Patent Application
20230148252
The present invention relates to a process for treating keratin materials, especially human keratin fibers, comprising the application of a composition comprising i) at least one flavin derivative and ii) at least one polymerizable molecule, preferably a photopolymerizable molecule, and at least one step of exposing said materials to artificial or natural light radiation, in particular for caring for and/or repairing the keratin materials.
The hair is damaged and weakened by external atmospheric agents such as pollution and bad weather, and also by mechanical or chemical treatments, such as brushing, combing, dyeing, bleaching, permanent-waving, relaxing and repeated washing. The hair thus becomes damaged and may in the long run become dry, coarse, brittle, dull, split and/or soft or else sensitive to humidity, making the hair unmanageable, often with frizziness, and/or difficult to style in a humid environment, in particular in a very humid environment. The hair is then also sensitive to mechanical constraints such as being gripped with an elastic band, for example to make a ponytail, and retains the gripping mark even after the elastic band has been taken off.
To overcome these drawbacks, it is common practice to make use of hair compositions for conditioning the hair by giving it cosmetic properties and also good shaping.
However, the conditioning effect obtained via these hair treatments fades out rapidly over time, and in particular does not have satisfactory persistence with respect to shampoo washing.
Furthermore, these hair compositions have little or no effect on controlling the volume of keratin fibers and/or holding the hairstyle and/or managing the hair in a humid or even a very humid environment (humidity-resistant shape and volume control). They also have little or no effect on the sensitivity to mechanical constraints such as being gripped with an elastic band.
There is thus a real need to develop processes for treating keratin fibers that are capable of conserving or even improving the quality of the fiber such as the softness, disentangling, smoothness, manageability, volume and strength of the hair, for example by reducing the brittleness of the hair, and doing so in a persistent manner, or else by making the hair less sensitive to mechanical constraints such as gripping, or by allowing control of the volume and frizziness and/or shape of the keratin fibers and also of the hairstyle in a humid environment, in particular a very humid environment.
In addition, it is known that riboflavin can initiate photochemical reactions such as the crosslinking of polysaccharides to form hydrogels (see, for example, WO 2010/083039, J. Biomed. Mater. Res. B. Appl. Biomater., Kim, S.-H., Chu, C.-C., 91(1), 390-400 (2009). Other hydrogels have been prepared as riboflavin “delivery drug” [see, for example, Drug. Discovery Today, Piyush Gupta, Kavita Vermani and Sanjay Garg, Vol. 7, No. 10 (2002)]. The hydrogels tested with riboflavin or derivatives have not been used in the field of cosmetics.
WO2016/126121 discloses a composition for scalp and hair comprising a yeast extract, wherein the yeast extract may comprise vitamin B2 (riboflavin).
There is still a need to develop a process for treating keratin materials, in particular keratin fibers such as the hair, more particularly a process for treating keratin fibers in an efficient and long-lasting manner while at the same time limiting the perceived degradation of the hair, in particular in a way that is persistent with respect to successive shampoo washes and to control the shape of the humidity-resistant keratin fibers.
There is also a need to develop a process for treating keratin materials, in particular keratin fibers, especially human keratin fibers such as the hair, more particularly a keratin fiber treatment process that is efficient and, if possible, long-lasting while at the same time limiting the perceived degradation of the hair, especially the perception of dry, coarse, brittle, dull, split and/or soft hair or else hair that is sensitive to humidity often with frizziness, and/or that is difficult to style in a humid environment, in particular in a very humid environment, and especially by making the hair insensitive to mechanical constraints such as gripping with an elastic band so as, for example, to make a ponytail.
This (these) aim(s) are achieved by the process of the invention, i.e. a process for treating keratin materials, in particular keratin fibers, especially human keratin fibers such as the hair, comprising:
i) one or more flavin derivatives chosen from the compounds of formula (I) below:
and also the organic or mineral acid or base salts thereof, the optical isomers, geometrical isomers and tautomers thereof, and the solvates thereof such as hydrates; in which formula (I):
The invention also relates to a process for preparing a composition (B), comprising step a) of mixing i) one or more flavin derivatives chosen from the compounds of formula (I) as defined previously, ii) one or more polymerizable molecules as defined below and iii) optionally one or more amines and/or one or more alcohols different i) from the flavins of formula (I), and different ii) from the polymerizable molecules, preferably one or more amines chosen from amino acids; followed by a step b) of exposing said mixture to artificial or natural light radiation.
