JP2019108275A - Composition for increasing accumulation of silicone to keratin fiber - Google Patents

Abstract

To provide a composition for increasing silicon accumulation to keratin fibers, more specifically, to hair.SOLUTION: There is provided a composition including (a) glutaric acid, (b) at least one kinds of aromatic alcohol, and (c) at least one kind of silicone, for treating keratin fibers, preferably, hair.SELECTED DRAWING: None

Description

  The present invention relates to a composition comprising glutaric acid, at least one aromatic alcohol and at least one silicone, for increasing silicone deposition on keratin fibres, in particular the hair.

  In the field of hair cosmetics, the hair conditioning effect is a very important property. It is well known that silicones impart a conditioning effect to hair. Heretofore, several prior art documents on rinse-off type hair care cosmetics containing silicone have been published.

  WO 2014/104340 is a component (A), a cationic polymer having a cationic charge density in the range of 4 meq / g to 10 meq / g (both ends included), a component (B), ie a fatty acid, a component (C), A rinse-off type hair cosmetic composition comprising a cationic surfactant, component (D), ie silicone, and component (E), ie either an organic or inorganic acid, wherein The mass ratio ((A) / (B)) of component A) to component (B) is in the range of 0.1 to 9 (including both end values), and component (A) and component (B) form a water-insoluble complex Discloses a hair cosmetic composition wherein the pH (at 25.degree. C.) of the composition when diluted 20 times is in the range of 2 to 5 (inclusive).

  However, there is still a need for hair care cosmetics with improved cosmetic effects such as smoothness, hair straightening efficiency and volume reduction efficiency. In particular, there is a need for hair care cosmetics that increase silicone deposition on keratin fibers, such as hair, to ensure the improved cosmetic effect resulting from silicone deposition on the surface of keratin fibers.

WO 2014/104340 EP0095238 U.S. Pat. No. 4,185,087 EP-A-0530974

Walter Noll, "Chemistry and Technology of Silicones" (1968), Academic Press CTFA Dictionary

  An object of the present invention is to provide a composition for increasing silicone deposition on keratin fibers, such as hair. In view of the increased silicone deposition on keratin fibers, the composition according to the invention is to achieve improved cosmetic effects, such as smoothness, hair straightening efficiency and volume down efficiency, on keratin fibers, eg hair. it can.

The above object of the present invention is
(a) Glutaric acid,
(b) at least one aromatic alcohol,
(c) It can be achieved by a composition for treating keratin fibers, preferably hair, comprising at least one silicone.

  The aromatic alcohol has the general formula (I):

(In the formula,
-a represents an integer of 0 to 5, preferably 0 to 2, more preferably 0 or 1,
-b represents an integer of 0 or 1;
-R represents H, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₆ alkenyl group,
-X represents a C ₁ -C ₄ alkylene or a C ₁ -C ₄ alkynylene group,
-Y represents a single bond, C ₁ -C ₄ alkylene or C ₁ -C ₄ alkynylene group)
Can be represented by

Preferably, in the general formula (I),
-a represents an integer of 0 or 1;
-b represents an integer of 0 or 1;
-R represents H, halogen or a C _{1 to} C ₆ alkyl group,
-X represents a C ₁ -C ₄ alkylene group,
-Y represents a single bond or a C ₁ -C ₄ alkylene group.

More preferably, in the general formula (I),
-a is 0,
-b is 1 and
-X represents a C ₁ -C ₄ alkylene group,
-Y represents a single bond.

  In a preferred embodiment of the invention, the aromatic alcohol is phenoxyethanol.

  Silicones include organopolysiloxanes such as polydialkylsiloxanes (PDMS), polydiarylsiloxanes and polyalkylarylsiloxanes, amino modified silicones, polyether modified silicones, carboxyl modified silicones, fatty acid modified silicones, alcohol modified silicones, fatty alcohol modified silicones And epoxy-modified silicones, fluorine-modified silicones, cyclic silicones, amino polyether-modified silicones, and mixtures thereof.

  The silicone can preferably be selected from organopolysiloxanes such as polydialkylsiloxanes (PDMS), polydiarylsiloxanes and polyalkylarylsiloxanes, amino-modified silicones, and mixtures thereof.

  Glutaric acid is present at a content ranging from 0.05% by mass to 20% by mass, preferably 0.1% by mass to 15% by mass, more preferably 0.5% by mass to 10% by mass, relative to the total mass of the composition be able to.

  The aromatic alcohol is present at a content ranging from 0.05% by mass to 10% by mass, preferably 0.1% by mass to 5% by mass, more preferably 0.2% by mass to 3% by mass, relative to the total mass of the composition can do.

  The silicone is present in a content ranging from 0.1% by mass to 30% by mass, preferably 0.5% by mass to 20% by mass, more preferably 1% by mass to 15% by mass, relative to the total mass of the composition. Can.

  The composition according to the present invention may further comprise at least one surfactant selected from cationic, anionic, nonionic and amphoteric surfactants.

  The composition according to the invention may further comprise at least one oil.

  In one embodiment of the invention, the composition according to the invention is a rinse-off cosmetic composition.

  The invention also relates to a cosmetic method for caring or conditioning keratin fibers, preferably the hair, comprising applying a composition according to the invention to the keratin fibers.

  As a result of intensive studies, the inventors have surprisingly found that the combination of glutaric acid, at least one aromatic alcohol and at least one silicone in a cosmetic composition for hair is keratin fibers such as hair. It has been found that improved amounts of silicone deposition can be provided on the surface, so that they complete the present invention.

Therefore, according to the present invention, a composition for treating keratin fibers, preferably hair,
(a) Glutaric acid,
(b) at least one aromatic alcohol,
(c) containing at least one silicone.

  By "keratin fiber" is meant herein a fiber comprising at least one keratinous substance. Preferably, at least a portion of the surface of the keratinous fiber is formed by keratinous material. Examples of keratin fibers include hair, eyebrows, eyebrows and the like. Preferably the invention is used to treat hair.

  In particular, the composition according to the invention has an excellent effect of increasing the amount of silicone deposition on keratin fibres, for example hair. Thus, the composition according to the invention can provide improved cosmetic effects such as smoothness, hair straightening efficiency and volume down efficiency that can result from silicone deposition on the surface of keratin fibers. Furthermore, the composition according to the invention can impart a lasting cosmetic effect to keratinous fibers, since the silicone deposition on keratinous fibers is increased.

The compositions according to the invention are described in detail hereinafter.
[Composition]
A composition for treating keratin fibers, preferably hair, according to the invention comprises (a) glutaric acid, (b) at least one aromatic alcohol and (c) at least one silicone.

(Glutaric acid)
The composition according to the invention comprises (a) glutaric acid.

  Glutaric acid has the following general formula:

Can be represented by

  The inventors have surprisingly found that the combination of glutaric acid and aromatic alcohol has a superior hair care and / or conditioning effect compared to any other combination where another dicarboxylic acid is used instead of glutaric acid. It has been found that it can provide excellent hair wave performance in hair permanent wave treatment as well as hair.

