FR3075044A1 - HAIR TREATMENT PROCESS USING FLAVIN DERIVATIVE, PROTEIN AND LUMINOUS RADIATION - Google Patents

Abstract

 The present invention relates to a method for treating hair, comprising the application of a composition comprising i) at least one flavin derivative and ii) at least one polyamino acid, and at least one step of exposing said materials to light radiation. artificial or natural, in particular for the care and / or repair of hair.

Description

METHOD FOR TREATING HAIR USING FLAVIN DERIVATIVE, PROTEIN AND LIGHT RADIATION

The present invention relates to a method for treating hair, comprising the application of a composition comprising i) at least one flavin derivative and ii) at least one polyamino acid, and at least one step of exposing said materials to light radiation. artificial or natural, in particular for the care and / or repair of hair.

Outdoor atmospheric agents such as pollution and bad weather, as well as mechanical or chemical treatments such as brushing, combing, dyes, discoloration, perms, straightening, repeated washing, damage and weaken the hair. The hair is thus damaged and can in the long term become dry, coarse, brittle, dull, split ends and / or soft or even sensitive to humidity by making the hair unruly, often with frizz, and / or difficult to comb in the middle. wet, especially in very humid environments. The hair is then also sensitive to mechanical stresses such as tightening by an elastic means to make for example a ponytail, and keep the trace of the tightening even after having removed the elastic bracelet. When the hair is soft, it is difficult to style and give it volume, especially near the scalp. We often speak by abuse of language of "flat hair" to express this lack of volume near the root.

To remedy these drawbacks, it is customary to use hair compositions intended to condition the hair by providing it with cosmetic properties as well as good shaping.

However, the conditioning effect obtained by these haircare products fades quickly over time, and does not in particular exhibit satisfactory shampoo persistence.

In addition, these hair compositions have little or no effect on the control of the volume of keratin fibers and / or the maintenance of the hairstyle and / or the discipline of the hair in a humid or very humid environment (“humidity resistant shape and volume control ”). They also have little or no effect on the sensitivity to mechanical stresses such as tightening by an elastic strap or on the lack of volume of the hair near the roots.

There is therefore a real need to develop hair treatment methods which are capable of preserving or even improving the quality of the fiber such as softness, detangling, smoothing, discipline, volume, strength of the fibers. hair for example by reducing the breakage of the hair, this in a persistent manner, or by making them less sensitive to mechanical stresses such as tightening, or by making it possible to control the volume and frizz and / or the shape of the hair, or even in making volume close to the roots as well as the hairstyle in a humid environment, in particular very humid, or even by making volume to soft hair near the roots a fortiori so as to be resistant to humidity and to shampoos.

In addition, it is known that riboflavin can initiate photochemical reactions such as crosslinking of polysaccharides to form gels (see for example WO2010 / 083039, J. Biomed. Mater. Res. B Appl Biomater., Kim, S.- H., Chu, C.-C., 91 (1), 390-400 (2009).

It is also known the use of riboflavins associated with collagen and UVA to treat the cornea of the eye (see for example J Cataract Refract Surg. Feb; 36 (2): 273-6. (2010) doi: 10.1016 / j.jcrs.2009.07.041.) This association has not been used in the field of capillaries to repair hair.

There is still a need to develop a method for treating hair, more particularly a method for treating keratin fibers in an effective and lasting manner by limiting the perceived degradation of the hair, in particular residual with respect to successive shampoos and to control the shape. moisture resistant hair fibers.

There is also a need to develop a hair treatment method, more particularly an effective and if possible lasting hair treatment method by limiting the perceived degradation of the hair, in particular the perception of dry, coarse, brittle, dull, split hair and / or soft or sensitive to humidity often with frizz, and / or difficult to comb in wet conditions, in particular in very humid environments, and in particular by making them insensitive to mechanical stresses such as tightening by an elastic strap to make for example a ponytail or by giving them volume in a durable manner resistant to humidity and to shampoos, in particular near the roots. In addition, there is a real need to develop a hair treatment method which has withstood repeated shampoos of at least 5 shampoos.

This (s) goal (s) is (are) achieved by the method of the invention, i.e. a hair treatment method, comprising:

1) a step of applying a composition (A) comprising:

i) one or more flavin derivatives chosen from the following compounds of formula (I):

Ο) as well as their acid or base salts, organic or mineral, their optical, geometric isomers, tautomers, and their solvates such as hydrates; Formula (I) in which:

• R ¹ , R ² , R ³ and R ⁴ , identical or different, represent a hydrogen or halogen atom or a group chosen from hydroxy, (Ci-Ce) alkyl, (Ci-Ce) alkoxy, (CiC6 ) alkylthio, (di) (Ci-C6) (alkyl) amino, nitro (so), in particular chosen from hydrogen and (Ci-Ce) alkyl; more particularly R ¹ and R ⁴ represent a hydrogen atom, and R ² and R ³ represent a hydrogen atom or a (CiC4) alkyl group such as methyl;

• R ⁵ represents a hydrogen atom, or a (Ci-Cs) alkyl group optionally substituted by one or more groups chosen from i) hydroxy, ii) R ⁶ -C (Y ”) - O- with R ⁶ representing a hydrogen atom, a (Ci-C4) alkyl or aryl (CiC4) alkyl group such as benzyl and Y ”represents an oxygen or sulfur atom, or N (R ⁷ ) with R ⁷ representing a hydrogen atom , or a (Ci-C4) alkyl group, preferably Y ”represents an oxygen atom, iii) phosphoric (HO) 2P (O) -O, iv) -O - [(HO) P (O) -O ] _n -Suc-Hét with Suc representing a divalent sugar group such as ribose, and Hét representing a heteroaryl group such as adenine, n an integer being 0, 1, or 2, preferably 2; in particular the Suc-Hét group represents a ribose group substituted by an adenine group;

• X represents a nitrogen atom or a methylene group C (R ⁸ ) with R ⁸ representing a hydrogen atom, or a (Ci-C4) alkyl group, preferably X represents a nitrogen atom;

• X 'represents an oxygen atom or a NR ⁹ group with R ⁹ representing a hydrogen atom, or a (Ci-Ce) alkyl group, in particular X' denotes NR ⁹ preferably NH;

• Y and Y ', identical or different, represent an oxygen or sulfur atom or a group NR ¹⁰ with R ¹⁰ representing a hydrogen atom, or a (CiCe) alkyl group, preferably Y and Y' represent a oxygen atom; and ii) one or more polyamino acids; and

2) a step of energizing the hair consisting in exposing the hair to at least one artificial or natural light radiation, it being understood that steps 1) and 2) can be carried out simultaneously with the application, or sequentially, preferably simultaneously to the application or then sequentially to the application 1) then 2).

The invention also relates to a composition (B) comprising i) one or more compounds of formula (I) as defined above, ii) one or more polyamino acids and iii) one or more amines different from i) of the compounds of formula (I ), and different ii) polyamino acids preferably one or more amines chosen from the amino acids of formula (III).

The subject of the invention is also a method of treating hair using a) a step of applying a composition (B) as described above on the hair and b) a step of energizing the hair, consisting of exposing the hair to at least an arifial or natural light radiation, it being understood that steps a) and b) can be carried out simultaneously, upon application, or sequentially, preferably simultaneously with application or then sequentially with application a) then b).

The invention also relates to a kit or device with several compartments:

- either comprising in one compartment the ingredient i), and in another compartment the ingredient ii), or comprising in one compartment the ingredients i) and ii) together, and

- in another compartment a device emitting artificial light.

Another object of the invention is the cosmetic use i) of one or more compounds of formula (I) as defined above in the presence ii) of one or more polyamino acids and at least one artificial or natural light radiation ; in particular for the care and / or repair of hair.

The method of the invention implementing the application to the hair of a composition (A), or (B) containing at least one compound of formula (I) as defined above, in particular at least one derivative of riboflavin phosphate (derivative of vitamin B2), optionally an amino acid such as arginine and at least one polyamino acid, said application being followed by a step of irradiation with at least one light radiation, makes it possible to improve the cosmetic of the hair. Hair appears repaired. The hair treated by the process of the invention has more volume and in particular near the roots by a detachment effect of the roots resistant to high hygrometries and the effect being remanent with shampoos, that is to say that the hair treated by the method of the invention keeps its volume and its shape even after exposure to high humidity such as a relative humidity of 80% and that this transformation withstands repeated shampooing.

Other characteristics and advantages of the invention will appear more clearly on reading the description and the examples which follow.

