EP4267089A1

EP4267089A1 - Make-up composition with gloss and lasting properties

Info

Publication number: EP4267089A1
Application number: EP21852054.2A
Authority: EP
Inventors: Elodie CHAMPREDONDE; Valérie BOUCHARD DE LA POTERIE
Original assignee: LVMH Recherche GIE
Current assignee: LVMH Recherche GIE
Priority date: 2020-12-23
Filing date: 2021-12-23
Publication date: 2023-11-01
Also published as: US20240091114A1; FR3117859A1; JP2024503587A; CN116710057A; KR20230124025A; WO2022136809A1

Abstract

The present invention relates to a homogeneous cosmetic composition for make-up of keratin materials, in particular the lips, comprising, in a physiologically acceptable medium, at least: - one or more, linear or branched, C8-C19 alkanes; - one or more phenyl silicone oils, the refractive index of which at 25°C is greater than 1.45, preferably greater than 1.47; - a silicone-polyurethane polymer; - and optionally, in addition, at least one pigment.

Description

DESCRIPTION

TITLE: Makeup composition with hold and shine

FIELD OF THE INVENTION

The present invention relates to the cosmetics field and in particular to cosmetic compositions for making up keratin materials, in particular the lips.

STATE OF THE ART

Current lip make-up products are often categorized into products with good color retention or gloss products. For a double effect of color hold and shine, the products generally come in the form of a combination of formulas requiring a double gesture to obtain a film having the desired properties, with a first base formula otherwise called 'base coat' applied to the lips to provide color and hold, and a second formula to apply to the first, otherwise called 'top coat', generally colorless and providing a shiny film.

But there remains the need to develop products that can be applied in a single gesture, having both the performance of color retention and the performance of shine and which are homogeneous (homogeneous color). In addition to the simplicity of use, the application in a single gesture also allows for a thinner film (a single layer on the lips, therefore less material deposited).

The Applicant has precisely developed a homogeneous one-step composition making it possible to meet this expectation, by combining a silicone-polyurethane polymer, one or more linear or branched C8-C19 alkanes and one or more phenyl silicone oils.

This association allows to have an immediate shine superior or equal to the products on the market, an improved shine hold over time, a product with a unique gesture, and macroscopically homogeneous.

This composition is advantageous as a make-up composition for keratin materials, in particular the lips. DISCLOSURE OF THE INVENTION

A first aspect of the invention is therefore a homogeneous cosmetic composition for caring for and/or making up keratin materials, in particular the lips, comprising, in a physiologically acceptable medium, at least:

- one or more linear or branched C8-C19 alkane(s),

- one or more phenyl silicone oil(s), whose refractive index at 25° C is greater than 1.45, preferably greater than or equal to 1.47,

- a silicone-polyurethane polymer,

- And optionally additionally at least one pigment.

By “keratinous materials” is meant in particular the skin and/or the lips, the hair, the eyelashes and the nails. According to a particular mode, the composition of the invention is applied to the lips.

The invention also relates to a cosmetic process for caring for and/or making up keratin materials, in particular the lips, comprising the application, to said keratin materials, in particular the lips, of a composition according to the invention.

DETAILED DESCRIPTION OF THE INVENTION

Thus, a first aspect of the invention is therefore a homogeneous cosmetic composition for caring for and/or making up keratin materials, in particular the lips, comprising, in a physiologically acceptable medium, at least:

- one or more linear or branched C8-C19 alkane(s),

- a silicone-polyurethane polymer,

- And optionally additionally at least one pigment.

By 'homogeneous', it is meant that the composition of the invention has a visually homogeneous appearance, that is to say that each of the phases cannot be individualized with the naked eye in the composition which thus seems only consist of a single phase.

According to a particular embodiment, the oily phase in which the silicone-polyurethane polymer is dissolved comprises total contents of alkane oil(s) and respectively of phenyl silicone oil(s), such as the solution oily after mixing and incorporation of the silicone-polyurethane polymer either translucent or transparent. We will speak of 'mixture of alkanes/phenylated silicone oils/silicone-polyurethane polymer capable of forming a translucent or transparent oily solution or 'translucent or translucent ternary mixture'.

By 'translucent or transparent oily solution' or 'translucent or transparent ternary mixture', it is meant that the solution or mixture is not cloudy or opaque, and allows light to pass through and shows the objects behind it sharply.

According to a particular embodiment, the mixture comprises isododecane (branched alkane), a trimethyl pentaphenyl trisiloxane (and optionally a dipenylsiloxy phenyl trimethicone) and a silicone-polyurethane polymer in defined proportions for obtaining a translucent oily solution or transparent, leading to the obtaining of a homogeneous composition after addition of the other ingredients of the composition.

A person skilled in the art expert in the cosmetics field will thus define the optimal contents of each of the compounds of the ternary mixture according to his knowledge of the characteristics specific to each compound (in particular solubility, molecular weight) and its behavior in a binary alkane/phenyl silicone oil mixture then ternary alkane/phenyl silicone oil/polymer, to obtain a translucent or transparent oily solution.

According to a particular and preferred embodiment, the composition of the invention is an anhydrous composition.

The term “anhydrous” means in particular that the water is preferably not added to the compositions but may be present in trace form in the various compounds used in the compositions. In particular, the composition according to the invention comprises less than 4% by weight of water, preferably less than 3%, preferably less than 2%, more preferably less than 1%, even more preferably less than 0.5% by weight of water, relative to the total weight of said composition, or even is completely free of water.

According to a particular and preferred mode, the composition of the invention is a liquid and anhydrous composition.

The composition of the invention is a brilliant composition.

In particular, the gloss value of a deposit of a cosmetic composition is in particular measured using a gloss meter and expressed in gloss units (BU). Reference will be made indiscriminately to the gloss value of the composition or to the gloss value of the deposit on the skin or the lips. The gloss value of a composition can in particular be measured according to the following protocol. To measure the gloss of a product to be tested, a light ray of constant intensity is directed at a determined angle onto the surface to be tested, then the quantity of light reflected at the same angle is measured. This specular reflection is measured using a glossmeter. Depending on the gloss level, different reflection angles are used.

The gloss measurement is based on the amount of light reflected off a surface relative to a polished glass reference standard; it is expressed in Brilliant Units (BU).