The invention also relates to a process for preparing a composition (B′), comprising step a) of mixing i) one or more flavin derivatives chosen from the compounds of formula (I) as defined previously, ii) one or more polymerizable molecules chosen from those of formula (II), (IIa), (IIb) or (IIc) as defined below and iii) optionally one or more amines and/or one or more alcohols different i) from the flavins of formula (I), and different ii) from the polymerizable molecules, preferably one or more amines chosen from amino acids; followed by a step b) of exposing said mixture to artificial or natural light radiation.
A subject of the invention is also composition (B) obtained via the process as described previously.
A subject of the invention is also composition (B′) obtained via the process as described previously.
A subject of the invention is also a process for treating keratin materials, in particular keratin fibers, especially human keratin fibers such as the hair, comprising a step of applying to said materials a composition (B) or (B′) obtained via the preparation process as described previously and optionally a step 2) of supplying energy to said materials, consisting in exposing said materials to at least one artificial or natural light radiation, the optional energy supply step 2) being performed simultaneously with the step of applying composition (B) or (B′) or successively to the step of applying composition (B) or (B′) to the keratin materials.
A subject of the invention is also a multi-compartment kit or device:
Another subject of the invention is the cosmetic use i) of one or more compounds of formula (I) as defined previously in the presence ii) of one or more polymerizable molecules and of at least one artificial or natural light radiation; in particular for caring for and/or repairing keratin materials, especially human keratin fibers such as the hair, preferably for repairing the hair.
The processes of the invention use either a composition (A), (B) or (B) containing at least one flavin derivative of formula (I) as defined previously, especially at least one riboflavin phosphate derivative (vitamin B2 derivative), optionally an amino acid such as arginine and at least one polymerizable and especially photocrosslinkable molecule, followed by a step of irradiating with light radiation, and make it possible to improve the cosmetic qualities of keratin fibers. The fibers appear repaired. Fibers treated via one of the processes of the invention after they have been marked or deformed by a mechanical constraint, such as during the gripping of the fibers with a clip, hair slides, or other elastic means such as an elastic band, for example with a ponytail, are improved relative to untreated fibers where the ponytail leaves a long-lasting imprint on the fibers. With one of the processes of the invention, the imprint disappears rapidly, or even immediately.
Other characteristics and advantages of the invention will emerge more clearly on reading the description and the examples that follow.
In the following text, unless indicated otherwise:
Compositions (A), (B) or (B′) of the invention comprise at least one compound of formula (I) as defined previously.
According to a particular embodiment of the invention, the compounds of formula (I) are such that R1, R2, R3 and R4, which may be identical or different, represent a hydrogen atom, (C1-C6)alkyl, (C1-C6)alkoxy or (di)(C1-C4)(alkyl)amino, in particular chosen from hydrogen and (C1-C4)alkyl. Preferably, R1 and R4 represent a hydrogen atom, and R2 and R3 represent a hydrogen atom or a (C1-C4)alkyl group such as methyl, preferably a (C1-C4)alkyl group such as methyl.
According to a particular embodiment of the invention, the compounds of formula (I) are such that R5 represents a (C1-C6)alkyl group such as methyl.
According to another preferred embodiment of the invention, the compounds of formula (I) are such that R5 represents a (C1-C6)alkyl group substituted with one or more identical or different groups chosen from i) hydroxyl, ii) R6—C(O)—O— with R6 representing a hydrogen atom or a (C1-C4)alkyl group such as methyl or n-propyl; iii) phosphoric (HO)2P(O)—O—, iv) —O—[(HO)P(O)—O]n-Suc-Het with Suc representing a monosaccharide such as ribose, and Het representing an optionally substituted heteroaryl group, in particular optionally substituted pyrimidyl-dione such as adenine, n is an integer equal to 1 or 2, preferably 2; in particular, Suc-Het represents a ribose group, preferably α-D-ribose, optionally substituted with an adenine group.