In what follows unless stated otherwise:

by "se /" is meant addition salts with an acid or an organic or inorganic base;

by “se / organic or mineral acid” is meant addition salts obtained by addition of cosmetically acceptable organic or mineral acid, more particularly the salts chosen from a salt derived from i) hydrochloric acid HCl, ii) d hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S (O) 2OH such as methylsulfonic acid and ethylsulfonic acid; v) arylsulfonic acids: Ar-S (O) 2OH such as benzene sulfonic acid and toluene sulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid, x) alkoxysulfinic acids: Alk-O-S (O) OH such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; xii) phosphoric acid H3PO4; xiii) acetic acid CHsC (O) OH; xiv) triflic acid CF3SO3H andxv) tetrafluoroboric acid HBF4;

"alkyl" means a linear or branched radical containing from 1 to 12 carbon atoms, in particular from 1 to 8 carbon atoms, more particularly from 1 to 8 carbon atoms, preferably from 1 to 4 carbon atoms , for example methyl, ethyl, n-propyl, iso-propyl, butyl, npentyl, n-hexyl, preferably methyl or n-propyl and more preferably methyl;

by “(C _x -C _y ) alkyl” is meant an alkyl radical as defined above, said alkyl radical comprising x to y carbon atoms;

"alkylene" means a linear or branched divalent radical containing from 1 to 16 carbon atoms, in particular from 1 to 12 carbon atoms, preferably from 1 to 8 carbon atoms, more preferably from 1 to 6 carbon atoms. carbon, even more preferably from 1 to 4 carbon atoms, for example methylene, ethylene, n-propylene, isopropylene, butylene, n-pentylene, n-hexylene, preferably methylene;

"alkylene (C _x -C _y )" means an alkylene radical as defined above, said alkylene radical comprising x to y carbon atoms;

by alkoxy is meant an alkyl oxy group with “alkyl”, as defined above;

"alkoxy (C _x -C _y )" means an alkoxy radical as defined above, said alkoxy radical comprising x to y carbon atoms;

an “aryl” radical represents a mono or polycyclic carbon group, condensed or not, comprising from 6 to 22 carbon atoms, and of which at least one ring is aromatic; particularly the aryl radical is phenyl, biphenyl, naphthyl, indenyl, anthracenyl, or tetrahydronaphthyl, preferably phenyl;

a “heteroaryl radical” represents a mono or polycyclic group, condensed or not, comprising from 5 to 22 links, from 1 to 6 heteroatoms chosen from the nitrogen, oxygen and sulfur atoms, and of which at least one cycle is aromatic; preferably a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzoxazolyl, pyridinyl, pyrimidyl, pyrimidyl-one, benzopyrazolyl, benzotriazolylidolidolididimidolidyridolidyridylazolidylidyridolidyridylidinolidylidinolidylidinolidylidinolidylidinolidylidinolidylidinolidylidinolidylidinolidylidinolidylidinolidylidinolidylidinolidylidinolidylidinolidylidinolidylidinolidylidinolidylidinolidylidinolidone , naphthooxazolyle, naphthopyrazolyle, oxadiazolyle, oxazolyle, oxazolopyridyle, phenazinyle, phenooxazolyle, pyrazinyle, pyrazolyle, purinyle-one, purinylepyrazoyltriazyle, pyridyle, pyridinoimidazolyl, thiazidyl, tyrolol, quinolyl, pyrolyl, quinolyle, pyrolyle, quinolyle

by “sugar” or “Suc” pn means a monosaccharide group or a disaccharide group, preferably a monosaccharide, each saccharide unit (the saccharide unit in the case of a monosaccharide or each saccharide unit in the case of disaccharide) comprising a or several hydroxy groups optionally substituted with an R ”radical chosen from: i) (Ci-Ce) alkyl, (C2-Ce) alkenyl; ii) an acetyl radical; or iii) a protective group (PG) of hydroxy function (s) such as (C2-C6) alkyl (thio) carbonyl, preferably (C2-C6) alkylcarbonyl; in particular R ”represents a (CiCe) alkyl group such as methyl, or an acetyl group; said mono or disaccharide radical being linked to the rest of the molecule by a bond between the carbon atom Ci of one of the sugars of said mono or disaccharide radical, this bond possibly being anomeric a or β; It is understood that for the compounds of formula (I) as defined above when Suc represents a monosaccharide radical then it may be in pyranose form (the sugar heterocycle which constitutes it is 6-membered) or furanose (the sugar heterocycle which constitutes it is 5-membered); and when Suc represents a disaccharide radical it comprises the chain of 2 saccharides or identical or different osidic units between them which can be in furanose or pyranose form. Preferably, the disaccharide results from the chain of a saccharide unit in furanose form and of a unit in pyranose form or the chain of a saccharide unit in form of pyranose and of a unit in furanose form; whether for the monosaccharide or polysaccharide radical, each saccharide unit which may be in the levorotatory L or D dextrorotatory form, and in the anomeric form a or β;

by “polyamino acids” is meant peptides consisting of amino acids linked together by peptide linkages in particular those of formula (III) as defined below, said peptides being of variable length ranging from oligopeptides containing from 2 to a few tens of amino acids up to polypeptides containing a greater number of amino acids and which may be derived from a translation of mRNA., said peptides which may also be assembled to constitute proteins such as collagen, by "polysaccharides" is understood a polysaccharide sugar which is a polymer made up of several oses linked together by O-osidic bonds, said polymers being made up of monosaccharide units as defined above, said monosaccharide units comprising at least 5 carbon atoms, preferably 6, particularly the monosidic units are linked together in 1.4 or 1.6 as anomer a (alpha) or β (b anda), each osidic unit possibly being of L or D configuration, as well as its salts and its solvates such as the hydrates of said monosaccharides; they are more particularly polymers formed from a number of oses (or monosaccharides) having the general formula: - [C _x (H2O) _y )] _n - with x an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is inclusive between 5 and 7, preferably x = 6, and y is an integer which represents x - 1, and n is an integer greater than or equal to 2, particularly inclusive between 3 and 3000, more particularly between 5 and 2500, preferably between 10 and 2300;

by “amino mono or polysaccharide” it is meant that the monosaccharide or the polysaccharide is substituted by one or more amino group (s) NRiR ₂ ie at least one of the hydroxy groups of at least one sugar unit is replaced by a group NR1R2, with Ri and R ₂ , identical or different, representing i) a hydrogen atom, ii) an (Ci-Ce) alkyl group optionally substituted, preferably by one or more hydroxy or NH _{2 groups} , iii) an aryl group such as phenyl, iv) an aryl (Ci-C4) alkyl group such as benzyl, v) a (hetero) cyclo (C5-C7) alkyl group such as cyclohexyl, morpholinyl, piperazinyl, pyperidinyl, vi) a (hetero) cyclo group ( C5-C7) (Ci-C4) alkyl such as cyclohexylmethyl, vii) -C (Y) - (Y ') _P -R'i with Y and Y', identical or different, representing an oxygen atom, sulfur or N (R ' ₂ ), preferably oxygen, p = 0 or 1, preferably 0; and R'1 and R ' ₂ representing i) to vi) of Ri and R ₂ defined above, and in particular R'1 denoting a group (C1C6alkyl such as methyl. Preferably Ri and R ₂ represent a hydrogen atom, or (C1-C4) alkylcarbonyl group such as acetyl;

moreover, the addition salts which can be used in the context of the invention are in particular chosen from addition salts with a cosmetically acceptable base such as the basifying agents as defined below such as the hydroxides of alkali metal, alkaline- earthy like soda, potash, ammonia, amines or alkanolamines;

“heterocycle” means a mono or bicyclic group, condensed or not, preferably monocyclic, saturated or unsaturated, aromatic or not, comprising from 5 to 10 links, containing from 1 to 3 heteroatoms chosen from the nitrogen atom, oxygen and sulfur, this heterocycle being able to be substituted by one or more radicals, identical or different chosen from the alkyl, hydroxyalkyl, alkoxy radicals preferentially, according to the present invention, the saturated or unsaturated heterocycle of 5 to 8 members, preferably saturated, and more preferably is chosen from piperidyl, pyrrolidinyl, piperazinyl, and morpholinyl;

