe ₃ group, y is 0, or ranges between 1 and 1000, and z is from 1 to 1000. In particular, y and z are the numbers at which compound (V) becomes a non-volatile oil, preferably when y is between 1 and 1000, for example trimethylsiloxyphenyl dimethicone. , Preferably when y is equal to 0, for example phenyltrimethylsiloxytrisiloxane],
f) Phenyl silicone oils corresponding to the following formula (VI), and mixtures thereof

(Where
R ₁ to R ₁₀ are, independently of one another, saturated or unsaturated, linear, cyclic or branched C _{1 to} C ₃₀ hydrocarbon-based groups;
-m, n, p and q are each independently an integer between 0 and 900, provided that the sum m + n + q is not 0, preferably the sum m + n + q is 1 to 100. Preferably, the sum m + n + p + q is between 1 and 900, preferably q is equal to 0, preferably R ₁ to R ₁₀ are, independently of one another, saturated or unsaturated, linear or branched C ₁ -C ₃₀ hydrocarbon group, preferably a saturated, C ₄ in particular C ₁ -C ₁₂ hydrocarbon-based radical, in particular C ₃ -C _16, more particularly To C ₁₀ , or monocyclic or polycyclic C _{6 to} C ₁₄ , especially C _{10 to} C ₁₃ aryl groups, or aralkyl groups. Preferably, R ₁ to R ₁₀ can each represent a methyl, ethyl, propyl, butyl, isopropyl, decyl, dodecyl or octadecyl group, or alternatively a phenyl, tolyl, benzyl or phenethyl group. R ₁ to R ₁₀ may in particular be identical and in addition may be a methyl group),
g) Phenyl silicone oils corresponding to the following formula (VII) and mixtures thereof

[Where
R _{1 to} R ₆ are, independently of one another, saturated or unsaturated, linear, cyclic or branched C _{1 to} C ₃₀ hydrocarbon-based groups, preferably R ₁ to R ₆ are C ₁ -C ₃₀ alkyl group, an aryl group or an aralkyl group,
-m, n and p are, independently of one another, an integer between 0 and 100, provided that the sum n + m is between 1 and 100;
Preferably, R ₁ to R ₆ are, independently of one another, saturated or unsaturated, linear or branched C _{1 to} C ₃₀ hydrocarbon groups, preferably saturated, in particular C _{1 to} C ₁₂ carbonization. It represents a hydrogen-based group, in particular C _{3 to} C ₁₆ , more particularly C _{4 to} C ₁₀ , or a monocyclic or polycyclic C _{6 to} C ₁₄ , in particular C _{10 to} C ₁₃ aryl group, or an aralkyl group. Preferably R ₁ to R ₆ may each represent a methyl, ethyl, propyl, butyl, isopropyl, decyl, dodecyl or octadecyl group, or alternatively a phenyl, tolyl, benzyl or phenethyl group, preferably R ₁ To R ₆ may be in particular identical and in addition may be a methyl group, preferably in formula (VII), m = 1 or 2 or 3 and / or n = 0, And / or p = 0 or 1 can be applied),
h) Phenyl silicone oils corresponding to the following formula (IX), and mixtures thereof

(Where
R ₁ , R ₂ , R ₅ and R ₆ are alkyl groups having 1 to 6 carbon atoms together or separately, and R ₃ and R ₄ are 1 to 6 together or separately. An alkyl group having 1 carbon atom or an aryl group, provided that at least one of R ₃ and R ₄ is a phenyl group, and X is an alkyl group having 1 to 6 carbon atoms, a hydroxyl group, or vinyl. N and p are integers greater than or equal to 1 selected to give the oil a weight average molecular weight of less than 200,000 g / mol, preferably less than 150,000 g / mol, more preferably less than 100,000 g / mol)
11. A composition according to any one of claims 1 to 10, selected from i) as well as mixtures thereof. The non-volatile phenylated silicone oil is
-Phenyltrimethicone,
-Tetramethyltetraphenyltrisiloxane
-Diphenylsiloxyphenyl trimethicone,
-Diphenylsiloxyphenyl dimethicone,
-Trimethylpentaphenyltrisiloxane,
-Phenyl dimethicone,
-Phenyltrimethylsiloxydiphenylsiloxane,
-Diphenyl dimethicone,
-Diphenylmethyldiphenyltrisiloxane, and
-2-phenylethyltrimethylsiloxysilicate,
12. A composition according to any one of claims 1 to 11, selected from: and mixtures thereof. Said non-volatile phenylated silicone oil has the formula (VII) wherein m, n, p and R ₁ to R ₆ are as defined above, preferably R ₁ to R ₆ are methyl groups. Wherein m = 0 and n and p are each independently an integer between 1 and 100), preferably the silicone oil is selected from diphenyl dimethicone 13. The composition according to claim 11 and 12, wherein Said non-volatile phenylated silicone oil is of the formula (VII) wherein m, n, p and R ₁ to R ₆ are as defined above, preferably R ₁ to R ₆ are methyl groups Wherein p is between 1 and 100, and the sum n + m is between 1 and 100 and n = 0), preferably selected from the silicone 13. Composition according to claims 11 and 12, wherein the oil is selected from trimethylsiloxyphenyl dimethicone. The non-volatile phenylated silicone oil is selected from phenyl dimethicone oils corresponding to formula (VII), preferably
-Diphenyl dimethicone,
-Trimethylsiloxyphenyl dimethicone,
15. A composition according to claims 13 and 14, selected from-and mixtures thereof.   Said non-volatile silicone oil is preferably selected from polydimethylsiloxane, alkyl dimethicone, vinyl methyl methicone, and optionally modified with fluorinated aliphatic groups, or hydroxyl groups, thiol groups and / or amine groups 10. A non-phenylated silicone oil preferably selected from silicones modified with functional groups such as polydimethylsiloxane, preferably a dimethicone oil preferably selected from alkyl dimethicones. The composition as described in any one of these.   17 to 70% by weight, preferably 0.2% to 40% by weight, or even a total of 0.3% to 30% by weight of silicone oil relative to the total weight of the composition. The composition according to any one of the above.   From further comprising at least one additional compound preferably selected from hydrocarbonated polar oils and / or fatty pasty compounds and / or fillers, and / or colorants, and / or mixtures thereof. 18. The composition according to any one of items 17.   19. A composition according to any one of the preceding claims comprising at least one filler, for example silica and / or hydrophobic silica.   Further comprising hydrophobic silica airgel particles, preferably hydrophobic silica allogel particles surface-modified with trimethylsilyl groups, preferably from 0.1% to 15% by weight, and better still from 0.1% by weight, based on the total weight of the composition 20. A composition according to any one of the preceding claims comprising a content ranging from 10% by weight, preferably from 0.1% to 6% by weight, and better still from 0.2% to 4% by weight. Dextrin with a fatty acid, preferably C ₁₂ -C esters of ₂₄ fatty acid, preferably further comprises dextrin palmitate, composition according to any one of claims 1 to 20.   The composition according to any one of claims 1 to 21, which is a lip product such as a lipstick, a lip care product, a lipstick pencil or a lip gloss.   23. A composition according to any one of claims 1 to 22 which is a liquid.   24. A method for making up and / or caring for the skin and / or lips comprising the step of applying at least a composition according to any one of claims 1 to 23 on the skin and / or lips.