  (a) Glutaric acid is present at a content of 0.05% by mass or more, preferably 0.1% by mass or more, more preferably 0.2% by mass or more, still more preferably 0.5% by mass or more based on the total mass of the composition be able to. Glutaric acid can be present at a content of 20% by weight or less, preferably 15% by weight or less, more preferably 10% by weight or less, still more preferably 5% by weight or less, based on the total weight of the composition .

  (a) The content of glutaric acid is in the range of 0.05% by mass to 15% by mass, preferably 0.1% by mass to 10% by mass, more preferably 0.2% by mass to 5% by mass, based on the total mass of the composition Can exist. In another preferred embodiment, glutaric acid ranges from 0.05% to 20% by weight, preferably 0.1% to 15% by weight, more preferably 0.5% to 10% by weight, relative to the total weight of the composition. To be present in the content.

(Aromatic alcohol)
The composition according to the invention comprises (b) at least one aromatic alcohol. Two or more (b) aromatic alcohols may be used in combination. Thus, a single type of aromatic alcohol, or a combination of different types of aromatic alcohol can be used.

  As used herein, the term "aromatic alcohol" refers to at least one aromatic ring, and at least one alcohol function directly linked to the aromatic ring or linked to at least one substituent on the aromatic ring By any compound is meant a group, ie, an —OH group.

  (b) The aromatic alcohol may be a monoalcohol having one —OH group, or may be a polyol having two or more —OH groups, such as a dialcohol. Preferably, the aromatic alcohol is a monoalcohol.

  (b) The aromatic alcohol preferably comprises one or more benzene rings, naphthalene rings or furan rings. More preferably, the aromatic alcohol comprises one or more benzene rings. In particular, the aromatic alcohol can contain one benzene ring.

  In one preferred embodiment of the present invention (b) the aromatic alcohol comprises one benzene ring and one -OH group linked to a substituent on the benzene ring.

  (b) The aromatic alcohol can be a primary alcohol, a secondary alcohol or a tertiary alcohol. Preferentially, the aromatic alcohol is a primary alcohol.

  In a preferred embodiment of the present invention, the aromatic alcohol has the following general formula (I):

(In the formula,
-a represents an integer of 0 to 5, preferably 0 to 2, more preferably 0 or 1,
-b represents an integer of 0 or 1;
-R represents H, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₆ alkenyl group,
-X represents a C ₁ -C ₄ alkylene or a C ₁ -C ₄ alkynylene group,
-Y represents a single bond, C ₁ -C ₄ alkylene or C ₁ -C ₄ alkynylene group)
Can be indicated by

Each of said alkyl, alkoxy, alkenyl, alkylene and alkynylene groups may be linear or branched and is selected from halogen, amine group (—NH ₂ ) and oxo group (= O) May be substituted with one or more substituents.

  The halogen can be selected from F, Cl, Br and I, preferably the halogen is Cl.

According to a preferred embodiment of the present invention, in general formula (I):
-a represents an integer of 0 or 1;
-b represents an integer of 0 or 1;
-R represents H, halogen or a C _{1 to} C ₆ alkyl group,
-X represents a C ₁ -C ₄ alkylene group,
-Y represents a single bond or a C ₁ -C ₄ alkylene group.

According to a particularly preferred embodiment of the present invention, in general formula (I)
-a is 0,
-b is 1 and
-X represents a C ₁ -C ₄ alkylene group,
-Y represents a single bond.

  In another embodiment of the present invention, (b) the aromatic alcohol used herein is benzyl alcohol, benzyl glycol, phenoxyethanol, dichlorobenzyl alcohol, methylphenyl butanol, phenoxyisopropanol, 1-phenyl-1-propanol 1-phenyl-2-propanol, 2-phenyl-1-propanol, 2-phenyl-2-propanol, 3-phenyl-1-propanol, 1-phenylethyl alcohol, 2-phenylethyl alcohol, benzyloxyethanol, cinna It can be selected from milled alcohol, 4-methoxybenzyl alcohol, 4-methylbenzyl alcohol, and mixtures thereof. Particularly preferably, the aromatic alcohol is phenoxyethanol.

  (b) The aromatic alcohol can be present at a content of 0.05% by mass or more, preferably 0.1% by mass or more, more preferably 0.2% by mass or more, based on the total mass of the composition. The aromatic alcohol can be present at a content of 10% by weight or less, preferably 5% by weight or less, more preferably 3% by weight or less, based on the total weight of the composition.

  (b) aromatic alcohol is contained in a range of 0.05% by mass to 10% by mass, preferably 0.1% by mass to 5% by mass, more preferably 0.2% by mass to 3% by mass, with respect to the total mass of the composition It can be present in quantity.

(silicone)
The composition of the present invention comprises (c) at least one silicone. Two or more (c) silicones may be used in combination. As such, a single type of silicone or a combination of different types of silicones may be used.

In the context of the present invention, the term "silicone" as used herein is a linear or of variable molecular weight obtained by polymerization and / or condensation polymerization of appropriately functionalized silanes according to the generally accepted definition. It is understood to mean all organosilicon polymers or oligomers having a cyclic, branched or cross-linked structure, which are essentially essentially those whose silicon atoms are linked together via an oxygen atom The optionally substituted hydrocarbon-based group, consisting of a repeat of one of the units (≡Si-O-Si≡ siloxane bond), is bonded directly to the silicon atom via a carbon atom. The most common hydrocarbon groups are alkyl groups, in particular C ₁ -C ₁₀ alkyl groups, in particular methyl, fluoroalkyl and aryl groups, in particular phenyl groups.

  The silicone (c) used in the present invention can be volatile silicone, non-volatile silicone, or a combination thereof. Preferably (c) the silicone is a non-volatile silicone.

For simplicity, the dynamic viscosity of (c) silicone is referred to as "viscosity". The viscosity of (c) silicone at 25 ° C. is not particularly limited, but generally 5 mm ² / s to 30,000,000 mm ² / s, preferably 100 mm ² / s to 20,000,000 mm ² / s, more preferably 10,000 mm ² / s. It can be 1 second to 1,000,000 mm ² / second. The viscosity of the silicone (c) according to the invention is preferably measured using a Poiseuille rheometer at a temperature of 25 ° C. according to ASTM-D 445-97. When the silicone is used as a mixture in solvent or in the form of an emulsion, the viscosity of the silicone alone is independently measured as the viscosity of the mixed solvent.

  The mass average molecular weight (Mw) of the silicone (c) is not particularly limited, but in general, it can be in the range of 10000 to 400000, preferably 50000 to 300000, more preferably 10000 to 200000. The mass average molecular weight (Mw) of the silicone (c) according to the invention is measured at room temperature by gel permeation chromatography (GPC) as polystyrene equivalents. The column used is a microstila gel column. The eluent is THF and the flow rate is 1 ml / min. 200 μl of a solution containing 0.5% by weight silicone in THF are injected. Detection is performed by refractive index measurement and UV measurement.