“cycloalkyl” means a mono or bicyclic hydrocarbon group, condensed or not, preferably monocyclic saturated or containing one or more non-aromatic ethylenic unsaturations, comprising from 5 to 10 members, this cycloalkyl possibly being substituted by one or more radicals, identical or different ones chosen from alkyl, hydroxyalkyl and alkoxy radicals preferably, according to the present invention, the cycloalkyl is saturated comprises from 5 to 8 members, and more preferably is chosen from cyclopentyl, and cyclohexyl;

the “heterocycle”, “cycloalkyl”, “aryl”, “heteroaryl” radicals can be substituted with at least one substituent carried by a carbon atom or heteroatom, chosen from:

an optionally substituted C1-C6 alkyl radical;

a halogen atom;

a hydroxyl group;

a C1-C2 alkoxy radical;

a C2-C4 (poly) -hydroxyalkoxy radical;

an amino radical;

a 5- or 6-membered heterocycloalkyl radical;

a 5 or 6-membered heteroaryl radical optionally substituted by an (C1-C4) alkyl radical, preferably methyl;

an amino radical substituted by one or two identical or different C1-C6 alkyl radicals optionally carrying at least:

i) a hydroxyl group, ii) an amino group optionally substituted by one or two optionally substituted C1-C3 alkyl radicals, said alkyl radicals being able to form, with the nitrogen atom to which they are attached, a heterocycle comprising from 5 to 7 chain links, saturated or unsaturated optionally substituted optionally comprising at least one other heteroatom different or not from nitrogen;

an acylamino radical (-NR-C (O) -R ') in which the radical R is a hydrogen atom, a C1-C4 alkyl radical optionally bearing at least one hydroxyl group and the radical R' is a C1-C2 alkyl radical;

a carbamoyl radical ((R) 2N-C (O) -) in which the radicals R, which may or may not be identical, represent a hydrogen atom, a C1-C4 alkyl radical optionally carrying at least one hydroxyl group;

an alkylsulfonylamino radical (R'-S (O) 2-N (R) -) in which the radical R represents a hydrogen atom, a C1-C4 alkyl radical optionally carrying at least one hydroxyl group and the radical R 'represents a C1-C4 alkyl radical, a phenyl radical; an aminosulfonyl radical ((R) 2N-S (O) 2-) in which the radicals R, which may or may not be identical, represent a hydrogen atom, a C1-C4 alkyl radical optionally carrying at least one hydroxyl group;

a carboxylic radical in acid or salified form (preferably with an alkali metal or ammonium, substituted or not);

a cyano group;

a nitro or nitroso group;

a polyhaloalkyl group, preferably trifluoromethyl;

“elastic means” means any means of tightening keratin fibers, in the form of a short wire, strip or ribbon comprising at least one part of elastic material such as rubber, of generally circular shape, the expression “at least a ”is equivalent to“ one or more ”; and the expression "inclusive" for a range of concentrations means that the limits of the range are part of the defined range

i) The flavins of formula (I)

The compositions (A), or (B) of the invention comprise at least one compound of formula (I) as defined above.

According to a particular embodiment of the invention, the compounds of formula (I) are such that R ¹ , R ² , R ³ and R ⁴ , identical or different, represent a hydrogen atom, (Ci-Ce) alkyl, (Ci-Ce) alkoxy, (di) (Ci-C4) (alkyl) amino, in particular chosen from hydrogen and (Ci-C4) alkyl. Preferably R ¹ and R ⁴ represent a hydrogen atom, and R ² and R ³ represent a hydrogen atom or a (CiC4) alkyl group such as methyl, preferably a (Ci-C4) alkyl group such as methyl ..

According to a particular embodiment of the invention, the compounds of formula (I) are such that R ⁵ represents a (Ci-Ce) alkyl group such as methyl.

According to another preferred embodiment of the invention, the compounds of formula (I) are such that R ⁵ represents a (Ci-C6) alkyl group substituted by one or more identical or different groups chosen from i) hydroxy, ii) R ⁶ -C (O) -O- with R ⁶ representing a hydrogen atom, a (Ci-C4) alkyl group such as methyl or npropyl; iii) phosphoric (HO) 2P (O) -O-, iv) -O - [(HO) P (O) -O] _n -Suc-Hét with Suc representing a monosaccharide such as ribose, and Hét representing a group optionally substituted heteroaryl, in particular optionally substituted pyrimidyl-dione such as adenine, n an integer equal to 1, or 2, preferably 2; in particular Suc-Hét represents a ribose group, preferably α-D-ribose, optionally substituted by an adenine group.

According to a preferred embodiment, the compounds of formula (I) are such that the radical Suc represents a divalent monosaccharide radical whose heterocycle which constitutes it contains 4 or 5 carbon atoms, of the following formula:

R _a representing a group (Ci-Cfialkylène such as methylene and R _a being linked to the rest of the molecule via at least one phosphate group, it being understood that the radical R _a is in position C ⁵ if the sugar motif is in the pyranose form or in C ⁴ if it is in furanose form;

Rb represents a hydrogen atom or a group -CH2-O-A; preferably

Rb denotes a hydrogen atom;

A represent a hydrogen atom, a (Ci-Ce) alkyl group, or a hydroxy protecting group such as R _c -C (O) - with R _c representing a hydrogen atom or a (Ci-Cfialkyle group that methyl, or then when n is greater than or equal to 2 and that two groups A-0 are contiguous then two groups A can together form a chain (Ci-C6) alkylene, linear or branched; preferably all the protecting groups of A are the same ;

m is 1, 2 or 3; preferably m = 2;

represents the two substitution parts of the divalent monosaccharide.

According to a more particular embodiment, the compounds of formula (I) are such that R ⁵ represents the following group:

With R _a , A, Hét and m are as defined above,

- ALK representing a (Ci-C6) alkylene group, preferably pentylene, optionally substituted by one or more hydroxy groups;

- M represents a hydrogen atom or a cationic counter ion, in particular an alkali or alkaline earth metal such as Na ⁺ , K ⁺ or ammonium, preferably Na ⁺ and representing the part which is connected to the rest of the molecule;

Preferably Het represents a purine or pyrimidine nitrogen base such as adenine, thymine, guanine, cytosine or uracil. Preferably Het represents an optionally substituted bicyclic heteroaryl group, more particularly Het represents a purinyl-dione group optionally substituted in particular by one or more (di) (Ci-C4) (alkyl) amino groups, preferentially Het is a purine nitrogen base such that l adenine.

According to a more particular embodiment, the compounds of formula (I) are such that R ⁵ represents a (Ci-Ce) alkyl group optionally substituted by one or more hydroxy or phosphate groups such as pentyl substituted by one, two, three or four hydroxy groups and optionally with a phosphate group such as 2,3,4,5-tetrahydroxypentyl or 5-dihydrogenophosphate-2,3,4-trihydroxypentyl.

According to a particular embodiment, the compounds of formula (I) are such that X represents a nitrogen atom.

According to a particular embodiment, the compounds of formula (I) are such that X 'represents a group NR ⁹ with R ⁹ representing a hydrogen atom, or a (Ci-Ce) alkyl group, in particular X' preferably denotes NH.

According to a particular embodiment, the compounds of formula (I) are such that Y and Y ’are identical, more particularly represent an oxygen or sulfur atom, preferably Y and Y’ represent an oxygen atom.

More particularly, the compounds of formula (I) of the invention are chosen from the following compounds 1 to 7:

Structure 1

(2 / ?, 3S, 4S) -5- (7,8-dimethyl-2,4-dioxo-3,4dihydrobenzo [g] pteridin-10 (2H) -yl) -2,3,4-trihydroxypentyl dihydrogen phosphate or riboflavin 5'-phosphate, or riboflavin-5'-phosphate

7,8-dimethyl-10 - ((2 / ?, 3 / ?, 4S) -2,3,4,5-tetrahydroxypentyl) benzo [g] pteridine2,4- (3H, 10H) -dione, or vitamin B2 , lactoflavin

k 0 ^ ^ 0 6 x / y0 ^ \ o 0 i y ^N y ° Y / N h ₃ c NOT 0 Riboflavin tetrabutyrate CAS # 752-56-7 CH, I ³ [ΓΎ 'Ί ^ ^N y ° 7 AA AT 0 10-methylbenzo [g] pteridine-2,4 (3H, 10H) -dione CASE = 4074-58-2

as well as their acid or base salts, organic or mineral, their optical isomers, their tautomers and their solvates such as hydrates, in particular their alkali metal salt such as sodium.

According to a particular embodiment, the compositions (A), or (B) comprise one or more compounds of formula (I) as defined above in an amount included between 0.01 and 30% by weight relative to the total weight of composition (A), or (B), in particular between 0.05 and 20%, more particularly between 0.1 and 10%, preferably between 1 and 5% by weight relative to the total weight of the compositions (A) , or (B).

ii) Polyamino acids

According to a particular embodiment of the invention the polyamino acid (s) 15 have a molecular weight greater than or equal to 1 Kilo Dalton (KDa) preferably of molecular weight greater than 2 KDa, more particularly greater than 10 KDa or even greater than 20 KDa .

In particular, the polyamino acid (s) of the invention are chosen from cytoskeletal proteins such as keratins, in particular a-keratins, such as those derived from wool, fur, claws and hair and the β keratins found and in scales and claws of reptiles, their shells and in feathers, beaks, claws of birds and porcupine quills.

The following articles can be cited for future reference: Wang, Bin (2016). Keratin: Structure, mechanical properties, occurrence in biological organisms, and efforts at bioinspiration. Progress in Materials Science. 76: 229-318.

doi: 10.1016 / j.pmatsci.2015.06.001 & Keratins: The human keratins: biology and pathology, Histochem Cell Biol. (2008) doi: 10.1007 / s00418-008-0435-6

Synthetic versions of keratins can also be used in the invention and are known to those of skill in the art. By way of example, mention may be made of US Pat. No. 4,722,895 A.