The measurement is normalized with respect to an internal standard and reduced to a value out of 100: For this standard standard, the measurement value is fixed at 100 gloss units (calibration).

The closer the measured value is to 100, the brighter the sample.

The amount of light reflected on the surface depends on the angle of incidence and the properties of the surface itself.

The gloss level is divided into three categories: matte (gloss value below 10UB), semi-gloss (gloss value between 10 and 70UB) or high gloss (gloss value above 70UB). To determine the appropriate measurement angle, a glossmeter with an angle of incidence of 60° is used.

In the context of the present invention, the gloss value of the composition is generally greater than 70UB, in particular greater than or equal to 75UB, or even greater than or equal to 80UB.

In addition, the composition of the invention is advantageously a one-step composition, to provide color, shine and hold.

The composition of the invention also comprises a silicone-polyurethane polymer as defined below. According to a particular embodiment, the composition of the invention comprises a silicone-polyurethane polymer with an active matter content (dry matter) ranging from 14 to 25%, preferably from 16 to 20%, by weight relative to the total weight of the composition.

Silicone-polyurethane polymer By “silicone-polyurethane polymer” according to the invention, is meant any polymer comprising organosiloxane units and urethane bonds.

According to a particular embodiment, the silicone-polyurethane polymer according to the invention is the reaction product of a polyorganosiloxane functionalized with hydroxyl groups, preferably comprising at least two hydroxyl groups, with a diisocyanate compound.

Such a polyorganosiloxane functionalized with hydroxyl groups corresponds to the formula formula (I)

[Cheml ] in which R is chosen independently at each occurrence from a hydrogen atom, a hydroxyl group, and optionally substituted hydrocarbon groups containing from 1 to 10 carbon atoms, and in particular from an alkyl, alkenyl, alkynyl, aryl, aryl group -alkyl or alkyl-aryl substituted or not; preferably, R is selected from linear, cyclic or branched and optionally substituted C1-C6 alkyl or alkenyl groups, including, without limitation, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, amyl groups , hexyl, cyclohexyl, vinyl, C1-C8 allyl or aryl, aryl-alkyl or alkyl-aryl, including, without limitation, phenyl, benzyl, tolyl, xylyl, wherein each of the above R groups may be substituted by optionally by one or more heteroatoms, including oxygen, nitrogen, phosphorus and halogen, especially fluorine, as exemplified by fluoroalkyl (perfluoroalkyl) groups such as mono-, di- and tri fluoromethyl, perfluorophenyl, and substituted C1-C6 alkyl amino groups, including those of the formula - (CH ₂ )I. ₆ -NR ^N ₂ and - (CH ₂ )I-6-NR ^N - (CH ₂ )I-6-NR ^N 2 WHERE R ^N is typically hydrogen, but can also be methyl, ethyl, propyl , and the like; polyether groups, including, without limitation, polyethylene oxide groups having the formula -(CH ₂ CH ₂ O) _n -, propylene oxide groups having the formula -(CH(CH ₃ ) CH ₂ O) _n - and combinations thereof; and amine oxide, phosphate, hydroxyl, ester and/or carboxylate functions, or the like; Where wherein R may include an additional -L-OH group; wherein L represents either a bond or a linking group; preferably L is a linking group selected from divalent hydrocarbons having 1 to 10 carbon atoms, including an alkyl, alkenyl, alkynyl, aryl, alkyl-aryl or divalent aryl-alkyl group, such as for example an alkyl group in C1 -C10, including, without limitation, divalent groups of the formula -(CH ₂ )II ₀ -, preferably -(CH ₂ )I- 6-, and more preferably L is -CH2CH2CH2-; and where n is an integer between 0 and 5000, preferably between 1 and 200, more preferably between 10 and 100, and even more preferably between 10 and 50.

Preferably, R represents at least one or more occurrences of a methyl group, more preferably, R represents a methyl group at all or almost all of the occurrences, which means that R represents a methyl group at more than 90 % of occurrences, in particular at more than 95% of occurrences, or even at more than 98% of occurrences. According to one embodiment of the invention, the polyorganosiloxane functionalized with hydroxyl groups comprises a polymethylsiloxane corresponding for example to the structure of formula la:

[Chem2] in which L and n are as previously defined.

According to a preferred embodiment of the invention, the polyorganosiloxane functionalized with hydroxyl groups comprises a polymethylsiloxane corresponding for example to the structure of formula Ib:

[Chem3] where n is as defined above.

The diisocyanate may in particular correspond to the formula O=C=NR ¹ -N=C=O, where R ¹ is a divalent hydrocarbon group containing from 1 to 20 carbon atoms, including 20 optionally substituted by one or more heteroatoms, and in particular R ¹ can be selected from a linear, cyclic or branched, optionally substituted cyclic alkyl, alkenyl, alkynyl, aryl, alkyl-aryl or arylalkyl group, including, without limitation: i. a group of formula: [Chem-4] ii. a group of formula: [Chem5] iii. a group of formula: [Chemô] iv. a group of formula: [Chem7] v. a group of formula: [Chem8] and combinations thereof.

Diisocyanates that may be suitable within the scope of the invention include, without limitation, toluene diisocyanate; methylene diphenyl diisocyanate, including 2,2'-MDI, 2,4'-MDI and 4,4'-MDI; 1,6-hexamethylene diisocyanate; isophorone diisocyanate; dicyclohexylmethane-4,4'-diisocyanate; xylene diisocyanate; cyclohexane diisocyanate; 3,3'-dimethyl-4,4'-diphenylmethane diisocyanate; p-phenylene diisocyanate; m-phenylene diisocyanate; 4,4'-isopropylidene dicyclohexyl isocyanate; and their equivalents.

In a preferred embodiment, the diisocyanate is selected from the group consisting of 1,6-hexamethylene diisocyanate, dicyclohexylmethane-4,4'-diisocyanate, isophorone diisocyanate, and combinations thereof.

In one embodiment, the diisocyanate comprises or consists essentially of 1,6-hexamethylene diisocyanate.

In another embodiment, the diisocyanate comprises or consists essentially of isophorone diisocyanate.

In yet another embodiment, the diisocyanate comprises or consists essentially of dicyclohexylmethane-4,4'-diisocyanate, which embodiment is particularly preferred.