  (c) Silicones include organopolysiloxanes such as polydialkylsiloxanes (PDMS), polydiarylsiloxanes and polyalkylarylsiloxanes, amino-modified silicones, polyether-modified silicones, carboxyl-modified silicones, fatty acid-modified silicones, alcohol-modified silicones, aliphatics It can be selected from alcohol-modified silicones, epoxy-modified silicones, fluorine-modified silicones, cyclic silicones, amino polyether-modified silicones, and mixtures thereof, but is not limited thereto. The silicone can preferably be selected from polydialkylsiloxanes, such as polydimethylsiloxanes and amino-modified silicones, in particular from amino-modified silicones.

  In a preferred embodiment, (c) the silicone comprises a combination of an organopolysiloxane and an amino-modified silicone.

  Organopolysiloxanes are more fully defined by Walter Noll, "Chemistry and Technology of Silicones" (1968), Academic Press. Among polydialkylsiloxanes, mention may be made, for example, of linear polydimethylsiloxanes having trimethylsilyl end groups and polydimethylsiloxanes having hydroxydimethylsilyl end groups. Among polydialkylaryl siloxanes, mention may be made, for example, of linear and branched polydimethylmethylphenylsiloxanes and polydimethyldiphenylsiloxanes.

  According to one embodiment (c) the silicone can be chosen from non-volatile polydialkylsiloxanes, for example from polydimethylsiloxanes having trimethylsilyl end groups, known under the trade name dimethicone.

  Non-limiting examples of commercial products corresponding to such polydialkylsiloxanes include BY22-029 (product of Toray Dow Corning Co., Ltd., nonionic emulsion of dimethicone oil), BY22-060 (Toray Dow Corning Co., Ltd.) Products, cationic emulsions containing a solution obtained by diluting highly polymerized dimethicone with low viscosity silicone), BY22-019 (product of Toray Dow Corning Co., Ltd., obtained by diluting highly polymerized dimethicone with cyclic silicone) (Nonionic and cationic emulsions containing the solution), BY22-020 (product of Toray Dow Corning Co., Ltd., cationic emulsion containing the solution obtained by diluting highly polymerized dimethicone with light liquid isoparaffin) , KM 902 (product of Shin-Etsu Chemical Co., Ltd., nonionic emulsion of highly polymerized dimethicone), KM 903 (Shin-Etsu Chemical Co., Ltd.) Co., Ltd. product, cationic emulsion containing a solution obtained by diluting highly polymerized dimethicone with low viscosity silicone), X-52-2127 (product of Shin-Etsu Chemical Co., Ltd., highly viscous dimethicone with low viscosity silicone) Cationic emulsion containing a solution obtained by dilution), X-52-2162 (product of Shin-Etsu Chemical Co., Ltd., non-ionic containing a solution obtained by diluting highly polymerized dimethicone with low viscosity silicone EMU 101 (Momentive Performance Materials, Inc. product, non-ionic emulsion containing solution obtained by diluting highly polymerized dimethicone with low viscosity silicone), XS 65-B 3803 (Momentive Performance Materials, Inc.) Product, nonionic emulsion containing a solution obtained by diluting highly polymerized dimethicone with low viscosity silicone), DC 7-3100 (Toray Dow Corning Silicon Co., Ltd.) Products manufactured by

  According to the invention, the term "amino-modified silicone" or aminosilicone comprises at least one primary, secondary or tertiary amine or one quaternary ammonium, more particularly at least one first Indicates any silicone, including a graded amine.

  The amino-modified silicone used in the present invention has the following formula (II):

[In the formula,
D is a hydrogen atom or phenyl, hydroxyl (-OH), or a C _{1 to} C ₈ alkyl group, preferably methyl or a C _{1 to} C ₈ alkoxy group, preferably a methoxy group,
i is an integer of 0, or an integer of 1 to 3, preferably 0;
k represents 0 or 1, and specifically 1;
j and l are numbers such that the sum (j + 1) may be in the range of 1 to 2000, particularly 50 to 150, and j indicates the number of 0 to 1999, specifically 49 to 149, And l can indicate 1 to 2000, and specifically 1 to 10,
R ₂ has the formula -C _q H _2q L {wherein, q is a number from 2 to 8, it is possible one or more hydrogen atoms are replaced by hydroxyl groups, L is
_{- N (R 3) -CH 2} -CH 2 -N (R '3) 2,
-N (R ₃ ) ₂ ,
_{^{- N + (R3) 3 Q}} -,
_{^{- N + (R 3) (}} H) 2 Q -,
^{_{- N + (R 3) 2}} HQ -,
_{- N (R 3) -CH 2} -CH 2 -N + (R '3) (H) 2 Q -
(Wherein R ₃ and R ′ ₃ can represent a hydrogen atom, phenyl, benzyl or a saturated monovalent hydrocarbon group such as a C _{1 to} C ₂₀ alkyl group, and Q and Q ⁻ can be, for example, , Anions such as fluoride ion, chloride ion, bromide ion or iodide ion)
An optionally quaternized amino group selected from the group of
Is a monovalent group]
You can choose from silicone.

  In particular, the amino-modified silicones corresponding to the definition of formula (II) have the following formula (III):

(Wherein R ₄ , R ₅ and R ₆ may be the same or different, and are a C _{1 to} C ₄ alkyl group, preferably CH ₃ ; a C _{1 to} C ₄ alkoxy group, preferably methoxy; or indicates OH; E is a linear or branched C ₃ -C _8, preferably represents C ₃ -C ₆ alkylene group; m and n are integers dependent on the molecular weight and the sum 1 Between 2000 and 2000)
It can be selected from compounds corresponding to

According to a first possible option, R ₄ , R ₅ and R ₆ may be identical or different and represent a C ₁ -C ₄ alkyl group, preferably a methyl or hydroxyl group, E Represents a C ₁ -C ₈ , preferably C ₃ -C ₄ alkylene group, and m and n are such that the mass average molecular weight of the compound is between about 5000 and 500,000. This type of compound is called "amodimethicone" in the CTFA dictionary.

According to a second possible option, R ₄ , R ₅ and R _{6, which} may be identical or different, represent a C ₁ -C ₄ alkoxy or hydroxyl group, and R ₄ or R ₅ of At least one is an alkoxy group, and E represents a C ₃ alkylene group. The molar ratio hydroxy / alkoxy is preferably between 0.2 / 1 and 0.4 / 1, preferably equal to 0.3 / 1. Furthermore, m and n are such that the mass average molecular weight of the compound is between 2000 and 1,000,000. More specifically, n is between 0 and 999, m is between 1 and 1000, and the sum of n and m is between 1 and 1000. Among the compounds of this category, mention may be made, inter alia, of the product Belsil® ADM 652 sold by the company Wacker.