According to a preferred embodiment, the compounds of formula (I) are such that the radical Suc represents a divalent monosaccharide radical in which the heterocycle constituting it contains 4 or 5 carbon atoms, having the following formula:
Ra representing a (C1-C4) alkylene group such as methylene and Ra being linked to the rest of the molecule via at least one phosphate group, it being understood that the radical Ra is in position C5 if the sugar unit is in pyranose form or in position C4 if it is in furanose form;
represents the two substitution parts of the divalent monosaccharide.
According to a more particular embodiment, the compounds of formula (I) are such that R5 represents the following group:
with Ra, A, Het and m as defined previously;
representing the part that is linked to the rest of the molecule.
Preferably, Het represents a purine or pyrimidine nitrogenous 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 which is optionally substituted especially with one or more (di)(C1-C4)(alkyl)amino groups; preferentially, Het is a purine nitrogenous base such as adenine.
According to a more particular embodiment, the compounds of formula (I) are such that R5 represents a (C1-C6)alkyl group optionally substituted with one or more hydroxyl or phosphate groups such as pentyl substituted with one, two, three or four hydroxyl 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 NR9 with R9 representing a hydrogen atom or a (C1-C6)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 and 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 compounds 1 to 7 below:
and also the organic or mineral acid or base salts thereof, the optical isomers and tautomers thereof, and the solvates thereof such as hydrates, in particular the salt thereof with an alkali metal such as sodium.
According to a particular embodiment, compositions (A), (B) or (B′) comprise one or more compounds of formula (I) as defined previously, in an amount inclusively between 0.01% and 30% by weight relative to the total weight of composition (A), (B) or (B′), in particular between 0.05% and 20%, more particularly between 0.1% and 10%, preferentially between 1% and 5% by weight relative to the total weight of composition (A), (B) or (B′).
According to a particular embodiment of the invention, the polymerizable molecule(s) have a molecular weight of less than or equal to 500 g/mol, preferably a molecular weight inclusively between 26 and 400 g/mol.
Preferably, the polymerizable molecules are photo-polymerizable, i.e. they have the capacity of polymerizing under exposure to at least one natural and/or artificial light radiation.
Preferably, the polymerizable molecule(s) are chosen from those of formula (II) below:
and also the organic or mineral acid or base salts thereof, the optical isomers, geometrical isomers and tautomers thereof, and the solvates thereof such as hydrates; in which formula (II):
denoting the point of attachment between alk and Y2 in the case of formula (Z′) and
denoting the point of attachment between (Y2)p and alk in the case of formula (Z″).
According to a particular variant of the invention, Z denotes a radical R4. According to one embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical R4 and R1 represents a hydrogen atom or a (C1-C4)alkyl group. According to one embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical R4 and R1 represents a hydrogen atom. According to another particular embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical R4 and R1 represents a (C1-C4)alkyl group such as methyl.
According to another embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical R4 and R1 represents a (C1-C4)alkyl group substituted with a radical chosen from hydroxyl and —C(Y′1)—(Y′2—R′4, in particular —C(O)—O—R′4 with R′4 as defined previously; preferably R1 denotes a (C1-C4)alkyl group substituted with a carboxyl group such as carboxymethyl.
According to one embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical R4 and R2 represents a hydrogen atom, a (C1-C4)alkyl group optionally substituted with one or more radicals chosen from hydroxyl, (di)(C1-C4)(alkyl)amino, (C1-C4)alkoxy and carboxyl radicals, R2 preferably represents a hydrogen atom or a (C1-C4)alkyl group such as methyl, in particular a hydrogen atom.
According to one embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical R4 and R3 represents i) a hydrogen atom, ii) a (C1-C4)alkyl group optionally substituted with one or more radicals chosen from hydroxyl, (di)(C1-C4)(alkyl)amino, (C1-C4)alkoxy and carboxyl radicals; iii)
According to one embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical R4 and R3 represents i) a hydrogen atom.
According to another embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical R4 and R3 represents a (C1-C4)alkyl group optionally substituted with a radical chosen from hydroxyl and carboxyl.