According to a preferred embodiment, the polyamino acid (s) are proteins with an extracellular matrix such as collagens. Many different types of collagen and hydrolyzed collagens are commercially available from suppliers such as Sigma-Aldrich (examples of Sigma-Aldrich trade references are C7661, 5162, C9791).

Preferably, the polyamino acid (s) of the invention comprise an amino acid sequence with glycine units (Gly - X - Y) _n and comprise one or more Gly - Pro - Hyp triplets.

Synthetic versions of collagens are also known and can be used in the invention. The scientific literature describes such synthetic versions of collagens. For example, we can cite the articles Adv Exp Med Biol. ·, 611: xci-xcviii (2009) and J. Am. Chem. Soc. 132, 13957-13959 (2010) ,.

Mention may also be made, as examples of polyamino acids of the invention, of polypeptides derived from silk proteins such as those cited in US Pat. No. 5,747,015.

Synthetic polyamino acids can also be used in the invention. These can be homopolymers based on a single amino acid, in particular of formula (III) as defined below, preferably chosen from Poly-L-proline, Poly-L-hydroxyproline, Poly-L-threonine, Polyglycine, Poly-L-serine, Poly-DL-alanine, Poly-L-glutamine, Poly-L-tyrosine, or the synthetic polyamino acids can be copolymers based on more than one amino acid. The scientific literature describes such synthetic polyamino acids.

As an example, we can cite the articles "Synthesis and Chemical Properties of Poly-a-Amino Acids, Advances in Protein Chemistry, Volume 13, 243-492, (1958)," Contribution of poly (amino acids) to advances in pharmaceutical biotechnology, Curr Pharm Biotechnol. Oct; 4 (5): 323-30 (2003); “Microbial degradation of poly (amino acid) s. Biomacromolecules. Jul-Aug; 5 (4): 1166-76 (2004); “Occurrence, functions and biosynthesis of polyamides in microorganisms and biotechnological production. Naturwissenschaften. Jan; 89 (1): 11-22 (2002).

Natural polyamino acids based on homopolymers can also be used in the invention such as gamma-glutamic acid and poly (epsilon-Llysine).

Natural polyamino acids-g-amino acids can also be used in the invention, such as cyanophycin composed of a skeleton of aspartic acid and arginine side groups.

Polyamino acids can come from many sources such as keratins (wool, hair, etc.), silk proteins, collagens, protamins, vegetable proteins (soy, oats, wheat, etc.). They can also come from extracts or hydrolysates of keratins such as gelatin.

According to a particular embodiment, the compositions (A), or (B) comprise one or more polyamino acids as defined above in an amount inclusive between 0.01 and 20% by weight relative to the total weight of composition (A) or (B), in particular between 0.05 and 10%, more particularly between 0.1 and 5%, preferably between 0.2 and 2.5%, more preferably between 0.25 and 1% by weight relative to the weight total of composition (A) or (B).

iii) Amines

Composition (B) contains i) one or more compounds of formula (I) as defined above, ii) one or more polyamino acids and iii) one or more amines different from i) of compounds of formula (I), and different ii ) polyamino acids.

According to a variant the compositions (A), contains one or more amines.

By "amines" according to the invention means any organic molecule comprising at least one primary, secondary or tertiary amine group, different i) riboflavins of formula (I), and different ii) polyamino acids. The amines can be aromatic or not, saturated or unsaturated, natural or synthetic.

According to a preferred embodiment, the amine (s) of the invention are present in the compositions (A), or (B) in an amount between 0.01% and 15% by weight relative to the total weight of the composition which comprises, more particularly between 0.1% and 10%, more preferably between 0.5% and 5% by weight relative to the total weight of the composition which comprises them.

According to a particular embodiment of the invention, the composition (A) of the invention comprises at least one amine, preferably at least one amino acid, preferably at least one natural amino acid.

According to a particular embodiment, composition B contains one or more amines chosen from amino acids, preferably from natural amino acids.

Preferably, the amino acid (s) are chosen from the compounds of formula (III) below:

H

R _a -n

OH (III) as well as their acid or base salts, organic or mineral, their optical, geometric isomers, tautomers, and their solvates such as hydrates;

Ra represents a hydrogen atom, a group a group (Ci-C4) alkyl, (CiC4) alkylcarbonyle or then forms together with the radical Rb and the atom of nitrogen and carbon which carry them respectively a heterocycle mono or bicyclic, comprising from 5 to 10 members such as pyrolidinyl, preferably Ra represents a hydrogen atom;

• Rb represents a hydrogen atom, or a (Ci-Ce) alkyl group optionally substituted by one or more groups chosen from i) -ZC (Z ') Z ”-Rc with Z, Z', and Z”, identical or different, represent an oxygen or sulfur atom, and N (Rd), Rc and Rd, identical or different, represent a hydrogen atom, or a (Ci-C4) alkyl group, preferably Z, Z ' and Z ”represent an N (Rd) group such as NH; ii) (hetero) aryl such as imidazolyl, indolyl, phenyl optionally substituted in particular by a hydroxy group; iii) (di) (Ci-C4) (alkyl) amino, iv) -C (Z ') - Z ”-Rc with Z', Z” and Rc as defined above, in particular Z 'represents an atom of oxygen, Z ”represents an oxygen atom or an N (Rd) group such as NH, and R _c represents a hydrogen atom; v) -Z '”- Rc with Z'” represents an oxygen, sulfur or selenium atom or an NH group and Rc is as defined above; in particular RB represents a (Ci-Ce) alkyl group optionally substituted by i) -ZC (Z ') - Z ”-Rc with Z, Z', and Z”, identical or different, represent an oxygen atom, of sulfur, and N (Rd), Rc and Rd, identical or different, represent a hydrogen atom, or a group (Ci-Cfialkyle, preferably Z, Z 'and Z ”represent an N (Rd) group such as NH ;

where Ra and Rb form together with the nitrogen atom which carries Ra and with the carbon atom which carries Rb a saturated 5 or 6-membered heterocycle, preferably 5-membered, such as a pyrrolidine ring.

Said amino acids of formula (III) can be of configuration L (levogyre) or D (dextrogyre) or in mixture, preferably of configuration L.

In particular, the amino acid or acids are chosen from alanine, arginine, proline, preferably L-alanine, L-arginine, L-proline, in particular L-arginine or Lproline, more preferably L -arginine.

According to a preferred embodiment, the amino acid (s) of formula (III) of the invention are present in the composition (A) or in the composition (B) in an amount between 0.01% and 15% by weight relative to to the total weight of the composition which comprises them, more particularly between 0.05% and 10%, more preferably between 0.1% and 5% by weight relative to the total weight of the composition which comprises them.

According to another particular embodiment of the invention, the composition (A) or (B) of the invention comprises at least one amine comprising an optionally substituted (hetero) aryl group, in particular of formula (IV):

CYC- (ALK) p-NR _e Rf as well as their acid salts, organic or mineral, their optical isomers, and their solvates such as hydrates;

Formula (IV) in which:

• CYC representing an optionally substituted heterocycle, cycloalkyl, aryl or heteroaryl group, preferably aryl such as phenyl, • ALK representing an (Ci-C6) alkylene group, • R _e and Rf, identical or different, representing a hydrogen atom , a (Ci-Ce) alkyl group; and • p is 0 or 1.

Preferably the compounds of formula (IV) are a benzylamine.

According to a preferred embodiment, the amine or amines of formula (IV) are present in the composition (A) or in the composition (B) in an amount between 0.01% and 20% by weight relative to the total weight of the composition. which comprises them, more particularly between 0.05% and 10%, more preferably between 0.05% and 5% by weight relative to the total weight of the composition which comprises them.

Alcohols

According to a particular embodiment, the composition (A) or the composition (B) as defined above contains at least one alcohol.

According to a particular embodiment of the invention, the compositions (A) or (B) of the invention comprise at least one alcohol comprising an optionally substituted (hetero) aryl group, in particular of formula (IV ’):

CYC- (X) q- (ALK) _p -OH (IV ')

As well as their acid or base salts, organic or mineral, their optical isomers, and their solvates such as hydrates;

Formula (IV ’) in which:

CYC representing a heterocycle, cycloalkyl, aryl or heteroaryl group optionally substituted in particular by one or more (Ci_C4) alkyl or (di) (Ci-C4) (alkyl) amino groups, preferably aryl such as phenyl or cycloalkyl such as cyclohexyl, • ALK representing a (Ci-C6) alkylene group, • p and q, identical or different, are 0 or 1, it being understood that when p is 0 then q is 0 and that p is 1 when q is 1.