According to a third possible option, R ₄ or R ₆ is different and represents a C ₁ -C ₄ alkoxy or hydroxyl group, at least one of the R ₅ or R ₆ groups is an alkoxy group, R ₅ represents a methyl group, and E represents a C ₃ alkylene group. The molar ratio hydroxy / alkoxy is preferably between 1 / 0.8 and 1 / 1.1, preferably equal to 1 / 0.95. Furthermore, m and n are such that the mass average molecular weight of the compound is between 2000 and 200,000. More specifically, n is between 0 and 999, m is between 1 and 1000, and the sum of n and m is between 1 and 1000. More particularly, mention may be made of the product Fluid WR® 1300 sold by the company Wacker and the product Xiameter® MEM-8299 Emulsion sold by the company Dow Corning.

  The amino-modified silicones used in the composition according to the invention preferably have the following general formula (IV):

[In the formula,
F represents a linear or branched alkylene group of C ₂ -C ₈ , preferably C ₂ -C ₆ , and even better C ₃ ;
R ₇ and R ₈ each independently represent a C _{1 to} C ₄ alkyl group, preferably a methyl group, or a C _{1 to} C ₄ alkoxy group, preferably a methoxy group or a hydroxy group, and m and n represent weight averages The number is such that the molecular weight (Mw) is 75,000 or more. Preferably, the R ₇ groups are identical and represent a hydroxyl group]
Have.

Preferably, the viscosity of the amino-modified silicone according to the invention is greater than 25,000 mm ² / s, measured at 25 ° C. More preferentially, the viscosity of the amino-modified silicone is between 30,000 and 200,000 mm ² / s at 25 ° C., and even more preferentially between 50,000 and 150,000 mm ² / s measured at 25 ° C. And still better still between 70,000 and 120,000 mm ² / s.

  Preferably, the cationic charge of the amino-modified silicone according to the invention is less than or equal to 0.5 meq / g, preferably in the range of 0.01 to 0.1 meq / g, still more preferably in the range of 0.03 to 0.06 meq / g. .

  Preferably, the amino-modified silicone according to the invention has a weight average molecular weight (Mw) ranging from 75,000 to 1,000,000, even more preferentially from 100,000 to 200,000.

  A particularly preferred aminosilicone corresponding to formula (IV) is, for example, Dow Corning 2-8299 Cationic Emulsion from Dow Corning.

  The product corresponding to the definition of formula (II) is, specifically, a polymer referred to in the CTFA dictionary as "trimethylsilyl amodimethicone" and has the following formula (V):

[Wherein n and m have the meanings given above according to formula (III)]
It corresponds to

  Such compounds are described, for example, in EP 0095 238 and compounds of the formula (V) are sold, for example, by the company OSI under the name Q2-8220.

Other aminosilicones according to the invention are quaternized aminosilicones, which are specifically:
(a) the following formula (VI):

[In the formula,
R ₈ represents a C _{1 to} C ₁₈ alkyl group such as methyl,
R ₉ represents a divalent hydrocarbon group, specifically a C _{1 to} C ₁₈ alkylene group,
Q ^- is an anion, specifically a chloride ion,
o represents an average statistic of 2 to 20, specifically 2 to 8,
p represents an average statistic of 20 to 200, specifically 20 to 50]
Compound equivalent to Such compounds are described in more detail in US Pat. No. 4,185,087. The compounds falling into this class are the products sold by Union Carbide under the name Ucar Silicone ALE 56.
(b) Formula (VII):

[In the formula,
R _{10, which} may be identical or different, represents a monovalent hydrocarbon radical containing 1 to 8 carbon atoms, in particular a C _{1 to} C ₈ alkyl group such as methyl,
R ₁₂ is a divalent hydrocarbon group, in particular a C _{1 to} C ₁₈ alkylene group, or a divalent C _{1 to} C ₁₈ , for example a C _{1 to} C ₈ alkyleneoxy group, which is linked to Si via a SiC bond Represents
R _{11, which} may be the same or different, is a hydrogen atom, a monovalent hydrocarbon group containing 1 to 18 carbon atoms, specifically a C _{1 to} C ₁₈ alkyl group, C _{2 to} C ₁₈ alkenyl group or -R ₁₂ -NHCOR ₁₀ group is represented
X ^- is an anion such as a halide ion, in particular a chloride ion, or an organic acid salt (such as acetate),
r represents an average statistic of 2 to 200, specifically 5 to 100)
Quaternary ammonium silicone. These silicones are described, for example, in the application EP-A-0530974.
(c) Formula (VIII):

(In the formula,
-R ₁₃ , R ₁₄ , R ₁₅ and R _{16, which} may be the same or different, each represents a C _{1 to} C ₄ alkyl group or a phenyl group,
-R ₁₇ represents a C _{1 to} C ₄ alkyl group or a hydroxyl group,
-r is an integer ranging from 1 to 5,
-s is an integer ranging from 1 to 5,
Where t is selected such that the amine number is between 0.01 and 1 meq / g)
Amino-modified silicone.

  Preferably, the amino-modified silicones according to the invention are non-quaternized, ie they do not contain a nitrogen atom which has a permanent charge.

  Preferably, the amino-modified silicone of the present invention is amodimethicone, such as amodimethicone sold by the supplier Shin-Etsu Chemical Co., Ltd. under the name KF 8020 or by the supplier MOMENTIVE PERFORMANCE MATERIALS, under the trade name SILSOFT 253. . Another preferred amino-modified silicone is amodimethicone of formula (F) sold by Dow Corning under the trade name XIAMETER® MEM-8299 Caticic Emulsion. Another preferred amino-modified silicone is amodimethicone sold by Dow Corning under the trade name Dow Corning® 969 EMULSION.

  Another preferred amino-modified silicone which may be used in the composition of the invention is aminopropyl dimethicone, such as aminopropyl dimethicone sold by Shin-Etsu Chemical Co., Ltd. under the name KF-8015.

  In another embodiment, the amino-modified silicone according to the invention is selected from bis-cetearyl amodimethicone (sold by the company Momentive under the name SILSOFT AX).

  Another preferred aminosilicone that may be used in the composition of the present invention is aminopropyl dimethicone, such as aminopropyl dimethicone sold by Shin-Etsu Chemical Co., Ltd. under the name KF-8015.

  Particularly preferred (c) silicones according to the invention are polysiloxanes containing amino groups, such as aminodimethicone or trimethylsilylaminodimethicone, in particular compounds of the formulas (III), (IV) and (V).

  The silicone (c) used in the present invention can also be a silicone gum. The term "silicone gum" as used herein is used alone or as a volatile silicone, polydimethylsiloxane (PDMS) oil, polyphenylmethylsiloxane (PPMS) oil, isoparaffin, methylene chloride, pentane or these A polyorganosiloxane having a weight average molecular weight (Mw) of 200,000 to 2,000,000, which is used as a mixture in a solvent selected from a mixture of and which can have, for example, one of the following structures: : Polydimethylsiloxane, poly [(dimethylsiloxane) / (methylvinylsiloxane)], poly [(dimethylsiloxane) / (vinylhydrogenosiloxane)], poly [(dihydrogenodimethylsiloxane) / (divinylsiloxane)], poly [(Dimethylsiloxane) / (diphenylsiloxane)], poly [(dimethylsiloxane) / (phenylmethyl)] Loxane)], and poly [(dimethylsiloxane) / (diphenylsiloxane) / (methylvinylsiloxane)].