According to another embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical R4 and R3 represents —C(O)—O—R′4 with R′4 as defined previously.
According to one embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical R4 and R4 and R′4, which may be identical or different, represent i) a hydrogen atom, or ii) a (C1-C4)alkyl group such as methyl, preferably a hydrogen atom.
According to another embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical R4, and R4 and R′4, which may be identical or different, represent a (C1-C16)alkyl group substituted with one or more radicals, which may be identical or different, chosen from the following radicals: amino (NH2), mono- or di(C1-C4)alkylamino such as dimethylamino, hydroxyl (OH), SO3H, carboxyl (CO2H), cyano, trifluoromethyl (CF3), (C1-C4)alkyloxycarbonyl, which is preferably monosubstituted; according to this embodiment, R4 and R′4, which may be identical or different, in particular represent a (C1-C6)alkyl group substituted with one or more radicals, which may be identical or different, chosen from the following radicals: amino (NH2), mono- or di(C1-C4)alkylamino such as dimethylamino, hydroxyl (OH), SO3H, carboxyl (CO2H), cyano, said radical preferably being monosubstituted, such as the 2-hydroxypropyl radical.
According to another embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical R4, and R4 and R′4, which may be identical or different, represent a (C1-C16)alkyl group interrupted with one or more heteroatoms, such as O, S and N(R5) with R5 as defined previously, and preferably R5 denoting H or Me; according to this embodiment, R4 and R′4, which may be identical or different, represent a (C1-C16)alkyl group interrupted with one or more non-adjacent oxygen atoms and especially a radical —(CH2CH2O)n—R in which n denotes an integer equal to 0 or 1 or 2 or 3 or 4 or 5 and R denotes a C1-C6 alkyl radical such as methyl or ethyl, or alternatively R4 and R′4 independently denote a 2-ethoxyethyl radical.
According to a particular variant of the invention, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical of formula (Z′).
Preferably, the polymerizable molecules of formula (II) are such that Z denotes a radical of formula (Z′) and (Z′) represents a group chosen from:
a) —(CH2)nX with X representing a group from among: hydroxyl, amino, (di)(C1-C4)alkylamino such as dimethylamino, sulfonic —SO3H, carboxyl or cyano and n representing an integer between 1 and 5 inclusive;
b) —(CH2CH2O)n—R and n is as defined above, R representing a hydrogen atom or a (C1-C4)alkyl group such as methyl;
c) —(CH2)n(CF3)m and n is equal to 1, 2 or 3 and m is an integer between 1 and 8 inclusive.
According to one embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical of formula (Z′), and Y1a and Y2a represent an oxygen atom.
According to one embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical of formula (Z′) and R1 represents a hydrogen atom or a (C1-C4)alkyl group such as methyl.
According to one embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical of formula (Z′) and R1 represents a hydrogen atom.
According to another embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical of formula (Z′) and R1 represents a (C1-C4)alkyl group substituted with a radical chosen from hydroxyl and —C(Y′1)—Y′2—R′4, in particular —C(O)—O—R′4 with R′4 as defined previously; preferably R1 denotes a (C1-C4)alkyl group substituted with a carboxyl group such as carboxymethyl.
According to one embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical of formula (Z′) and R2 represents a hydrogen atom or a (C1-C4)alkyl group optionally substituted with one or more radicals chosen from hydroxyl, (di)(C1-C4)(alkyl)amino, (C1-C4)alkoxy and carboxyl radicals; preferably, R2 represents a hydrogen atom.
According to one embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical of formula (Z′) and R3 represents i) a hydrogen atom, ii) a (C1-C4)alkyl group optionally substituted with one or more radicals chosen from hydroxyl, (di)(C1-C4)(alkyl)amino, (C1-C4)alkoxy and carboxyl radicals; iii) —C(O)—O—R′4.
According to one embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical of formula (Z′) and R3 represents i) a hydrogen atom. According to another embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical of formula (Z′) and R3 represents a (C1-C4)alkyl group optionally substituted with a radical chosen from hydroxyl and carboxyl.
According to another embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical of formula (Z′) and R3 represents —C(O)—O—R′4 with R′4 as defined previously.