Preferably, the compounds of formula (IV ’) are chosen from benzyl alcohol, phenoxyethanol, and alcohol / V, / V-dimethylaminobenzyl.

According to another preferred embodiment of the invention, the alcohols are chosen from terpenes, more preferably chosen from menthol, isoborneol, and neomenthol.

According to another particular embodiment, the alcohols are chosen from (Ci-Ce) alkanols, linear or branched, saturated or unsaturated, such as isopropanol.

According to another more specific embodiment of the invention, the composition (A) or (B) of the invention comprises at least one alcohol comprising an optionally substituted (hetero) aryl group, in particular of formula (IV ”):

ReRfN- (ALK ') _p - CYC- (ALK) _P -OH as well as their acid or base salts, organic or mineral, their optical isomers, and their solvates such as hydrates;

Formula (IV) in which:

• CYC representing an optionally substituted heterocycle, cycloalkyl, aryl or heteroaryl group, preferably aryl such as phenyl, • ALK and ALK 'independently representing an (Ci-C6) alkylene group, • R _e and Rf, identical or different, representing a hydrogen atom, a (Ci-Ce) alkyl group such as methyl; and • p and p 'are independently 0 or 1.

Preferably the compounds of formula (IV ”) are chosen from an N, Ndimethylamino benzyl alcohol.

According to a preferred embodiment, the alcohol (s) in particular the aclool (s) of formula (IV ') or (IV ”) are present in the compositions (A) or (B) in an amount of between 0.01% and 20% by weight relative to the total weight of the composition which comprises them, more particularly comprised between 0.05% and 10%, more preferably comprised between 0.05% and 5% by weight relative to the total weight of the composition which comprises them.

According to a preferred embodiment of the invention, the compositions (A) or (B) comprise one or more amines, in particular amino acids of formula (III), and one or more alcohols as defined above in an amount included between 0 , 01 and 30% by weight relative to the total weight of the composition (A) or (B), in particular between 0.05 and 20%, more particularly between 0.1 and 10%, preferably between 1 and 5% in weight relative to the total weight of the compositions (A) or (B).

Stage 2) - the stage of energy supply by light radiation

According to the method of the invention, step 2) comprises exposing the hair to at least one artificial and / or natural light radiation which may be continuous or non-continuous before, during or after application of the compositions (A), or ( B) as defined above on said hair.

According to the method of the invention, step 2) comprises in particular the exposure of the hair to at least one artificial and / or natural light radiation which may be continuous or non-continuous before, during or after application of the compositions (A) or (B) as defined above on said hair.

For the purposes of the invention, the term "artificial light radiation" means light radiation different from natural daylight (generated by the sun). In other words, natural daylight (generated by the sun) is not artificial light radiation.

By "natural radiation" is meant radiation whose only light source is that of the day generated by the sun.

Preferably, the exposure of the keratin fibers to artificial light radiation is carried out at a wavelength between 360 and 600 nm, preferably between 375 and 550 nm, more preferably between 400 and 480 nm.

Preferably, the artificial light radiation has an amount of energy per unit area greater than or equal to 1 J / cm ² , more preferably strictly greater than 1 J / cm ² , more preferably still between 1.001 and 100 J / cm ² , even better between 2 and 50 J / cm ² , particularly preferred between 3 and 10 J / cm ² .

Preferably, the artificial light radiation is generated using a device chosen from arc lamps such as xenon lamps and mercury lamps, fluorescent lamps, incandescent lamps such as halogens, light-emitting diodes (LEDs), organic light-emitting diodes (LEDs), lasers.

For example, we can cite the goLITE BLU from the company Philips, the Energylight HF 3319/01 lamp from the company Philips, the Dayvia White and Messa lamps from the company Solvital, the Lumino Plus lamp from the company Lanaform , the medibeam lamp from Medibeam, the M-LED 01 lamp from Meimed, the Lifemax light pod lamp from Lifemax, the Lite-Pad lamp from Reicorp, the Omnilux Clear-U and New-U lamps from Omnilux, the 1000W Arc Xenon lamp from Lot-Oriel and the Camag Box 3 (4x8W) lamp from Camag.

Preferably, the duration of exposure of the hair to artificial or natural light radiation is greater than or equal to 5 seconds, more preferably between 10 seconds and 60 minutes, more preferably still between 15 seconds and 50 minutes, even better between 20 seconds and 40 minutes.

According to a variant of the invention, the invention relates to a method for treating hair, comprising:

1) a step of applying a composition (A) comprising:

i) one or more compounds of formula (I) as defined above, and ii) one or more polyamino acids as defined above;

2) a step of energizing said hair consisting in exposing the hair to at least one artificial or natural light radiation as defined above, steps 1) and 2) being able to be carried out simultaneously, or separately, preferably simultaneously or then separately 1) then 2).

According to a particular embodiment of the invention, the hair treatment method of the invention implements at the same time (simultaneously) the steps

1 and 2).

According to a variant at the same time as the application of the composition (A), on the hair, said hair is exposed to at least one artificial and / or natural light radiation.

According to a particular embodiment of the invention, when steps 1) and

2) of the process are carried out simultaneously, the duration of exposure of the hair to at least one artificial and / or natural light radiation is between 5 seconds and 3 hours, preferably between 1 minute and 1 hour, more preferably between 5 minutes and 30 minutes such as 20 minutes; optionally followed by a step of rinsing said hair.

According to a preferred embodiment of the invention, when step 2) is implemented after step 1), the duration of exposure of the hair to artificial or natural light radiation is between 5 seconds and 3 hours , preferably between 1 minute and 1 hour, more preferably between 5 minutes and 30 minutes such as 20 minutes.

According to a variant of the invention when step 2) of the method is implemented after step 1), an intermediate laying step can follow step 1) before implementation of step 2).

The step of laying the composition (A) or (B) on the hair is carried out for a period of between 5 seconds and 3 hours, preferably between 1 minute and 1 hour such as 20 minutes, this laying step being put implemented between step 1) and step 2); optionally a hair rinsing step is carried out after step 2).

According to another preferred embodiment of the method, when step 2) is implemented after step 1), the duration of exposure of the hair to artificial or natural light radiation is between 5 seconds and 3 hours, preferably between 1 minute and 1 hour such as 20 minutes; said process possibly comprising a step of applying composition (A), or (B) to the hair for a period of between 5 seconds and 3 hours, preferably between 1 minute and 1 hour such that 15 minutes is carried out between step 1) and step 2); and a step of rinsing said keratin fibers is carried out after step 1).

According to a variant of the invention, the invention relates to a method for treating hair, comprising:

1. a step of applying a composition (B) comprising:

at. one or more compounds of formula (I) as defined above,

b. one or more identical or different amines of formula (III) as defined above,

vs. one or more polyamino acids as defined above;

d. optionally one or more alcohols as defined above, preferably chosen from the alcohols of formula (IV ’) and / or (IV”):

1i) then optionally an exposure time as defined above;

2. a step of energizing said hair consisting in exposing the hair to at least one artificial or natural light radiation as defined above,

2i) then optionally a step of rinsing the hair steps 1) and 2) which can be carried out simultaneously, or separately, preferably simultaneously or then separately 1) then 2), or 1) then 1i) then 2) then optionally 2i).

According to a particular embodiment of the invention, the hair treatment method of the invention implementing the composition (B) implements at the same time (simultaneously) steps 1) and 2).

According to a variant at the same time as the application of the composition (B), on the hair, said hair is exposed to at least one artificial and / or natural light radiation.

According to a particular embodiment of the invention, when steps 1) and 2) of the method implementing the composition (B) are implemented simultaneously, the duration of exposure of the hair to at least one artificial light radiation and / or natural is between 5 seconds and 3 hours, preferably between 1 minute and 1 hour such as 20 minutes; optionally followed by a step of rinsing said keratin fibers.

According to a preferred embodiment of the invention implementing the composition (B), when step 2) is implemented after step 1), the duration of exposure of the hair to artificial or natural light radiation is between 5 seconds and 3 hours, preferably between 1 minute and 1 hour such as 15 minutes and the method optionally comprises a step of applying the composition (B) to the hair for a period of between 5 seconds and 3 hours, preferably between 1 minute and 1 hour such as 20 minutes, this laying step being carried out between step 1) and step 2), the method optionally comprising a step of rinsing the hair carried out after step 2 ).

According to another preferred embodiment of the invention implementing the composition (B), when step 2) is implemented after step 1), the duration of exposure of the hair to artificial light radiation or natural is between 5 seconds and 3 hours, preferably between 1 minute and 1 hour such as 20 minutes; and the method optionally comprises a step of laying the composition (B) on the hair for a period of between 5 seconds and 3 hours, preferably between 1 minute and 1 hour such as 15 minutes, this laying step being carried out between step 1) and step 2); the method optionally comprising a step of rinsing the hair carried out after step 1).