Thus, according to a particular embodiment, the silicone-polyurethane polymer is the reaction product of a polyorganopolysiloxane functionalized with hydroxyl groups, in particular having the structure of formula (I)

[Chem3] in which n is an integer between 0 and 5000, preferably between 1 and 200, more preferably between 10 and 100, and even more preferably between 10 and 50, with a diisocyanate compound, in particular chosen from the group consisting of diisocyanate 1,6-hexamethylene, dicyclohexylmethane-4,4'-diisocyanate, isophorone diisocyanate, and combinations thereof.

According to a preferred embodiment, the silicone-polyurethane polymer according to the invention comprises recurring units derived from the polyorganosiloxane functionalized with hydroxyl groups and from the diisocyanate in the form of an alternating copolymer AB, where the unit A has the structure of formula II: wherein R, L and n are defined as above in relation to formula I, la, Ib and le, and wherein unit B has the structure of formula III:

[Chem 0] where R1 is as previously defined, and in which the units A and B are arranged according to a linear, branched or cyclic configuration, and preferably linear.

The polymer may also include branching or grafting points in the polyorganosiloxane wherein one or more R groups in formula I or II is a group IV such that:

[Chem11 ] wherein R is as defined for formula I, and R* may represent a -LO- group further coupling the side chain of a B unit of formula III, which may in turn be further coupled to the unit A of formula II, and so on, or else R* can represent -L-OH, an R group as previously defined, or a terminal group.

When the polyorganosiloxane has such branching or grafting points, they may be present as T- or Q-type grafts, where T indicates that only an R group on the Si atom is a polyorganosiloxane chain, as shown below. above and Q. indicates that both R groups are polyorganosiloxanes.

These types of polyorganosiloxane compounds are called copolymer of silicone-polyurethane polymer and T-resin or Q-resin, branched or grafted.

Silicone-polyurethane polymers can also be prepared from functionalized isocyanate prepolymers. For example, an isocyanate prepolymer can be a difunctional or multifunctional polyorganosiloxane isocyanate, such as the polyorganosiloxane diisocyanate shown below in Formula V: in which R, R ¹ and L are as defined previously, and in which x is an integer between 0 and 5000, preferably between 1 and 200, more preferably between 10 and 100, and more preferably still 10 and 50.

The prepolymer can also be multifunctional by introducing additional isocyanate groups carrying one or more R groups. The functionalized isocyanate prepolymer is reacted with a polyorganosiloxane functionalized by hydroxyl groups to obtain a compound of formula I or a multifunctional analogue of this one.

The prepolymer according to formula V generally has a molecular weight ranging from 4,000 to about 15,000 Daltons. The prepolymer according to formulas I, Ia, Ib and typically has a molecular weight ranging from 250 to about 15,000 Daltons.

In one embodiment of the invention, the silicone-polyurethane polymer is free or substantially free of polyalkylene glycol subunits, especially polyethylene glycol (PEG) or polypropylene glycol (PPG). By "essentially free of", it is meant that the polymer comprises less than about 1% by weight, preferably less than about 0.5% by weight, and more preferably less than about 0.1% by 20% by weight of polyalkylene glycol subunits.

In a preferred embodiment, the silicone-polyurethane polymer used in the cosmetic compositions of the invention is a linear polymer comprising the reaction product of formula Ib with a diisocyanate chosen from the group consisting of the diisocyanate of 1, 6-hexamethylene, dicyclohexylmethane-4,4'-diisocyanate, isophorone diisocyanate, and combinations thereof.

Such a silicone-polyurethane polymer is for example available from Siltech Corporation in the form of a premix in isododecane, under the commercial reference SILMER UR 5050 (45% by dry matter of polymer in isododecane).

According to another embodiment, a silicone-polyurethane polymer is used in the form of a premix in a hemi-squalane.

According to another embodiment, a silicone-polyurethane polymer is used in the form of a premix in a linear C9-C16 alkane or a mixture of linear C9-C16 alkanes, preferably a mixture of n -nonane and n-dodecane (C9-C12, VEGELIGHT SILK) or a mixture of n-undecane and n-tridecane (C11 -C13, CETIOL ULTIAAATE).

According to a particular mode, the silicone-polyurethane polymer according to the invention will be present in the composition of the invention in a content ranging from 14 to 25% by weight of active matter (dry matter) of polymer, preferably from 16 to 20% by weight of active polymer material relative to the total weight of the composition.

Oil phase

The oily phase of the composition of the invention comprises at least one or more linear or branched C8-C19 alkanes and one or more phenyl silicone oils having a refractive index of at least 1.45, preferably at least 1, 47, in particular whose refractive index at 25° C. is greater than 1.45, preferably greater than or equal to 1.47.

The Applicant has demonstrated, as illustrated in the examples, the role of volatile hydrocarbon oils, in particular linear or branched C8-C19 alkanes in the formulation of the composition of the invention and in particular the solubilization of the silicone polymer polyurethane and the incorporation of phenyl silicone oil to obtain a homogeneous composition. These linear or branched C8-C19 alkanes, used in a content defined with respect to the active material content of the silicone-polyurethane polymer, in fact make it possible to properly disperse the said silicone-polyurethane polymer and thus facilitate its mixing with the other ingredients of the composition and in particular the phenyl silicone oil with a refractive index greater than 1.45.

Volatile hydrocarbon oil (linear and branched C8-C19 alkanes)

By 'oil', we mean a liquid fatty substance at 25°C and atmospheric pressure.

By 'hydrocarbon oil' is meant an oil comprising mainly carbon and hydrogen atoms and optionally one or more functions chosen from hydroxyl, ester, ether, carboxylic functions. These oils are in particular free of —Si—O— groups.

By 'volatile oil' according to the invention is meant an oil having lost more than 20% by mass of its mass at 15 minutes, more than 40% by mass of its mass at 30 minutes and more than 70% by mass of its mass at 60 minutes, according to the following protocol:

20mg of the oil to be studied is weighed on a 5cm x 5cm PMAAA plate using a micropipette and a precision balance. This material is spread with the finger over the entire plate. Then, it is placed in a ventilated enclosure thermostated at 25° C and 50% humidity. For each material, the test is carried out 3 times. The mass loss during drying is measured after 15 minutes, 30 minutes and 60 minutes. The lost mass is expressed according to the following calculation:

[Math.1 ]

% mass lost 1.00

With m _tx corresponding to the mass remaining at the measured time (t15min, t30min or tôOmin) and mto corresponding to the mass initially applied.