  (c) The silicone can be used as it is or in the form of a solution in an organic solvent or else in the form of an emulsion or microemulsion. Preferably, the silicone is in the form of an aqueous emulsion. The term "aqueous emulsion" is intended to mean an oil-in-water type emulsion in which the silicone copolymer is dispersed in the form of particles or droplets in the aqueous phase forming the continuous phase of the emulsion. The silicone emulsion can have a silicone droplet size or particle size ranging from 10 nm to 50 μm, preferably 0.3 nm to 20 μm. Particle size is measured by laser granulometry. This emulsion can be stabilized in conventional emulsion systems. The emulsifying system comprises a surfactant commonly used in silicone emulsions. These surfactants can be nonionic, cationic, anionic or amphoteric surfactants, or mixtures thereof.

  The silicone (c) may be present at a content of at least 0.1% by weight, preferably at least 1% by weight, more preferably at least 2% by weight, based on the total weight of the composition. The aromatic alcohol can be present at a content of 30% by weight or less, preferably 20% by weight or less, more preferably 15% by weight or less, based on the total weight of the composition.

  (c) silicone is used in a content in the range of 0.1% by mass to 30% by mass, preferably 0.5% by mass to 20% by mass, more preferably 1% by mass to 15% by mass with respect to the total mass of the composition It can exist.

  In a preferred embodiment (c) the silicone comprises organopolysiloxanes such as polydialkylsiloxanes (PDMS), polydiarylsiloxanes and polyalkylarylsiloxanes in an amount of 0.1% to 30% by weight relative to the total weight of the composition. Preferably, the content is in the range of 0.5% by mass to 20% by mass, more preferably 1% by mass to 15% by mass.

  In a preferred embodiment, (c) silicone is amino-modified silicone in an amount of 0.1% by mass to 30% by mass, preferably 0.5% by mass to 20% by mass, more preferably 1% by mass, based on the total mass of the composition The content may be in the range of -15% by mass.

(Other ingredients)
Surfactants The compositions according to the invention can preferably comprise at least one surfactant. Surfactants used in the present invention include cationic, anionic, nonionic and amphoteric surfactants.

Nonionic surfactants may include the following:
-Polyethoxylated fatty alcohols or polyglycerolated fatty alcohols, such as ethylene oxide adducts of lauryl alcohol, in particular those containing 9 to 50 oxyethylene units (in the CTFA name laureth-9 to laureth-50); ethylene oxide of behenyl alcohol Adducts, in particular those containing 9 to 50 oxyethylene units (CTFA names Beheness-9 to Behenes-50); ethylene oxide adducts of cetyl alcohol, in particular those containing 10 to 30 oxyethylene units ( CTEF names ceteth-10 to ceteth-30); ethylene oxide adducts of stearyl alcohol, especially those containing 2 to 20 oxyethylene units (CTFA names steareth-2 to steareth-20); ethylene oxide addition of oleyl alcohol , Especially those containing 10 to 30 oxyethylene units (in the CTFA name I Sus -10 to Ores -30, eg Ores -20);
-Esters of sugars with C ₈ -C ₂₄ fatty acids and their oxyalkylenated derivatives, such as polyethoxylated sorbitol esters of C ₈ -C ₂₄ fatty acids, in particular the products sold by Croda under the name “TWEEN 80” Polysorbate 80; Ether of sugar and C ₈ -C ₂₄ fatty alcohol, eg Caprilyl / Capryl glucoside, such as the product sold under the name “ORAMIX CG 110” by the company SEPPIC
Esters of fatty acids, in particular C ₈ -C ₂₄ , preferably C ₁₆ -C ₂₂ fatty acids, with polyols, in particular glycerol or sorbitol, eg glyceryl stearate sold under the name Tegin M® by the company Goldschmidt Polyglyceryl diisostearate, polyglyceryl isostearate, polyglyceryl monostearate, diglyceryl tetraisostearate, polyethylene glycol diisostearate, polyglyceryl pentastearate-10, glyceryl monooleate, glyceryl laurate, eg product Imwitor 312® by Hills ), (Di) diethylene glycol dilaurate, decaglyceryl pentaoleate, decaglyceryl pentadiisostearate, glyceryl caprylic / caprylic acid, polyglyceryl (iso) stearate and (Poly) ricinoleic acid polyglyceryl-2,
-An oxyalkylenated alcohol, in particular an oxyethylenated and / or oxypropyleneified alcohol which may contain 1 to 15 oxyethylene units and / or oxypropylene units, in particular an ethoxylated C ₈ -C ₂₄ , preferably C ₁₂ -C ₁₈ fatty alcohols, for example stearyl alcohol (CTFA name: Steareth-2, eg Brij 72 sold by Uniqema) which is ethoxylated with two oxyethylene units, or oxyethylenated oleyl alcohol.

Anionic surfactants may include the following:
Salts of C ₁₆ -C ₃₀ fatty acids, in particular amine salts, such as triethanolamine stearate or 2-amino-2-methylpropane-1,3-diol stearate
-Polyoxyethylenated fatty acid salts, in particular aminated salts or salts of alkali metals, and mixtures thereof
-Phosphoric esters and their salts, such as DEA oleth-10 phosphate (Crodafos NION from Croda), or monopotassium monocetyl phosphate (Amphisol K from Givaudan, or Arlatone MAP 160K from Uniqema),
-Sulfosuccinates, for example PEG-5 lauryl citric acid disodium sulfosuccinate and licinoleamide MEA sulfosuccinate disodium,
-Sulfuric acid alkyl ethers such as sodium lauryl ether sulfate,
-Isethionate,
-Acyl glutamates, such as hydrogenated tallow glutamate disodium (Amisoft HS-21 R® sold by Ajinomoto Co., Ltd.), and mixtures thereof.

As cationic surfactants there may be mentioned:
-Alkylimidazolidiniums, such as isostearylethylimidinium ethosulphate,
- ammonium salts such as (C ₁₂ -C ₃₀ alkyl) tri (C ₁ ~ ₄ alkyl) ammonium halides, N is the way of example, N, N-trimethyl-1-docosanoic aminium chloride or Behentorimoniumukurorido.

  Amphoteric surfactants can include N-acyl amino acids such as N-alkyl aminoacetates and disodium cocoamphodiacetate, and amine oxides such as stearamine oxide and lauramine oxide.

  The surfactant is present in a content ranging from 0.01% by mass to 30% by mass, preferably from 0.1% by mass to 20% by mass, more preferably from 1% by mass to 15% by mass, based on the total mass of the composition. can do.

-Oils The composition according to the invention may preferably comprise at least one oil. The oil can be volatile or non-volatile. Preferably, the oil can be a non-volatile oil.