According to a variant of the invention, the invention relates to a method for treating hair, comprising:

1) a step of applying a composition (A) comprising:

at. one or more compounds of formula (I) as defined above;

b. optionally one or more identical or different amines preferably chosen from the amines of formula (III) and / or (IV) as defined above, preferably chosen from the amines of formula (III);

vs. one or more polyamino acids as defined above;

d. optionally one or more alcohols as defined above, preferably chosen from the alcohols of formula (IV) and / or (IV ”):

1i) then optionally an exposure time as defined above;

2) a step of energizing said hair consisting in exposing the hair to at least one artificial or natural light radiation as defined above,

2i) then optionally a step of rinsing the hair, steps 1) and 2) can be carried out simultaneously, or separately, preferably simultaneously or then separately 1) then 2), or 1) then 1i) then 2) then optionally 2i ).

The compositions (A), or (B) of the invention can be applied to dry or wet hair, preferably to dry hair.

The bath ratio of the compositions applied can vary from 0.1 to 10, more particularly from 0.2 to 5, and preferably between 0.5 and 3. By bath ratio is meant the ratio between the total weight of the applied composition and the total weight of hair to be treated.

In particular, the step of applying the composition (A), or (B) to the hair can be followed by an exposure time. The exposure time, namely the contact time of the composition (A) or (B) on the hair is preferably at least 5 minutes, preferably between 10 and 60 minutes, preferably between 15 and 45 minutes.

Rinsing of the hair may possibly be provided after the application of the composition (A), or (B) and optionally after the application time.

The hair can then be towel-dried or not, preferably towel-dried.

Hair treatment method

According to a variant, the method of the invention is implemented on damaged, discolored or sensitized hair.

According to a particular form of the invention, the method of the invention is a method of treating hair, comprising

1) a step of applying to dry or damp hair one or more compounds of formula (I) as described above, or of a composition (A), containing the compound or compounds of formula (I), optionally in the presence of one or more amines such as the amines of formula (III) and / or one or more alcohol (s) as defined above; then

1i) optionally a step of laying on the hair, preferably for at least 1 minute, preferably for a period of between 5 and 60 minutes, more preferably between 10 and 45 minutes; then

1ii) possibly a spin then

1iii) possibly with drying in ambient air or with a heating device delivering a heat less than or equal to 80 ° C. using for example a helmet, a hair dryer, then

2) a step of providing energy to said hair consisting in exposing the hair to at least one artificial or natural light radiation; then

2i) a rinsing step.

According to a particular form of the invention, the method of the invention is a method of treating hair, comprising

3) a step of applying to dry or damp hair one or more compounds of formula (I) as described above, or of a composition (B) containing the compound or compounds of formula (I), in the presence one or more amines of formula (III) and / or one or more alcohol (s) as defined above; then

1i) optionally a step of laying on the hair, preferably for at least 1 minute, preferably for a period of between 5 and 60 minutes, more preferably between 10 and 45 minutes; then

1ii) possibly a spin then

1iii) possibly with drying in ambient air or with a heating device delivering a heat less than or equal to 80 ° C. using for example a helmet, a hair dryer, then

4) a step of energizing said hair consisting in exposing the hair to at least one artificial or natural light radiation; then

2i) a rinsing step.

According to another variant, the method is implemented on natural hair, that is to say having not undergone any chemical treatment such as coloring, bleaching or a perm.

The compositions (A), or (B) / es compositions

The composition (s) of the invention are cosmetic, ie contain a physiologically acceptable medium, that is to say compatible with the keratin materials of human beings such as the skin (body, face, eye area, scalp), hair, eyelashes, eyebrows, body hair, nails, lips.

The physiologically acceptable medium of the composition or compositions used in the process according to the invention is advantageously an aqueous medium. It can for example consist of water or a mixture of water and at least one cosmetically acceptable organic solvent. Mention may be made, as organic solvent, of lower C2-C4 alcohols, such as ethanol and isopropanol; polyols, in particular those having from 2 to 6 carbon atoms such as glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol; polyol ethers such as 2-butoxyethanol, propylene glycol monomethyl ether, monoethyl ether and diethylene glycol monomethyl ether; and their mixtures.

The cosmetic compositions of the invention are preferably aqueous and then comprise water at a concentration ranging from 5 to 99.9%, better still from 30 to 99%, even better still from 50 to 98% by weight relative to the weight total of the composition, and even more preferably from 60 to 98% by weight relative to the total weight of the composition.

The composition used according to the invention may also contain one or more cosmetic additives chosen from nonionic, anionic, cationic and amphoteric surfactants, vitamins and pro-vitamins different from the compounds of formula (I) including panthenol , fillers, coloring matters, pearlescent agents, opacifying agents, sequestering agents, film-forming polymers, cationic, anionic or neutral polymers, associative polymers, plasticizing agents, silicones, thickening agents, oils, defoamers, moisturizers, emollients, penetrating agents, perfumes and preservatives; preferably one or more nonionic, anionic, cationic and amphoteric surfactants, cationic, anionic, neutral polymers, or associative polymers.

Depending on their nature and the purpose of the composition, the usual cosmetic ingredients can be present in usual amounts, easily determinable by a person skilled in the art, and which can be understood, for each ingredient, between 0.01 to 80% by weight . A person skilled in the art will take care to choose the ingredients entering into the composition, as well as their quantities, so that they do not harm the properties of the compositions of the present invention.

These compositions can be packaged in pump dispensers or in aerosol containers, in order to ensure application of the composition in vaporized form (lacquer) or in the form of foam. Such forms of packaging are indicated, for example, when it is desired to obtain a spray or a foam, for the treatment of hair. In these cases, the composition preferably comprises at least one propellant.

pH of the compositions:

The pH of the compositions (A), or (B) is preferably between 3 and 10, more particularly around the neutrality between 6 and 8 such as 7.

The pHs can be adjusted by an organic or mineral acid, or by an alkaline agent chosen from mineral or organic or hybrid alkaline agents or their mixtures.

By “organic acid” is meant an acid ie a compound capable of releasing a cation or proton H ⁺ , or HsO ⁺ in aqueous media, which comprises at least one hydrocarbon chain in C1-C20, optionally unsaturated, linear or branched, a group (hetero) cycloalkyl, or (hetero) aryl and at least one acidic chemical function being in particular chosen from carboxy C (O) OH, sulphonic SO3H, sulfinic SO ₂ H, and phosphonic PO3H, phosphinic PO2H2.

More particularly, the acids used are chosen from hydrochloric acid HCl, hydrobromic acid HBr, sulfuric acid H2SO4, alkylsulfonic acids: (Ci-Ce) Alk-S (O) 2OH such as methylsulfonic acid and ethylsulfonic acid; arylsulfonic acids: Ar-S (O) 2OH such as benzene sulfonic acid and toluene sulfonic acid; (C 1 -C 6) alkoxysulfinic acids: Alk-O-S (O) OH such as methoxysulfinic acid and ethoxysulfinic acid; aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; phosphoric acid H3PO4; triflic acid CF3SO3H and tetrafluoroboric acid HBF4 and the carboxylic acid (s) of formula (D) below (D)

Formula (D) or a salt thereof in which:

A represents a monovalent group when t is worth 0 or polyvalent when t is greater than or equal to 1, hydrocarbon comprising from 1 to 50 carbon atoms, saturated or unsaturated, cyclic or non-cyclic, aromatic or non-aromatic, optionally interrupted by one or more heteroatoms and / or optionally substituted in particular by one or more hydroxy groups; preferably A represents a monovalent (Ci-Ce) alkyl or polyvalent (Ci-C6) alkylene group optionally substituted by one or more hydroxy groups.

Particularly the carboxylic acids (s) of formula (D) as defined above and preferably the acid or acids used is or are an alpha hydroxy acid such as lactic, glycolic, tartaric or citric acids.

The mineral alkaline agent (s) are preferably chosen from ammonia, alkali carbonates or bicarbonates such as sodium or potassium carbonates and sodium or potassium bicarbonates, sodium or potassium hydroxides or their mixtures.

According to an advantageous embodiment of the invention, the alkaline agent (s) are organic amines, i.e. they contain at least one substituted or unsubstituted amino group.

The organic alkaline agent (s) are more preferably chosen from organic amines whose pKb at 25 ° C is less than 12, and preferably less than 10, even more advantageously less than 6. It should be noted that these are pKb corresponding to the highest basicity function.

Mention may be made, as hybrid compounds, of the salts of the amines mentioned above with acids such as carbonic acid, hydrochloric acid.