The volatile hydrocarbon-based oil is preferably chosen from linear or branched alkanes comprising from 8 to 19 carbon atoms and mixtures thereof.

As linear or branched C8-C19 alkanes, mention may be made in particular of:

- C8-C16 iso-alkanes (also called isoparaffins) such as isododecane, isodecane, isohexadecane, hemi-squalane and, for example, the oils sold under the trade names ISOPAR® or PERMETYL ®, - linear alkanes having respectively hydrocarbon chains in

- C9-C17, C10-C14, such as a mixture of undecane and tridecane, marketed by BASF Care Créations under the name Cetiol® Ultimate,

- C15-C19, such as those marketed by Seppic under the name EMOGREEN® L15,

- C9-C12, C12-C14, such as those marketed by BIOSYNTHIS under the name VEGELIGHT® SILK (INCI name C9-12 ALKANE), VEGELIGHT® 1214LC,

- n-dodecane (C12) and n-tetradecane (C14), in particular sold by Sasol respectively under the references PARAFOL® 12-97 and PARAFOL® 14-97,

- and mixtures thereof.

Thus, according to a particular embodiment, the branched C8-C19 alkanes are chosen from the group consisting of isododecane, isodecane, isohexadecane, hemi-squalane and mixtures thereof, preferably isododecane, hemi-squalane and the linear C8-C19 alkanes are chosen from the group consisting of n-dodecane, n-undecane, n-tridecane, n-tetradecane, n-pentadecane and mixtures thereof.

According to a particular embodiment, the composition comprises at least isododecane as branched C8-C19 alkane.

The total content of linear or branched alkanes makes it possible to dissolve the polyurethane silicone polymer and the phenyl silicone oil(s) of the composition, so that the homogeneous composition obtained allows the application of a film on the lips, which has particularly remarkable hold and shine properties.

According to a particular embodiment, the content of linear or branched C8-C19 alkanes in the composition of the invention will be at least 20% by weight relative to the total weight of the composition. In particular, it will in particular range from 20 to 60% by weight, in particular from 25 to 45% by weight, and even more particularly from 30 to 40% by weight relative to the total weight of the composition.

Phenyl silicone oil(s)

The term “silicone oil” is understood to mean, according to the invention, an oil comprising at least one silicon atom, and in particular at least one Si—O group. The term “phenyl silicone oil” according to the invention is understood to mean an organopolysiloxane substituted with at least one phenyl group.

As phenyl silicone oils having a refractive index of at least 1.45, in particular a refractive index at 25° C. greater than 1.45, preferably greater than or equal to 1.47, which can be used in the composition of the invention, mention may be made in particular of the oils with the INCI name phenylpropyldimethylsiloxysilicate, diphenyl dimethicone, diphenylsiloxyphenyltrimethicone, trimethyl pentaphenyl trisiloxane, phenyltrimethicone, Trimethylsiloxyphenyl dimethicone, and mixtures thereof.

The following references can be cited in particular: [Table 1]

"according to the supplier sheets

According to a particular embodiment of the invention, the composition comprises at least one phenyl silicone oil with a refractive index greater than 1.50, or even greater than or equal to 1.55. Thus, according to a particular embodiment, the composition of the invention comprises one or more phenyl silicone oil(s) with a refractive index ranging from 1.46 to 1.50 (eg diphenyl dimethicone, diphenylsiloxyphenyltrimethicone , Trimethylsiloxyphenyl dimethicone) and one or more phenyl silicone oil(s) with a refractive index greater than 1.50, in particular greater than 1.55 (eg Trimethyl pentaphenyl trisiloxane).

According to a particular embodiment of the invention, the composition comprises at least one phenyl silicone oil having a viscosity at 25° C. of greater than 100 mPa.s. According to a particular and preferred embodiment, this phenyl silicone oil has a viscosity ranging in particular from 120 mPa.s to 1500 mPa.s, and preferably from 150 m Pa.s to 1100 m Pa.s. Such an oil can be called a shiny oil.

Mention may in particular be made of BELSIL PDM 1000 from the company WACKER, phenyl silicone oils, such as those identified by the INCI name phenyl trimethicone, an example of which consists of the silicone available under the trade name MIRASIL PTAA from the company RHODIA , those identified by the INCI name phenylpropyldimethylsiloxysilicate, an example of which consists of the silicone available under the trade name SILSHINE 151 from GENERAL ELECTRIC and those identified by the INCI name trimethyl pentaphenyl trisiloxane, an example of which consists of the silicone available under the trade name DC PH 1555 HRI from the company DOW CORNING, - and mixtures thereof.

Thus, the composition may preferably comprise a phenyl silicone oil of formula (VI)

[Chem13] in which Me represents a methyl and Ph represents a phenyl, otherwise called tri methyl pentaphenyl trisiloxane.

Such a phenyl silicone is in particular manufactured by Dow Corning under the reference PH-1555 HRI or even Dow Corning 555 Cosmetic Fluid (chemical name: 1,3,5-trimethyl 1,1,3,5,5-pentaphenyl trisiloxane, INCI name : trimethylpentaphenyl trisiloxane). Dow Corning 554 Cosmetic Fluid can also be used. According to a preferred mode, the reference PH-1555 HRI (INCI name: trimethyl pentaphenyl trisiloxane) will be used. According to another particular embodiment, the composition of the invention comprises at least one phenyl silicone oil of formula (VII)

[Chem14] in which

Me is methyl and Ph is phenyl, OR' represents a group - OSiMe3 y varies between 1 and 1000, and z varies between 1 and 1000.

It is possible to use, for example, Belsils PDM20, PDM100 and PDM1000 from Wacker and in particular trimethyl siloxyphenyl dimethicone, in particular sold under the name BELSIL PDM 1000 marketed by the company Wacker.

According to yet another particular mode, the phenyl silicone oil is an oil of formula (VIII)

[Chem15] in which the R groups represent, independently of each other, a -SiO(CH ₃ )3 group, a methyl or a phenyl, the total number of phenyl being at least equal to 2, preferably equal to 3.

Mention may in particular be made of the oil marketed under the names KF50, KF53, K54 and KF56 from Shin Etsu, preferably the reference KF56 with the INCI name dipenylsiloxy phenyl trimethicone, the formula of which is as follows:

[Chem16]

According to a particular and preferred mode, the composition of the invention will comprise two phenyl silicone oils.