Nonvolatile hydrocarbon-based oils can be selected from:
-Animal-derived hydrocarbon oils such as perhydrosqualene,
-Hydrocarbon-based oils of vegetable origin, such as phytostearyl esters such as phytostearyl oleate, phytostearyl isostearate and lauroyl / octyldodecyl / phytostearyl glutamate, triglycerides formed from fatty acid esters of glycerol, in particular fatty acids thereof May have a chain length in the range of C ₄ -C ₃₆ , in particular C ₁₈ -C ₃₆ , these oils are optionally linear or branched, saturated or unsaturated; These oils are, in particular, heptanoic acid or octanoic acid triglycerides, shea oil, alfalfa oil, poppy seed oil, winter pumpkin oil, millet oil, barley oil, quinoa oil, rye oil, kuoi oil, cassava oil, passionflower oil, shea butter, aloe vera oil Sweet almond oil, peach kernel oil, peanut oil, argan oil, avocado oil, baobab , Borage oil, broccoli oil, calendula oil, camelina oil, canola oil, canola oil, carrot oil, safflower oil, linseed oil, rapeseed oil, rapeseed oil, cotton seed oil, coconut oil, pepo pumpkin seed oil, wheat germ oil, jojoba oil, lily oil, macadamia Oil, Corn Oil, Meadow Foam Oil, Monoy Oil, Hazelnut Oil, Apricot Kernel Oil, Walnut Oil, Olive Oil, Evening Primrose Oil, Palm Oil, Black Currant Seed Oil, Kiwi Seed Oil, Grape Seed Oil, Pistachio Oil, Winter Pumpkin Oil, Pumpkin Oil, quinoa oil, muscose oil, sesame oil, soybean oil, sunflower oil, castor oil and watermelon oil, and mixtures thereof, or caprylic / capric triglycerides,
-Linear or branched hydrocarbons of mineral or synthetic origin, such as liquid paraffin and its derivatives, petrolatum, mineral oil, polydecenes, polybutenes, hydrogenated polyisobutenes, such as Parleam, and squalane,
Synthetic ethers containing 10 to 40 carbon atoms,
Synthetic esters, for example of the formula R ₁ COOR _{2 where} R ₁ represents a linear or branched fatty acid residue containing 1 to 40 carbon atoms, R ₂ is 1 to 40 Oils containing in particular carbon atoms containing, in particular, branched hydrocarbon chains, provided that R ₁ + R ₂ R10). The esters are in particular fatty acid esters of alcohols, such as cetyl esters, in particular cetostearyl octanoate, isopropyl alcohol esters, such as isopropyl myristate, isopropyl palmitate, ethyl palmitate, 2-ethylhexyl palmitate, isopropyl stearate, isostearin Isopropyl stearate, isostearyl isostearate, octyl stearate, hydroxylated esters such as isostearyl lactate, octyl hydroxystearate, diisopropyl adipate, heptanoic acid esters, in particular heptanoic acid isostearyl, octanoic acid alcohol or polyalcohol, decane Acid ester or ricinoleate ester such as propylene glycol dioctanoate, cetyl octanoate, octo Phosphate tridecyl, 2-ethylhexyl 4-Jiheputanoeto, 2-ethylhexyl palmitate, alkyl benzoate, polyethylene glycol diheptanoate, propylene glycol 2-diethyl hexanoate, and mixtures thereof, benzoic acid C ₁₂ -C ₁₅ alcohol, lauric Hexyl acid, neopentanoate such as isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate, octyldodecyl neopentanoate, isononanoic acid ester such as isononyl isononanoate, isotridecyl isononanoate, octyl isononanoate, hydroxylated ester Examples may be selected from isostearyl lactate and diisostearyl malate,
Fluoro oils, which are optionally partially hydrocarbon based and / or silicone based, such as fluorosilicone oils, fluoropolyethers and fluorosilicones,
-Saturated or unsaturated, linear or branched, fatty alcohols containing 6 to 30 carbon atoms, more particularly 8 to 30 carbon atoms: cetyl alcohol, which may be mentioned Stearyl alcohol and mixtures thereof (cetyl stearyl alcohol), octodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleyl alcohol, and
-A mixture of these.

  The oil is present in a content ranging from 0.1% by mass to 30% by mass, preferably 0.5% by mass to 20% by mass, more preferably 1% by mass to 15% by mass, relative to the total mass of the composition Can.

Aqueous Medium The composition according to the invention can preferably comprise an aqueous medium. The aqueous medium is made of water; or water and a C ₁ -C ₄ lower alcohol such as ethanol, isopropanol, tert-butanol or n-butanol; a polyol such as glycerin, propylene glycol and polyethylene glycol; and mixtures thereof It is preferably made of a mixture with at least one cosmetically acceptable solvent of choice.

  The aqueous medium is present at a content ranging from 20% by weight to 99% by weight, preferably from 30% by weight to 95% by weight, more preferably from 40% by weight to 90% by weight, based on the total weight of the composition. be able to.

pH adjusters The compositions according to the invention can preferably comprise at least one pH adjuster. Adjustment of the pH to the desired value can be carried out conventionally by adding a pH adjuster, such as an organic or inorganic base, or an organic or inorganic acid, or a salt thereof to the composition. Bases are, for example, ammonium hydroxide, sodium hydroxide, sodium carbonate or primary, secondary or tertiary (poly) amines, such as monoethanolamine, diethanolamine, triethanolamine, isopropanolamine or 1,3 -Propanediamine is mentioned. Organic acids include, for example, carboxylic acids, citric acid and lactic acid. Inorganic acids include, for example, hydrochloric acid, nitric acid, orthophosphoric acid and sulfonic acid. Salts include, for example, sodium phosphate and trisodium phosphate.

  The pH adjuster has a content sufficient to adjust the pH of the composition to a desired value, for example, 0.01% by mass to 10% by mass, preferably 0.1% by mass to 5% by mass with respect to the total mass of the composition. %, More preferably in a content ranging from 0.5% by weight to 3% by weight.

-Additives The compositions according to the invention are all customary adjuvants encountered in the field of compositions for treating keratin fibers, such as hydrophilic solvents, fragrances, fragrances, thickeners, chlorhexidine digluconate etc. It may further contain preservatives, sequestering agents such as EDTA (ethylenediaminetetraacetic acid) and salts thereof, foam control agents, coloring agents, moisturizers, antidandruff agents, antiseborrhoeants, sunscreens and the like.

  The amount of additives contained in the composition according to the invention is not limited, but can be from 0.01 to 30% by weight, based on the total weight of the composition according to the invention.

  The composition according to the invention can be present in any form such as a lotion, a gel, a thickened or non-thickened W / O or O / W emulsion, a foam or a cream. The composition according to the invention can be contained in any container, such as a spray bottle, a pump bottle or an aerosol can.