According to one embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical of formula (Z′), and R4 and R′4, which may be identical or different, represent i) a hydrogen atom, or ii) a (C1-C4)alkyl group such as methyl, preferably a hydrogen atom.
According to another embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical of formula (Z′), and R4 and R′4, which may be identical or different, represent a (C1-C16)alkyl group substituted with one or more radicals, which may be identical or different, chosen from the following radicals: amino (NH2), mono- or di(C1-C4)alkylamino such as dimethylamino, hydroxyl (OH), SO3H, carboxyl (CO2H), cyano, trifluoromethyl (CF3), (C1-C4)alkyloxycarbonyl, which is preferably monosubstituted; according to this embodiment, R4 and R′4, which may be identical or different, in particular represent a (C1-C6)alkyl group substituted with one or more radicals, which may be identical or different, chosen from the following radicals: amino (NH2), mono- or di(C1-C4)alkylamino such as dimethylamino, hydroxyl (OH), SO3H, carboxyl (CO2H), cyano, said radical preferably being monosubstituted, such as the 2-hydroxypropyl radical.
According to another embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical of formula (Z′), and R4 and R′4, which may be identical or different, represent a (C1-C16)alkyl group interrupted with one or more heteroatoms, such as O, S and N(R5) with R5 as defined previously, and preferably R5 denoting H or Me; according to this embodiment, R4 and R′4, which may be identical or different, represent a (C1-C16)alkyl group interrupted with one or more non-adjacent oxygen atoms and especially a radical —(CH2CH2O)n—R in which n denotes an integer equal to 0 or 1 or 2 or 3 or 4 or 5 and R denotes a C1-C6 alkyl radical such as methyl or ethyl, or alternatively R4 and R′4 independently denote a 2-ethoxyethyl radical.
According to another embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical of formula (Z′) and alk denotes a (C1-C16)alkylene radical (divalent radical) optionally interrupted with one or more oxygen or sulfur atoms or with one or more NH groups, said divalent radical alk preferably denoting a (C1-C16)alkylene radical (divalent radical) optionally interrupted with one or more oxygen atoms, such as a radical —(CH2—CH2—O)q with q=1 to 8.
According to another embodiment, the polymerizable molecule(s) are of formula (II) in which Z denotes a radical of formula (Z′) and alk denotes a (C1-C16)alkylene and preferably (C1-C6)alkylene radical (divalent radical) such as a C5 alkyl radical or a C4 alkyl radical or a C3 alkyl radical, said radical alk being optionally substituted with one or more hydroxyl radical and/or one or more radicals of formula (Z″) as defined previously, preferably optionally substituted with a hydroxyl radical and substituted with one or two radicals of formula (Z″) as defined previously. According to this embodiment, when alk is substituted with one or two radicals of formula (Z″):
More particularly, the polymerizable molecule(s) are chosen from those of formula (IIa) below:
and also the organic or mineral acid or base salts thereof, the optical isomers, geometrical isomers and tautomers thereof, and the solvates thereof such as hydrates; in which formula (IIa) R1, R3 and R4 are as defined previously.
In another particular variant, the polymerizable molecule(s) are chosen from those of formula (IIb) below:
and also the organic or mineral acid or base salts thereof, the optical isomers, geometrical isomers and tautomers thereof, and the solvates thereof such as hydrates; in which formula (IIb) R1 and R2 are as defined previously, in particular chosen from hydrogen or (C1-C4)alkyl such as methyl, preferably hydrogen.
According to another variant, the polymerizable molecules are chosen from those of formula (IIc) below:
and also the organic or mineral acid or base salts thereof, the optical isomers, geometrical isomers and tautomers thereof, and the solvates thereof such as hydrates;
in which formula (IIc) R1, R2, R3, Y1, Y2, alk, Y2a, Y1a, R1a, R2a and R3a are as defined previously, in particular such that R1═R1a and R2═R2a and R3═R3a and Y1═Y1a and Y2═Y2a. In particular, the polymerizable molecules are chosen from those of formula (IIc) for which:
According to this variant, the polymerizable molecules are chosen from compounds (B′) to (d) below:
Preferably, the polymerizable molecule(s) are chosen from ((C1-C4)alkyl)acrylic acid such as methacrylic acid, acrylic acid and itaconic acid, in particular itaconic acid and also the organic or mineral base salts thereof and the solvates thereof such as hydrates.