Thus, according to a particular mode, the composition of the invention may comprise at least one trimethyl pentaphenyl trisiloxane, and optionally in addition one diphenylsiloxy phenyl trimethicone.

According to a particular embodiment, the total content of phenylated silicone oil(s) in the composition of the invention will in particular range from 5 to 50% by weight, in particular from 8 to 30% by weight with respect to the total weight of the composition.

Those skilled in the art will be able to adjust the contents of phenyl silicone oil(s) in the ternary mixture described above and consisting of linear or branched C8-C19 alkanes/phenyl silicone oils with a refractive index of at least 1.45/silicone-polyurethane polymer, to obtain a translucent or transparent ternary mixture.

Additional compounds

According to a particular and preferred embodiment, the composition may also comprise a copolymer comprising carboxylate groups and polydimethylsiloxane groups, to further improve the gloss of the composition.

By "copolymer comprising carboxylate groups and polydimethylsiloxane groups", is meant according to the invention a copolymer resulting from the polymerization (a) of one or more carboxylic monomer(s) (acid or ester), with (b ) one or more polydimethylsiloxane (PDMS) chain(s) comprising at least one polymerizable radical.

Among the “carboxylic monomers” suitable for implementing the invention, mention may be made of carboxylic acid monomers and carboxylic acid ester monomers. According to one embodiment of the invention, the monomers in the form of esters can be chosen from linear or branched alkyl acrylates and/or methacrylates, preferably C1-C24 and better still C1-C22, the alkyl radical being chosen from methyl, ethyl, stearyl, butyl, ethyl-2-hexyl radicals, and mixtures thereof.

According to one embodiment of the invention, the copolymer may comprise, as carboxylate groups, at least one group chosen from acrylic acid, methacrylic acid, acrylates or methacrylates of methyl, ethyl, stearyl, butyl , ethyl-2-hexyl, and mixtures thereof.

By “polydimethylsiloxanes” (also called organopolysiloxanes or, in abbreviation, PDMS), is meant any organosilicon polymer or oligomer with a linear structure, of variable molecular weight, obtained by polymerization and/or polycondensation of suitably functionalized silanes, and constituted, for the essential, by a repetition of main units in which the silicon atoms are linked together by oxygen atoms (siloxane bond =Si-O-Si=), comprising trimethyl radicals directly linked via an atom of carbon on said silicon atoms.

The copolymers which can be used in the composition of the invention can be obtained according to the usual polymerization and grafting methods, for example by radical polymerization (a) of a PDMS comprising at least one polymerizable radical group (for example on one of the ends of the chain or on both) and (b) of at least one carboxylic monomer, as described for example in documents US-A-5,061,481 and US-A-5,219,560. The copolymers obtained can have a molecular weight ranging from approximately 3000 g/mol to approximately 200,000 g/mol and in particular from approximately 5000 g/mol to approximately 100,000 g/mol.

A copolymer that can be used in a composition of the invention can be present as it is, or in the form dispersed in a solvent, such as lower alcohols comprising from 2 to 8 carbon atoms, such as isopropyl alcohol, or oils such as volatile silicones (eg dimethicone).

As copolymers which can be used in a composition of the invention, mention may be made, for example, of copolymers of acrylic acid and of stearyl acrylate with polydimethylsiloxane grafts, copolymers of stearyl methacrylate with polydimethylsiloxane grafts, copolymers of acrylic acid and stearyl methacrylate with polydimethylsiloxane grafts, copolymers of methyl methacrylate, butyl methacrylate, ethyl-2-hexyl acrylate and stearyl methacrylate with polydimethylsiloxane grafts. Mention may also be made, as a copolymer which can be used in the composition of the invention, of the copolymers marketed by the company SHIN-ETSU under the names KP-561 (CTFA name: acrylates/dimethicone), KP-541 where the copolymer is dispersed at 60% by weight in isopropyl alcohol (CTFA name: acrylates/dimethicone and Isopropyl alcohol), the acrylate/dimethicone copolymers in methyl trimethicone (such as, for example, KP-549 and KP-579 from Shin-Etsu), and acrylate/dimethicone copolymers in isododecane (such as, for example, KP-550 from Shin-Etsu).

According to a particular and preferred embodiment of the invention, a copolymer of acrylate and dimethicone is used comprising a C18-C22 alkyl chain, such as Acrylates/stearyl acrylate/dimethicone methacrylate (KP-561 P from Shin Etsu) and Acrylates/behenyl acrylate/dimethicone methacrylate (KP562P from Shin Etsu), preferably KP-561 P which is in waxy form (melting point of approximately 40° C.).

The content of copolymer comprising carboxylate groups and polydimethylsiloxane groups in the composition of the invention will in particular range from 0 to 20% by weight, in particular from 2 to 15% by weight relative to the total weight of the composition.

According to a particular mode of the invention, the composition of the invention will comprise: isododecane, preferably in a content ranging from 25 to 45% by weight relative to the total weight of the composition, a trimethyl pentaphenyl trisiloxane and optionally in addition a diphenylsiloxy phenyl trimethicone, preferably in respective contents ranging from 5 to 15% by weight and from 5 to 15% by weight relative to the total weight of the composition, and a silicone-polyurethane polymer reaction product a functionalized polyorganosiloxane by hydroxyl groups of formula Ib: where n is as defined above with a methylene diphenyl diisocyanate, in particular in a content of 16 to 25% by weight of active material (dry matter) relative to the total weight of the composition,

- And advantageously in addition a copolymer comprising carboxylate groups and polydimethylsiloxane groups. Other additional oils

The invention may also comprise other silicone or hydrocarbon oils, distinct from the oils described above, to provide lightness and hold to the film deposited on the skin or comfort.

Mention may in particular be made of ester oils, such as fatty acid esters, in particular of 4 to 22 carbon atoms, synthetic esters such as oils of formula R1COOR2 in which Ri represents the residue of a linear fatty acid or branched chain containing from 4 to 40 carbon atoms and R ₂ represents a hydrocarbon chain in particular branched containing from 4 to 40 carbon atoms provided that R1+R2 is >16, the hydroxylated esters, preferably having a total carbon number ranging from 35 to 70, fatty alcohol or branched fatty acid esters C24-C28, and mixtures thereof, preferably hydroxylated esters such as polyglycerol-2 triisostearate, diisostearyl malate, and mixtures thereof.