  The composition according to the invention can be used as a composition for treating keratin fibres. For example, the composition may be a shampoo, conditioner, hair treatment cream, gel, mousse, pump hair spray, aerosol hair spray, set lotion, blow styling lotion, hair color lotion, hair straightening composition, permanent wave It can be incorporated into reducing agents, permanent wave neutralizing agents, and coloring compositions.

  In particular, the composition according to the present invention has an excellent hair straightening effect, a hair volume down effect and a smoothness imparting effect on the hair in view of the increase in the silicone deposition amount on the surface of the hair. Is suitable for hair care treatment compositions. Preferably, the composition according to the invention can be a rinse-off (washing out) type hair care treatment composition.

  The pH of the composition according to the invention can generally be, for example, 2-12. When the composition is used as a hair care treatment composition, the composition can have a pH ranging from 3.0 to 6.0, preferably 3.5 to 5.0.

  The composition according to the invention can be prepared, for example, by mixing (a) glutaric acid and (b) aromatic alcohol and (c) silicone through the usual techniques in the art. The other ingredients mentioned above can be mixed with glutaric acid, aromatic alcohol and (c) silicone. While mixing these components, they can be heated if necessary.

[Beauty method]
The present invention is also a method, preferably a cosmetic method of treating keratinous fibers, preferably a method of conditioning or care of the hair, comprising applying a composition according to the present invention to keratinous fibers, preferably hair. It also relates to the method.

  The composition can be applied to the hair by first applying it to the hand and then contacting the hair with the hand, and in other embodiments the composition is applied directly to the hair, such as by spraying. It can be applied. The composition may also be delivered to the hair by use of an applicator or device such as a brush. The composition may be applied to the hair as a leave on or rinse off treatment.

  In one embodiment of the present invention, this composition can be used as a hair care composition or a hair conditioning composition. Thus, the present invention also relates to the use of a combination of glutaric acid, an aromatic alcohol and a silicone as a hair care composition or a hair conditioning composition.

  In view of the excellent hair frizzing correction effect, the hair volume reducing effect and the smoothness imparting effect of the composition according to the present invention, the cosmetic method according to the present invention can impart an attractive appearance to the hair it can. Furthermore, since the amount of silicone deposition on keratinous fibers is increased, the cosmetic method according to the invention can impart a permanence to cosmetic effects on keratinous fibers.

  The invention is explained in more detail by means of examples. However, these examples should not be construed as limiting the scope of the present invention.

  In the examples, glutaric acid used is obtained from Tokyo Chemical Industry Co., Ltd. (reagent grade), phenoxyethanol used is obtained from SEPPIC, and amino-modified silicone used is named DOW CORNING® 969 EMULION from DOW CORNING. The polydimethylsiloxane used was obtained from Shin-Etsu Chemical Co., Ltd. under the name "X-52-2127". Shin-Etsu Chemical's X-52-2127 contains 75% polydimethylsiloxane, and Dow Corning 969 Emulsion contains 30% amodimethicone.

(Examples 1 and 2 and Comparative Examples 1 to 6)
[Composition]
The compositions according to Examples 1 and 2 and Comparative Examples 1 to 6 were prepared according to the following preparation protocol. The composition is shown in Table 1 below. In Table 1 (table 1), all ingredients are based on "mass%" of the active ingredient.

Preparation Protocol
1) Glycerin, cetyl ester, mineral oil, stearyl alcohol and glutaric acid (if present) were added to deionized water at 80 ° C. in a beaker and they were mixed.
2) Behentrimonium chloride was added to obtain an emulsified mixture, and then the mixture was cooled to about 45 ° C.
3) Polydimethylsiloxane and amodimethicone (if present) were added to this mixture.
4) Phenoxyethanol (if present), chlorhexidine digluconate and fragrance were added to this mixture.
5) The pH of the resulting mixture was adjusted to 4.0 with sodium hydroxide.
6) The total amount was adjusted with deionized water. The resulting mixture was mixed to be homogeneous.

[Evaluation]
(Measurement of silicone deposition)
Three hair swatches (1 g, 27 cm) were prepared for each experiment. Each of the swatches was washed with clear shampoo and then placed on a hot plate at 30 ° C. 0.4 g of each of the compositions according to Examples 1 and 2 and Comparative Examples 1 to 6 were brushed on each swatch. The swatches were then wrapped, kept at 30 ° C. and ambient humidity for 5 minutes, rinsed off under running water, and then allowed to dry naturally under ambient conditions to obtain a treated swatch. The processed swatches were cut into short pieces for measurement. The amount of silicone deposited on the sample was analyzed by X-ray fluorescence analysis (XRF) using a wavelength dispersive X-ray fluorescence spectrometer (manufacturer: Thermo Fisher Scientific KK, Model: WDXRF ARL Optim'x Thermofisher 2104 (Wavelength Dispersion) It measured using XRF system). The mean value was calculated with 3 hair swatches for each composition.

  The results are shown in Table 1 (Table 1).

  As seen from the results of the measurement of the amount of silicone deposition on the hair swatch in Table 1 (Table 1), the composition according to Example 1 comprising the combination of glutaric acid, aromatic alcohol and silicone Or, more silicone deposits on the hair swatch were applied as compared to the compositions according to Comparative Examples 1 to 3 containing no aromatic alcohol. Similarly, the composition according to Example 2 comprising the combination of glutaric acid, aromatic alcohol and silicone is more in comparison with the composition according to comparative examples 4 to 6 not containing glutaric acid and / or aromatic alcohol. , Silicone deposit on the hair swatch. It is noted that the composition according to Example 2 comprising an amino-modified silicone as silicone gave a very high amount of silicone deposition on the hair swatch.

(Example 3 and Comparative Examples 7 to 13)
[Composition]
The compositions according to Example 3 and Comparative Examples 7-13 were prepared according to the following preparation protocol. The composition is shown in Table 2 below. In Table 2 all ingredients are based on "% by weight" of the active ingredient. The amount of each of the dicarboxylic acids was set to 0.015 mol.

Preparation Protocol
1) Glycerin, cetyl ester, mineral oil, stearyl alcohol and different dicarboxylic acids (if present) were added to deionized water at 80 ° C. in a beaker and they were mixed.
2) Behentrimonium chloride was added to obtain an emulsified mixture, and then the mixture was cooled to about 45 ° C.
3) Polydimethylsiloxane and amodimethicone were added to this mixture.
4) Phenoxyethanol (if present), chlorhexidine digluconate and fragrance were added to this mixture.
5) The pH of the resulting mixture was adjusted to 4.0 with sodium hydroxide.
6) The total amount was adjusted with deionized water. The resulting mixture was mixed to be homogeneous.

[Evaluation]
(Hair straightening efficiency and volume down efficiency)
Three hair swatches (1 g, 27 cm) were prepared for each experiment. The swatches were washed with clarifying shampoo and then placed on a hot plate at 30 ° C. 0.4 g of each of the compositions according to Example 3 and Comparative Examples 7 to 13 were brushed onto the swatches. The swatches were then wrapped, molded for 5 minutes at 30 ° C. and ambient humidity, rinsed off under running water, and then allowed to dry naturally under ambient conditions to obtain a treated swatch.