According to a particular embodiment, compositions (A), (B) or (B′) comprise one or more polymerizable molecules as defined previously, in an amount inclusively between 0.01% and 50% by weight relative to the total weight of compositions (A), (B) or (B′), in particular between 0.1% and 40%, more particularly between 1% and 30%, preferentially between 2% and 20%, more preferentially between 5% and 10% by weight relative to the total weight of compositions (A), (B) or (B′).
iii) The Amines
Compositions (A), (B) or (B′) optionally comprise one or more amines.
According to one variant, compositions (A), (B) or (B′) comprise one or more amines.
According to the invention, the term “amines” means any organic molecule comprising at least one primary, secondary or tertiary amine group, other than i) the riboflavins of formula (I), and other than ii) the polymerizable molecules. The amines may be aromatic or nonaromatic, saturated or unsaturated, oligomeric or polymeric, and natural or synthetic.
According to a preferred embodiment, the amine(s) of the invention are present in compositions (A), (B) or (B′) in an amount of between 0.01% and 15% by weight relative to the total weight of the composition which comprises same, more particularly between 0.05% and 5%, more preferentially between 0.1% and 3% by weight relative to the total weight of the composition which comprises same.
According to a particular embodiment of the invention, compositions (A), (B) or (B′) of the invention comprise at least one amino acid, preferably a natural amino acid.
Preferably, the amino acid(s) are chosen from the compounds of formula (III) below:
and also the organic or mineral acid or base salts thereof, the optical isomers, geometrical isomers and tautomers thereof, and the solvates thereof such as hydrates;
In particular, the amino acid(s) are chosen from alanine, arginine and proline, preferably L-alanine, L-arginine and L-proline, in particular L-arginine or L-proline, more preferentially L-arginine.
According to a preferred embodiment, the amino acid(s) of formula (III) of the invention are present in composition (A) or in composition (B) in an amount of between 0.01% and 15% by weight relative to the total weight of the composition which comprises same, more particularly between 0.05% and 5%, more preferentially between 0.1% and 3% by weight relative to the total weight of the composition which comprises same.
According to another particular embodiment of the invention, 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—NReRf
and also the organic or mineral acid or base salts thereof, the optical isomers thereof, and the solvates thereof such as hydrates;
in which formula (IV):
Preferably, the compounds of formula (IV) are a benzylamine.
According to a preferred embodiment, the amine(s) of formula (IV) are present in composition (A) or in composition (B) in an amount of between 0.01% and 20% by weight relative to the total weight of the composition which comprises same, more particularly between 0.05% and 10%, more preferentially between 0.05% and 5% by weight relative to the total weight of the composition which comprises same.
According to yet another particular embodiment of the invention, composition (A), (B) or (B′) comprises at least one amino monosaccharide or at least one amino polysaccharide.
More preferentially, the monosaccharide(s) bearing amine group(s) a) of the invention are hexosamines of formula (V) and also the salts thereof with an organic or mineral acid such as hydrochloric acid, and also the α or β anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates:
in which formula (V):
in which formula (V′) Ra, Rb, Rd, Re and Rf are as defined for (V) above.
According to a preferred embodiment, the amino monosaccharide(s) of the invention are present in compositions (A), (B) or (B) in an amount of between 0.01% and 20% by weight relative to the total weight of the composition which comprises same, more particularly between 0.05% and 10%, more preferentially between 0.1% and 5% by weight relative to the total weight of the composition which comprises same.
According to yet another particular embodiment of the invention, composition (A), (B) or (B) comprises at least one polysaccharide bearing an amino group, and also the organic or mineral acid salts thereof, the α or β anomers thereof, the optical isomers thereof of L or D configuration and the solvates thereof such as hydrates.
According to a preferred embodiment of the invention, the amino polysaccharide(s) have an average molecular weight MW of less than or equal to 400 kDa, particularly less than 200 kDa.