The organic alkaline agent (s) are for example chosen from alkanolamines, oxyethylenated and / or oxypropylenated ethylenediamines, amino acids and the compounds of formula (E) below:

Formula (E) in which:

• W is a divalent C1-C6 alkylene radical optionally substituted by a hydroxyl group or a C1-C6 alkyl radical, and / or optionally interrupted by one or more heteroatoms such as oxygen or NR ^U ;

• R ^x , R ^y , R ^z R 'and R ^u , identical or different, represent a hydrogen atom, a C1-C6 alkyl or C1-C6 hydroxyalkyl, C1-C6 aminoalkyl radical.

Preferably, the alkanolamine is ethanolamine (or monoethanolamine).

In a variant of the invention, the composition comprises, as alkaline agent, one or more alkanolamines (preferably ethanolamine) and ammonia. In this variant, the alkanolamine (s) are present in a majority amount relative to the ammonia.

The following examples serve to illustrate the invention without, however, being limiting in nature.

EXAMPLES

Example 1

i. Preparation of the compositions

Ingredient Provider Riboflavin 5'-monophosphate sodium knows how to hydrate Sigma Aldrich - Reference: F6750 L-Arginine Sigma Aldrich - Reference: A5006 collagen Sigma Aldrich - Reference: C7661 Water at pH 7 Dulbeco - Reference: 14190-094

Preparation of wicks

g% in formulas Wick no. Riboflavin 5'monophosphate sodium knows how to hydrate L- arginine collagen Water at pH 7 Irradiation 1 - - Yes 2 - - No 3 - Qsp 100 Yes 4 - Qsp 100 No 5 0.5 Qsp 100 Yes 6 0.5 Qsp 100 No 7 2 - Qsp 100 Yes 8 2 - Qsp 100 No 9 0.5 - - Qsp 100 Yes 10 0.5 Qsp 100 No 11 (invention) 0.5 2 0.5 Qsp 100 Yes 12 0.5 2 0.5 Qsp 100 No

2g of formula 1 to 12 were applied to locks of dry hair (2.7g, 20cm in length, hair damaged with discoloration to have an alkaline solubility (SA) value of 20).

Wicks 1, 3, 5, 7, 9 and 11 were combed and then coated with a transparent plastic film to limit the evaporation of water, left to stand for 15 minutes and then irradiated for 20 minutes (turning the wick after 10 minutes to irradiate the face below). The plastic film was removed before rinsing thoroughly with tap water at 37 ° C for 15 seconds; the locks were shampooed with a 2% lauryl sulfate solution (0.4g of shampoo / g of hair) by kneading the locks from root to tip between the two fingers 10 times, then rinsed thoroughly with water. tap for 15 seconds, wrung between 2 sheets of absorbent paper, combed and then dried This shampoo protocol consisting of rinsing, shampooing, rinsing, wringing, wringing and then drying was repeated 4 times.

Wicks 2, 4, 6, 8, 10 and 12 were combed and then coated with a transparent plastic film to limit the evaporation of water, then coated in aluminum foil to protect from light and then left to stand protected from light for 35 minutes. The aluminum foil and plastic film were removed and the wicks were rinsed thoroughly with tap water at 37 ° C for 15 seconds, before being shampooed with a 2% lauryl sulfate solution (0.4g shampoo / g of hair) by kneading the locks from root to tip between the two fingers 10 times, rinsed thoroughly with tap water for 15 seconds, wrung between 2 sheets of absorbent paper, combed and then dried. This shampoo protocol consisting of rinsing, shampooing, rinsing, wringing, combing and then drying was repeated 4 times.

Evaluation

Root peel test

The wicks were held vertically with the root at the bottom and the distance between the root and the highest point of the wick was measured.

The highest point of the wick is the highest point of the wick before it bends to fall by gravity.

The capacity of a hair treatment to hold the lock vertically is indicative of the capacity of the treatment to detach the root and therefore give volume to the hair.

Root detachment is calculated using the formula:

% detachment (cm) = 100 x (initial detachment (tOh) in cm of the treated wick initial detachment (tOh) in cm of the untreated wick).

The higher the value "% detachment", the greater the detachment of the root.

Resistance to humidity

All the locks held vertically by the root were placed in a glove box (closed box) with a relative humidity controlled at 80%. The distance between the root and the highest point of the wick was measured immediately (at T0) and after 3 hours at 80% relative humidity (T3h).

The smaller the difference between TO and T3h, the better the humidity resistance and the better the volume control of hair with high humidity.

The greater the difference between TO and T3h, the poorer the resistance to humidity, which characterizes the absence of volume control for hair with high humidity.

If the distance between the root and the highest point of the wick after 3h has not changed compared to the initial state TO, then the treatment is considered resistant to high humidity and therefore satisfactory.

Results

i) Detachment of the root

Wick no. Separation at TO (cm) % Root Peel 1 1.0 0 2 1.0 0 3 1.0 0 4 1.0 0 5 1.1 10 6 1.1 10 7 1.0 0 8 1.0 0 9 1.0 0 10 1.0 0 11 1.4 40 12 1.1 10

ii) Moisture resistance test

Only the examples showing root detachment were evaluated.

Wick no. Separation at T0 (cm) Peel off at T3h (cm) Difference (cm) 5 1.1 0.8 0.3 6 1.1 0.8 0.3 11 1.4 1.4 0 12 1.1 0.8 0.3

Conclusion

The wick 11 of the invention shows a very good detachment of the root as well as a very good resistance to humidity.

The wick 11 of the invention was washed 5 times (like all the other wicks) before making the evaluation (root peeling test and resistance to humidity) which demonstrates that the treatment 11 of the invention is also resistant to repeated washing 10 such as 5 shampoos. .

Claims (15)