Ester oils are particularly useful as a dispersant for pigments, in particular for pigments which include a surface treatment with a hydrophobic hydrocarbon compound aimed at giving these pigments an affinity for the fatty phase of the composition. The oil dispersing these treated pigments improves the homogeneity of the composition according to the invention and that of the film applied to the lips. The visual aspect is thus greatly improved.

The fatty phase of the composition of the invention is generally textured or structured by a gelling and/or texturizing agent, in particular a lipophilic gelling agent, a wax, a pasty fatty substance, or mixtures thereof.

According to a particular mode, the composition of the invention comprises at least one lipophilic gelling agent.

gelling agents

As lipophilic gelling agent, mention may in particular be made of mineral gelling agents such as bentones dispersed in an oil. Mention may be made, for example, of the reference BENTONE GEL ISD V from Elementis with the INCI name Isododecane (and) Disteardimonium Hectorite (and) Propylene Carbonate.

Thus, according to a particular mode, the composition of the invention also comprises a lipophilic gelling agent, in particular a mineral gelling agent, preferably a bentone. Other lipophilic gelling agents can be used in the composition of the invention if they still make it possible to obtain a solution as defined previously.

The total content of lipophilic gelling agent(s) may range from 0.1 to 5%, in particular from 0.5 to 3% by weight relative to the total weight of the composition.

Thus, according to a particular mode of the invention, the composition of the invention will comprise: isododecane, preferably in a content ranging from 25 to 45% by weight relative to the total weight of the composition, a trimethyl pentaphenyl trisiloxane and optionally additionally a diphenylsiloxy phenyl trimethicone, preferably in respective contents ranging from 5 to 15% by weight and from 5 to 15% by weight relative to the total weight of the composition, and a silicone-polyurethane polymer reaction product a polyorganosiloxane functionalized with hydroxyl groups of formula Ib: where n is as defined above with a methylene diphenyl diisocyanate, in particular in a content of 16 to 25% by weight of active material (dry matter) relative to the total weight of the composition, a lipophilic gelling agent of the bentone type ( INCI name Disteardimonium Hectorite), preferably in a content ranging from 0.1 to 5%, relative to the total weight of the composition;

- And advantageously in addition a copolymer comprising carboxylate groups and polydimethylsiloxane groups.

The composition according to the invention may also further comprise an ingredient chosen from a wax, a filler, a dyestuff and mixtures thereof.

Raincoats By wax, within the meaning of the present invention, is meant a compound which is solid at 25° C. and which exhibits a reversible solid/liquid state change and a melting temperature above 30° C., preferably above 45° C.

Mention may be made of natural waxes (sunflower wax, berry wax), microcrystalline waxes, paraffin waxes, polyethylene waxes, ozokerite, carnauba wax, beeswax, and mixtures thereof.

Thus, according to a particular and preferred mode, the composition of the invention will also comprise at least one wax, making it possible to stabilize, or even to freeze the system without disturbing the result of hold and shine.

A composition according to the invention may comprise a wax content ranging from 0.5% to 10%, for example from 1% to 5% by weight, relative to the total weight of the composition.

According to a particular embodiment, the composition of the invention further comprises an additional ingredient chosen from fillers, coloring materials, and mixtures thereof.

Expenses

In addition, the composition of the invention may advantageously include fillers to provide comfort and prevent the possible appearance of stickiness linked to the high level of polymer held in the composition.

Within the meaning of the invention, by "fillers" is meant particles of any shape, colorless or white, of mineral or organic, natural or synthetic nature, which are in a form (platelet, spherical or oblong), insoluble and dispersed in the middle of the composition. The fillers are chosen in particular from silicas, micas, of natural or synthetic origin, kaolin, zinc and titanium oxides; calcium carbonate, magnesium carbonate and hydrocarbonate; zinc, magnesium or lithium stearate, zinc laurate, magnesium myristate; synthetic polymer powders, such as polyethylene, polyesters, polyamides (for example nylon); polyacrylic or polymethacrylic acid powders, silicone or silicone resin powders; cellulose powders; mineral powders such as spherical silica; spherical titanium dioxides; glass and ceramic beads; powders of organic materials of natural origin such as crosslinked or non-crosslinked corn, wheat, rice, cotton starches, and mixtures thereof. As preferred fillers, mention may in particular be made of silica powders, cellulose powders, cotton powders, and mixtures thereof.

The fillers may be present in a content ranging from 2 to 10%, in particular from 3 to 8% by weight relative to the total weight of the composition.

A composition of the invention is in particular a makeup composition comprising at least one dyestuff.

Dyestuffs

By dyestuff is meant within the meaning of the present invention, a compound capable of producing a colored optical effect when it is formulated in sufficient quantity in an appropriate cosmetic medium.

A dyestuff can be chosen from organic or inorganic dyestuffs, optical effect materials, and mixtures thereof, soluble or insoluble in the continuous phase of the invention, in this case the oily phase of the invention.

According to a particular embodiment, the dyestuff(s) are chosen in particular from mineral pigments, organic pigments, and mixtures thereof.

By “pigments” is meant white or colored, mineral or organic particles, insoluble in an aqueous solution, intended to color and/or opacify the resulting deposit. Mention may be made of inorganic pigments, organic pigments, and composite pigments (that is to say pigments based on inorganic and/or organic materials).

Among the “mineral pigments”, mention may be made, by way of examples, of titanium dioxide (rutile or anatase), optionally surface-treated; black, yellow, red and brown iron oxides; manganese violet; ultramarine blue chromium oxide hydrated chromium oxide and ferric blue.

For compositions intended for the lips, mention may be made, by way of examples, of titanium dioxide; black, yellow, red and brown iron oxides and manganese violet.

Among the "organic pigments", mention may be made, for example, of the pigments D & C red No. 19; D & C red No. 9; D a C Red No. 22; D a C Red No. 21; D a C Red No. 28; D a C Yellow No. 6; D a C Orange No. 4; D a C Orange No. 5; D to C Red No. 27; D to C red No. 13; D a C Red No. 7; D to C Red #6; D to C Yellow No. 5; D a C Red No. 36;; D a C Red No. 33; D to C orange no. 10; D & C yellow No. 6; ; D a C Red No. 30; Ac red no. 3; D ac Blue 1; carbon black and lacquers.