The length and width of the hair swatches before and after treatment were measured by caliper. The length was measured from the root to the tip of the hair swatch and the width was measured by placing the caliper at a position 20 cm from the root of the hair swatch perpendicular to the axis of the vertically suspended hair swatch. Hair straightening efficiency and volume down efficiency were each determined according to the following equation: The mean value was calculated with 3 hair swatches for each composition.
Hair straightening efficiency = (L _after- L _before ) / L _before × 100%
_Before L: Length of hair swatch before treatment
_After L: Length of hair swatch after treatment The higher the value (%) of the hair removal efficiency, the more the composition has the better hair removal efficiency.
Volume down efficiency = (W _after- W _before ) / W _before × 100%
_Before W: Width of hair swatch before treatment
_After W: Width of hair swatch after treatment The smaller the value (%) of the volume down efficiency, it means that the composition has an excellent volume down efficiency.

(Smoothness)
Three hair swatches (1 g, 27 cm) were prepared for each experiment. The swatches were washed with clarifying shampoo and then placed on a hot plate at 30 ° C. 0.4 g of each of the compositions according to Example 3 and Comparative Examples 7 to 13 were brushed onto the swatches. The swatches were then wrapped, kept at 30 ° C. and ambient humidity for 5 minutes, rinsed off under running water, and then allowed to dry naturally under ambient conditions to obtain a treated swatch. The treated swatch was placed on a plate and its root side was fixed on the plate with a hair clip. The smoothness of the treated hair swatches was measured by scanning the hair swatch root to tip using a sensor (Handy Rub Tester (type TL 701) from Trinity Lab). This measurement was performed three times per treated hair swatch. The same procedure was followed for two more hair swatches to obtain a total of nine results per composition, and an average value was calculated for each composition. The smaller the score, the better the smoothness effect exhibited.

  The results are shown in Table 2 (Table 2).

  Example 3 including a combination of glutaric acid, aromatic alcohol and silicone, as seen from the results of the evaluation in hair cosmetic effects of hair straightening efficiency, volume down efficiency and smoothness in Table 2 (Table 2) The compositions according to Example 4 exhibited the best performance among the compositions tested at all cosmetic properties evaluated.

(Example 4)
The permanence of the silicone deposit was evaluated using a hair swatch treated with the composition according to Example 3 above as a sample. The hair swatches were washed a given number of times with a shampoo composition. The cleaned swatches were cut into short pieces for measurement. The amount of silicone deposited on the swatch after shampooing was measured by X-ray fluorescence spectrometry (XRF) using a wavelength dispersive X-ray fluorescence spectrometer (manufacturer: Thermo Fisher Scientific KK, Model: WDXRF ARL Optim'x Thermofisher 2104 (Wavelength Measurements were made using the Dispersion) XRF system). The composition of the shampoo composition is shown in Table 3 below. In Table 3 (Table 3), all ingredients are based on "mass%" of the active ingredient.

  The results are shown in Table 4 (Table 4).

  As can be seen from the results of the measurement of the amount of silicone deposition on the hair swatch, the hair swatches treated with the composition according to the invention have their initial silicone deposition level even after shampooing them 3 and 10 times respectively It maintained about 1/3 times and about 1/20 times. Thus, it can be said that the composition according to the invention can impart improved persistence of cosmetic effects to keratin fibers, such as hair, resulting from silicone deposition.

  Thus, the composition according to the present invention provides silicone deposition on keratin fibers, such as the hair, in order to achieve improved cosmetic effects such as hair straightening efficiency, volume reduction efficiency and smoothness and permanence of the cosmetic effect. It can be concluded that it may be very preferable to use to increase

Claims (14)

(a) Glutaric acid,
(b) at least one aromatic alcohol,
(c) A composition for treating keratin fibers, preferably hair, comprising at least one silicone. The aromatic alcohol has the general formula (I):

(In the formula,
-a represents an integer of 0 to 5, preferably 0 to 2, more preferably 0 or 1,
-b represents an integer of 0 or 1;
-R represents H, halogen, a C _{1 to} C ₆ alkyl group, a C _{1 to} C ₆ alkoxy group or a C _{1 to} C ₆ alkenyl group,
-X represents a C ₁ -C ₄ alkylene group or a C ₁ -C ₄ alkynylene group,
-Y represents a single bond, a C _{1 to} C ₄ alkylene group or a C _{1 to} C ₄ alkynylene group)
The composition according to claim 1, which is represented by In the general formula (I),
-a represents an integer of 0 or 1,
-b represents an integer of 0 or 1;
-R represents H, halogen or a C ₁ -C ₆ alkyl group,
-X represents a C ₁ -C ₄ alkylene group,
-Y represents a single bond or a C _{1 to} C ₄ alkylene group,
A composition according to claim 2. In the general formula (I),
-a is 0,
-b is 1,
-X represents a C ₁ -C ₄ alkylene group,
-Y represents a single bond,
A composition according to claim 3.   The composition according to claim 1, wherein the aromatic alcohol is phenoxyethanol.   Silicones include organopolysiloxanes such as polydialkylsiloxanes (PDMS), polydiarylsiloxanes and polyalkylarylsiloxanes, amino-modified silicones, polyether-modified silicones, carboxyl-modified silicones, fatty acid-modified silicones, alcohol-modified silicones, fatty alcohol-modified silicones The composition according to any one of claims 1 to 5, selected from epoxy-modified silicones, fluorine-modified silicones, cyclic silicones, amino polyether-modified silicones, and mixtures thereof.   A silicone according to any one of the preceding claims, wherein the silicone is selected from organopolysiloxanes such as polydialkylsiloxanes (PDMS), polydiarylsiloxanes and polyalkylarylsiloxanes, amino-modified silicones, and mixtures thereof. Composition.   Glutaric acid is present at a content ranging from 0.05% to 20% by weight, preferably 0.1% to 15% by weight, more preferably 0.5% to 10% by weight relative to the total weight of the composition The composition according to any one of claims 1 to 7.   The aromatic alcohol is present in a content ranging from 0.05% by mass to 10% by mass, preferably 0.1% by mass to 5% by mass, more preferably 0.2% by mass to 3% by mass, relative to the total mass of the composition A composition according to any one of the preceding claims.   The silicone is present in a content ranging from 0.1% to 30%, preferably from 0.5% to 20%, more preferably from 1% to 15% by weight relative to the total weight of the composition. A composition according to any one of the preceding claims.   The composition according to any one of claims 1 to 10, further comprising at least one surfactant selected from cationic, anionic, nonionic and amphoteric surfactants.   12. A composition according to any one of the preceding claims, further comprising at least one oil.   The composition according to any one of the preceding claims, which is a rinse-off cosmetic composition.   A cosmetic method for caring or conditioning keratin fibers, preferably hair, comprising the step of applying the composition according to any one of claims 1 to 13 to keratin fibers.