1. Hair treatment method, comprising: 1) a step of applying a composition (A) comprising: i) one or more flavin derivatives chosen from the following compounds of formula (I): O) as well as their acid or base salts, organic or mineral, their optical, geometric, tautomeric isomers, and their solvates such as hydrates; Formula (I) in which: • R ¹ , R ² , R ³ and R ⁴ , identical or different, represent a hydrogen or halogen atom or a group chosen from hydroxy, (Ci-Ce) alkyl, (Ci-Ce) alkoxy, (CiC6 ) alkylthio, (di) (Ci-C6) (alkyl) amino, nitro (so), in particular chosen from hydrogen and (Ci-Ce) alkyl; more particularly R ¹ and R ⁴ represent a hydrogen atom, and R ² and R ³ represent a hydrogen atom or a (CiC4) alkyl group such as methyl; • R ⁵ represents a hydrogen atom, or a (Ci-Cs) alkyl group optionally substituted by one or more groups chosen from i) hydroxy, ii) R ⁶ -C (Y ”) - O- with R ⁶ representing a hydrogen atom, a (Ci-C4) alkyl or aryl (CiC4) alkyl group such as benzyl and Y ”represents an oxygen or sulfur atom, or N (R ⁷ ) with R ⁷ representing a hydrogen atom , or a (Ci-C4) alkyl group, preferably Y ”represents an oxygen atom, iii) phosphoric (HO) 2P (O) -O, iv) -O - [(HO) P (O) -O ] _n -Suc-Hét with Suc representing a divalent sugar group such as ribose, and Hét representing a heteroaryl group such as adenine, n an integer being 0, 1, or 2, preferably 2; in particular the Suc-Hét group represents a ribose group substituted by an adenine group; • X represents a nitrogen atom or a methylene group C (R ⁸ ) with R ⁸ representing a hydrogen atom, or a (Ci-C4) alkyl group, preferably X represents a nitrogen atom; • X 'represents an oxygen atom or a NR ⁹ group with R ⁹ representing a hydrogen atom, or a (Ci-Ce) alkyl group, in particular X' denotes NR ⁹ preferably NH; • Y and Y ', identical or different, represent an oxygen or sulfur atom or a group NR ¹⁰ with R ¹⁰ representing a hydrogen atom, or a (CiCe) alkyl group, preferably Y and Y' represent a oxygen atom; and ii) one or more polyamino acids; and 2) a step of energizing the hair consisting in exposing the hair to at least one artificial or natural light radiation, it being understood that steps 1) and 2) can be carried out simultaneously with the application, or sequentially, preferably simultaneously to the application or then sequentially to the application 1) then 2). 2. Method according to the preceding claim in which the compound or compounds of formula (I) are such that R ¹ , R ² , R ³ and R ⁴ , dental or different, represent a hydrogen atom, (Ci-Ce) alkyl , (Ci-Ce) alkoxy, (di) (CiC4) (alkyl) amino, in particular chosen from hydrogen and (Ci-C4) alkyl; preferably R ¹ and R ⁴ represent a hydrogen atom, and R ² and R ³ represent a hydrogen atom or a (Ci-C4) alkyl group such as methyl, preferably a (Ci-C4) alkyl group such than methyl. 3. Method according to any one of the preceding claims, in which the compound or compounds of formula (I) are such that R ⁵ represents a hydrogen atom or a (Ci-Ce) alkyl group such as methyl. 4. Method according to any one of claims 1 or 2 wherein the compound or compounds of formula (I) are such that R ⁵ represents a group (Ci-Ce) alkyl substituted by one or more identical or different groups chosen from i) hydroxy , ii) R ⁶ -C (O) -O- with R ⁶ representing a hydrogen atom, a (CiC4) alkyl group such as methyl or n-propyl; iii) phosphoric (HO) 2P (O) -O-, iv) -O [(HO) P (O) -O] _n -Suc-Hét with Suc representing a monosaccharide such as ribose, and Het representing an optionally substituted heteroaryl group, in particular optionally substituted pyrimidyl-dione that adenine, n an integer 1, or 2, preferably 2; in particular Suc-Hét represents a ribose group, preferably α-D-ribose, optionally substituted by an adenine group. 5. Method according to any one of the preceding claims, in which the compound or compounds of formula (I) are as taken together or separately X represents a nitrogen atom; X 'represents a group NR ⁹ with R ⁹ representing a hydrogen atom, or a (Ci-Ce) alkyl group, in particular NR ⁹ of Preferably NH; and Y and Y ’are identical, more particularly represent an oxygen or sulfur atom, preferably Y and Y’ represent an oxygen atom. 6. Method according to any one of the preceding claims, in which the compound or compounds of formula (I) are chosen from compounds 1 to 7 Next 10: Structure OH HO ^ / P = O HO ,, A * OH I ^^ OH ^Η 3θγ ^ γ ^Ν γ ^Ν γΟ JL xj \ J \ / NH h ₃ c '^^ n γ 0 (2R, 3S, 4S) dihydrogen phosphate -5- (7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo [g] pteridin-10 (2H) -yl) -2,3,4-trihydroxypentyl or 5'-riboflavin phosphate, or riboflavin-5'-phosphate 1 2 CH, I ^{3 Η} 3θγ ^ r: 5 H, C ^ AT 0 7,8,10-trimethylbenzo [g] pteridine-2,4 (3H, 10H) -dione O O / - ^ 0 0. _X O 6 0 O ^H 3 ^C \ ^ \ i ^ ^Ν γ ° h ₃ c NOT Y 0 Riboflavin tetrabutyrate CH, I ³ [ΓΎ 'Ί ^ ^N y ° 7 AA AT O 10-methylbenzo [g] pteridine-2,4 (3H, 10H) -dione as well as their acid or base salts, organic or mineral, their optical isomers, their tautomers and their solvates such as hydrates, in particular their alkali metal salt such as sodium. 5 7. Method according to any one of the preceding claims, in which the compound (s) of formula (I) are present in an amount inclusive between 0.01 and 30% by weight relative to the total weight of the composition (A), (B ) or (B '), in particular between 0.05 and 20%, more particularly between 0.1 and 10%, preferably between 1 and 5% by weight relative to the total weight of the 10 composition (A) or (B). 8. Method according to any one of the preceding claims, in which ii) the polyamino acid (s) have a molecular weight greater than or equal to 1 Kilo Dalton (KDa), preferably of molecular weight greater than 2 KDa, more particularly greater than 10 KDa, better still at 20 KDa. 9. Method according to any one of the preceding claims, in which ii) the polyamino acid (s) are chosen from: • cytoskeletal proteins such as keratins, in particular akeratins, such as those derived from wool, fur, claws and hair and the β-keratins found in the nails and in the scales and claws of reptiles, their shells and in feathers, beaks, claws of birds and porcupine quills, • synthetic keratins; • polyamino acids which contain an amino acid sequence with glycine units (Gly - X - Y) _n and include one or more Gly - Pro Hyp triplets such as collagens; • polyamino acids derived from silk or silk proteins; • synthetic polyamino acids, in particular homopolymers based on a single amino acid, preferably chosen from Poly-L-proline, Poly-Lhydroxyproline, Poly-L-threonine, Polyglycine, Poly-L-serine, Poly-DL-alanine, Poly -L-glutamine, Poly-L-tyrosine, or the synthetic polyamines can be copolymers based on more than one amino acid; • natural polyamino acids based on homopolymers such as gamma-glutamic polyacid and poly (epsilon-L-lysine); • natural polyamino-g-amino acids such as cyanophycin composed of a skeleton of aspartic acid and arginine side groups. ; preferably the polyamino acids are chosen from keratins (wool, hair, etc.), silk proteins, collagens, protamines, vegetable proteins (soya, oats, wheat, etc.), keratin extracts or hydrolysates such as gelatin. 10. Method according to any one of the preceding claims, in which the polyamino acid (s) are present in an amount inclusive between 0.01 and 20% by weight relative to the total weight of the composition (A), in particular between 0.01 and 20% by weight relative to the total weight of composition (A) or (B), in particular between 0.05 and 10%, more particularly between 0.1 and 5%, preferably between 0.2 and 2.5%, more preferably between 0.25 and 1% by weight relative to the total weight of the composition (A). 11. Method according to any one of the preceding claims, in which the composition (A) comprises one or more different amines i) riboflavins of formula (I), and different ii) polyaminoacids; said amines possibly being aromatic or not, saturated or unsaturated, oligomeric or polymeric, natural or synthetic, preferably the amine (s) are amino acids, chosen from the compounds of formula (III) below: H R _a -n OH (III) As well as their acid or base salts, organic or mineral, their optical, geometric isomers, tautomers, and their solvates such as hydrates; • Ra represents a hydrogen atom, a group a group (Ci-Cfialkyle, (CiCfialkylcarbonyle or then forms together with the radical Rb and the nitrogen and carbon atom which carry them respectively a mono or bicyclic heterocycle, comprising 5 to 10 chain members such as pyrolidinyl, preferably Ra represents a hydrogen atom; • Rb represents a hydrogen atom, or a (Ci-Ce) alkyl group optionally substituted by one or more groups chosen from i) -ZC (Z ') Z ”-Rc with Z, Z', and Z”, identical or different, represent an oxygen atom, of sulfur, and N (Rd), Rc and Rd, identical or different, represent a hydrogen atom, or a group (Ci-Cfialkyle, preferably Z, Z 'and Z ”Represent an N (Rd) group such as NH; ii) (hetero) aryl such as imidazolyl, indolyl, phenyl optionally substituted in particular by a hydroxy group; iii) (di) (Ci-C4) (alkyl) amino, iv) -C (Z ') - Z ”-Rc with Z', Z” and Rc as defined above, in particular Z 'represents an atom of oxygen, Z ”represents an oxygen atom or an N (Rd) group such as NH, and R _c represents a hydrogen atom; v) -Z '”- Rc with Z'” represents an oxygen, sulfur or selenium atom or an NH group and Rc is as defined above; in particular RB represents a (Ci-Ce) alkyl group optionally substituted by i) -ZC (Z ') - Z ”-Rc with Z, Z', and Z”, identical or different, represent an oxygen atom, of sulfur, and N (Rd), Rc and Rd, identical or different, represent a hydrogen atom, or a (Ci-C4) alkyl group, preferably Z, Z 'and Z ”represent an N (Rd) group such than NH; where Ra and Rb form together with the nitrogen atom which carries Ra and with the carbon atom which carries Rb a saturated 5 or 6-membered heterocycle, preferably 5-membered, such as a pyrrolidine ring. 12. Method according to any one of the preceding claims, in which step 2) of energy supply consists in exposing the keratin materials to artificial light radiation at a wavelength between 360 and 600 nm, preferably between 375 and 550 nm, more preferably between 400 and 480 nm; preferably, the artificial light radiation is generated using a device chosen from arc lamps such as xenon lamps and mercury lamps, fluorescent lamps, incandescent lamps such as halogens, light-emitting diodes (LEDs), organic light-emitting diodes (LEDs), and lasers. 13. Composition (B) comprising i) one or more compounds of formula (I) as defined in any one of claims 1 to 7; ii) one or more polyamino acids as defined in any one of claims 1, 9 or 10 and iii) one or more amines as defined in claim 11 14. Device with several compartments: - including: * either in a compartment the ingredient i) one or more compounds of formula (I) as defined in any one of claims 1 to 7, and in another compartment the ingredient ii) one or more polyamino acids as defined in a any of claims 1, 9 to 10, * or in a compartment the ingredients i) one or more compounds of formula (I) as defined in any one of claims 1 to 7, and ii) one or more polyamino acids as defined in any one of claims 1, 9 to 10, i) and ii) being together, and - in another compartment, an artificial light emitting device as defined in claim 12. 15. Cosmetic use i) of one or more compounds of formula (I) as defined in any one of claims 1 to 7, and ii) of one or more 43 polyamino acids as defined in any one of claims 1, 9 to 10, and of artificial or natural light radiation as defined in claim 1 or 12; in particular for the care and / or repair of the hair, preferably for the repair of the hair.