In particular, the dyestuff(s) are present in the composition in a content ranging from 2% to 20% by weight, preferably from 3% to 15% by weight relative to the total weight of the composition.

GALENIC

The composition of the invention is a makeup and/or care composition for keratin materials, in particular a makeup and/or care composition for the skin and/or the lips, preferably the lips.

According to a first embodiment, the composition of the invention is a top-coat composition, which can be used on any makeup composition for the lips, to provide hold and shine.

According to another embodiment, the composition of the invention is a make-up composition in a single step, to provide color, shine and hold.

The composition of the invention is in particular a liquid composition, preferably for the lips.

In one embodiment of the invention, it can be in liquid form and be a fluid lipstick, a lip lacquer, a lip gloss (gloss in Anglo-Saxon terminology), a sunscreen or hair coloring product. skin, eyeshadow or eyeliner.

Preferably, the composition is a makeup composition for the lips, in particular in the form of a gloss.

COSMETIC PROCESS

The invention also relates to a cosmetic process for caring for and/or making up keratin materials comprising the application, to said keratin materials, in particular the skin and/or the lips, preferably the lips, of a composition according to 'invention.

The composition applied to the lips is preferably a liquid makeup composition for the lips, in particular a fluid lipstick, a lip lacquer or a gloss. The process according to the invention is in particular a process for making up the lips, intended to deposit on the said lips, in a single gesture, a glossy and long-lasting film of shine and color.

The invention will now be illustrated in the following non-limiting examples. The % are expressed in % by weight relative to the total weight of the composition, unless otherwise indicated.

EXAMPLES

Example 1: solubility tests

Solubility tests are carried out for various mixtures comprising the polyurethane silicone polymer, a volatile hydrocarbon oil and at least one phenyl silicone oil. The ratios for which a clear and transparent solution is obtained are those which are suitable for the invention. In this case, the compounds of the mixture form a single and unique phase. If the ratios of the compounds in the mixture do not make it possible to obtain a clear oil phase, an opacity of the mixture is observed, meaning that the compounds are immiscible at the ratios tested.

For these tests, SILMER UR1550 is used, which comprises the silicone polyurethane polymer (I NCI= Bis-Hydroxypropyl Dimethicone/SMDI Copolymer) dispersed in isododecane, at 45% by dry weight of polymer.

Depending on the ratio tested, an additional quantity of the ingredient is added.

1 - Mixtures (with 1 phenyl silicone oil with viscosity > 150mPa.s at 25°C): Bis-Hydroxypropyl Dimethicone/SMDI Copolymer / Isododecane / Trimethyl Pentaphenyl Trisiloxane (DOW CORNING PH-1555)

The blends below include 40% by weight of SILMER UR-1550, i.e. 18% by dry weight of polyurethane silicone polymer and 22% by weight of isododecane. The 18% of polyurethane silicone polymer is dispersed in 82% of a mixture of oils comprising an isododecane and a phenyl silicone oil with a viscosity of 160-190mPa.s at 25°C.

The results are included in Table 2 below:

[Table 2]

Observation of the appearance of the mixture:

Opaque= immiscible

Clear = miscible = OK for the invention

The results show that to obtain a clear mixture with 18% by weight of silicone polyurethane polymer, it is necessary, in the case of a phenyl silicone oil with a viscosity >100mPa.S at 25°C, a mixture of oils comprising 5 to 35% of phenyl silicone oil with a viscosity >150 mPa.s and 45 to 75% of C8-C19 alkanes, relative to the total weight of the mixture. In this case, the content of C8-C19 alkanes will be at least 1.5x greater than the said content of phenyl silicone oil with a viscosity >150 mPa.S at 25°C. We will speak more generally (by rounding up 18% to 20% silicone polyurethane polymer) of an 80 (oil)/20 silicone polyurethane polymer mixture, with a weight ratio of 5-35% phenyl silicone oil(s) ( s) of viscosity >100mPa.s/ 45-75% of C8-C19 alkanes/ 20% of silicone polyurethane polymer, i.e. a weight ratio of 1/3 phenyl silicone oil(s) of viscosity >100mPa.s and 2/3 of C8-C19 alkanes relative to the total weight of the oils in the mixture.

2 - Mixtures (with 2 phenyl silicone oils):

Bis-Hydroxypropyl Dimethicone/SMDI Copolymer/Isododecane/Trimethyl Pentaphenyl Trisiloxane (DOW CORNING PH-1555)/Diphenylsiloxyphenyltrimethicone (KF-56A) Results are included in Table 3 below [Table 3]

Observation of the appearance of the mixture:

Opaque^ immiscible Clear= miscible = OK for the invention

The results show that to obtain a clear mixture with 18% by weight of silicone polyurethane polymer, it is necessary, in the case of a combination of phenyl silicone oil with a viscosity >100mPa.s and phenyl silicone oil with a viscosity < 50mPa.s .s, a mixture of oils comprising 60% phenyl silicone oil(s) and 20% alkanes in

C8-C19, relative to the total weight of the mixture. In such a mixture, the content of low-viscosity phenyl silicone oil is higher than the content of high-viscosity phenyl silicone oil and the content of C8-C19 alkanes remains greater than or equal to the content of high-viscosity phenyl silicone oil. We will speak more generally (by rounding up 18% to 20% silicone polyurethane polymer) of an 80 (oil)/20 silicone polyurethane polymer mixture, with a weight ratio of 60% phenyl silicone oil(s)/20 % C8-C19 alkanes/ 20% polyurethane silicone polymer. The combination of a low viscosity phenyl silicone oil with a high viscosity phenyl silicone oil thus makes it possible to incorporate into the mixture oils a higher total content of phenyl silicone oils than in the previous example, for an even better shine result.

These results show that the low solubility of the polyurethane silicone polymer in the presence of phenyl silicone oil requires the addition of an excess of hydrocarbon oil (isododecane in the present examples) to obtain a clear solution.

Among the phenyl silicone oils tested, the presence of KF-56A in the mixture makes it possible to increase the total content of phenyl silicone oils and therefore the gloss result of the film.

Example 2: liquid lipstick

The composition below is a liquid lipstick according to the invention.

The percentages are expressed by weight relative to the final composition. [Table 4]

The composition is prepared according to the following procedure:

SILMER, KP 561 P and phase A oils are mixed under Rayneri at 70°C, until a clear mixture is obtained. The BENTO GEL is then added and the mixture is left to homogenize at 1500 revolutions/minute, for the necessary time.

The C-phase pigments are dispersed in the B-phase ester oils and ground. They are added as well as the wax to the previous phase. After cooling to less than 40° C., the silica filler is added to the preceding phase, and the mixture is left to homogenize for 5 minutes. The composition is a liquid and homogeneous lip product.

Applied to the lips, the composition makes it possible to obtain long-lasting and shiny make-up in a single gesture.

Example 3: Lipstick The composition below is a liquid lipstick according to the invention.

The percentages are expressed by weight relative to the final composition.

[Table 5]

The composition is prepared according to the following procedure:

The SILMER, the KP 561 P and the oils of phase A are mixed under Rayneri at 70° C., until a clear mixture is obtained. The BENTO GEL is then added and the mixture is left to homogenize at 1500 revolutions/minute, for the necessary time.

The C-phase pigments are dispersed in the B-phase ester oils and ground. They are added to phase A. The composition is then cooled to ambient temperature.

The composition is a liquid and homogeneous lip product.

Applied to the lips, the composition makes it possible to obtain a long-lasting and shiny make-up in a single gesture.

Example 4: lipstick

The composition below is a liquid lipstick according to the invention.

The percentages are expressed by weight relative to the final composition. [Table 6]

The composition is prepared according to the following procedure:

The SILMER and the KP 561 P and the oils of phase A are mixed under Rayneri at 70° C., until a clear mixture is obtained. It is then added to BENTO GEL and allowed to homogenize at 1500 revolutions/minute, for the necessary time.

The composition is a liquid and homogeneous lip product.

Example 5 Top Coat

An uncolored composition according to the invention is prepared.

The formula is shown in the table below. [Table 7]

SILMER® UR-1550 comprises Bis-hydroxypropyl dimethicone/SMDI copolymer at 45% by weight of dry matter in isododecane.

AMILON: Silica (and) Lauroyl lysine (95/5)

The composition is prepared according to the following protocol:

The composition is applied to the lips to form a film. It can be advantageously used as a Top Coat, after the application of a first layer of a colored film on the lips, to bring shine and shine hold.

Claims

33

1 . Homogeneous cosmetic composition for making up keratin materials, in particular the lips, comprising, in a physiologically acceptable medium, at least:

- one or more linear or branched C8-C19 alkane(s),

- one or more phenyl silicone oil(s), whose refractive index at 25°C is greater than 1.45, preferably greater than or equal to 1.47,

- a silicone-polyurethane polymer,

- And optionally additionally at least one pigment.

2. Composition according to claim 1, characterized in that it is a liquid and anhydrous composition.

3. Composition according to claim 1 or claim 2, characterized in that the silicone-polyurethane polymer is present in the composition in an active material content ranging from 14 to 25%, preferably from 16 to 20%, by weight per relative to the total weight of said composition.

4. Composition according to any one of claims 1 to 3, characterized in that it additionally comprises a lipophilic gelling agent, in particular a mineral gelling agent, preferably a bentone.

5. Composition according to any one of claims 1 to 4, characterized in that the branched C8-C19 alkanes are chosen from the group consisting of isododecane, isodecane, isohexadecane, hemi-squalane and mixtures thereof, preferably isododecane, and linear C8-C19 alkanes are chosen from the group consisting of n-dodecane, n-undecane, n-tridecane, n-tetradecane, n-pentadecane and their mixtures.

6. Composition according to any one of claims 1 to 5, characterized in that the silicone oil(s) comprising at least one phenyl group, the refractive index of which at 25° C. is greater than 1.45 , preferably greater than or equal to 1.47 are chosen from the group consisting of oils with INCI names phenylpropyldimethylsiloxysilicate, diphenyl dimethicone, diphenylsiloxyphenyltrimethicone, trimethyl pentaphenyl 34 trisiloxane, phenyltrimethicone, trimethylsiloxyphenyl dimethicone, and mixtures thereof.

7. Composition according to any one of claims 1 to 6, characterized in that it comprises at least one trimethyl pentaphenyl trisiloxane and optionally in addition a diphenylsiloxy phenyl trimethicone.

8. Composition according to any one of claims 1 to 6, characterized in that the silicone-polyurethane polymer is the reaction product of a polyorganopolysiloxane functionalized with hydroxyl groups, in particular having the structure of formula (I) [ Chem3] in which n is an integer between 0 and 5000, preferably between 1 and 200, more preferably between 10 and 100, and even more preferably between 10 and 50, with a diisocyanate compound, in particular chosen from the group consisting of diisocyanate 1,6-hexamethylene, dicyclohexyl methane-4,4'-diisocyanate, isophorone diisocyanate, and combinations thereof. Composition according to any one of Claims 1 to 8, characterized in that it also comprises a copolymer comprising carboxylate groups and polydimethylsiloxane groups. Composition according to any one of Claims 1 to 9, characterized in that it comprises: isododecane, preferably in a content ranging from 25 to 45% by weight relative to the total weight of the composition, a trimethyl pentaphenyl trisiloxane and optionally additionally a dipenylsiloxy phenyl trimethicone, preferably in respective contents ranging from 5 to 15% by weight and from 5 to 15% by weight relative to the total weight of the composition, and a silicone-polyurethane polymer reaction product a polyorganosiloxane functionalized with hydroxyl groups of formula Ib: [Chem3] where n is as defined above with a methylene diphenyl diisocyanate, in particular in a content of 16 to 25% by weight of dry matter relative to the total weight of the composition, - and advantageously in addition a copolymer comprising carboxylate groups and polydimethylsiloxane groups.

11 . Composition according to any one of the preceding claims, characterized in that it also comprises an ingredient chosen from a wax, a filler, a coloring matter and mixtures thereof. 12. Composition according to claim 11, characterized in that the fillers are chosen from the group consisting of silica powders, cellulose powders, cotton powders, and mixtures thereof.

13. Cosmetic process for caring for and/or making up keratin materials, in particular the lips, comprising the application, to said keratin materials, in particular the lips, of a composition according to any one of claims 1 to 12.