According to a particular embodiment of the invention, the amino polysaccharide(s) are chosen from those bearing C5-C7 saccharide units and also the organic or mineral acid salts thereof, the α or β anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates.
According to one particular embodiment, the saccharide units of the amino polysaccharide(s) are linked together between the C1 carbon atoms of one saccharide unit and the C4 carbon atoms of the other saccharide unit, denoted (1→4), such as the amino polysaccharides of formula (VI) below, and also the organic or mineral acid salts thereof, the α or β anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates:
in which formula (VI):
More particularly, the amino polysaccharide(s) of the invention are of formula (VI1) below, and also the organic or mineral acid salts thereof, the α or β anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates:
in which formula (VW:
Preferentially, the amino polysaccharide(s) of the invention are chosen from chitin and chitosan and derivatives thereof, preferably chitosan.
More particularly, the amino polysaccharide(s) of the invention are chosen from those of formula (VI2) below, and also the organic or mineral acid salts thereof, and the solvates thereof such as hydrates:
in which formula (VI2):
More particularly, the amino polysaccharide(s) of the invention are chosen from the chitosans of formula (VI3) below, and also the organic or mineral acid salts thereof, and the solvates thereof such as hydrates:
in which formula (VI3):
For example, when m=0.7, p=0.3 this means that 70% of the amine groups are free (unsubstituted) and 30% of the amino groups are N-alkyl(C1-C4)carbonyl groups, in particular N-acetyl groups, corresponding to the chitosan of formula:
with n as defined above.
According to another form of the invention, the amino polysaccharide(s) of the invention denote a single amino polysaccharide, in particular a chitosan or the organic or mineral acid salts thereof or more particularly the organic acid salts thereof such as the lactic acid salt thereof, the α or β anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates.
According to a preferred embodiment, the amino polysaccharide(s) of the invention in particular of formula (VI), (VI1), (VI2) or (V3) as defined previously are present in composition (A) or (B) in an amount of between 0.01% and 20% by weight relative to the total weight of the composition which comprises same, more particularly between 0.05% and 10%, more preferentially between 0.1% and 5% by weight relative to the total weight of the composition which comprises same.
According to a particular embodiment, composition (A), (B) or (B′) comprises at least one amino acid of formula (III) and/or at least one amino a saccharide of formula (V) or (V) and/or at least one amino polysaccharide, these compounds being present in compositions (A), (B) or (B′) in amount(s) of between 0.01% and 20% by weight relative to the total weight of the composition which comprises same, more particularly between 0.05% and 10%, more preferentially between 0.05% and 5% by weight relative to the total weight of the composition which comprises same.
Alcohols
Compositions (A), (B) or (B′) optionally comprise one or more alcohols.
According to another variant, compositions (A), (B) or (B′) comprise one or more alcohols.
According to the invention, the term “alcohol” means any organic molecule comprising at least one hydroxyl group, other than i) the riboflavins of formula (I), and other than ii) the polymerizable molecules. The alcohols may be aromatic or nonaromatic, saturated or unsaturated, oligomeric or polymeric, and natural or synthetic.
According to a particular embodiment of the invention, composition (A), (B) or (B′) of the invention comprises at least one alcohol comprising an optionally substituted (hetero)aryl group, in particular of formula (IV′):
CYC—(X)q-(ALK)p—OH(IV′)
and also the organic or mineral acid or base salts thereof, the optical isomers thereof, and the solvates thereof such as hydrates;
in which formula (IV′):
Preferably, the compounds of formula (IV) are chosen from benzyl alcohol, phenoxyethanol and N,N-dimethylaminobenzyl alcohol.
According to another preferred embodiment of the invention, the alcohols are chosen from terpenes, more preferentially chosen from menthol, isoborneol and neomenthol.
According to another particular embodiment, the alcohols are chosen from linear or branched, saturated or unsaturated (C1-C6) alkanols, such as isopropanol.
According to another particular embodiment of the invention, 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
and also the organic or mineral acid or base salts thereof, the optical isomers thereof, and the solvates thereof such as hydrates;
in which formula (IV):
According to a preferred embodiment, the alcohol(s), in particular the alcohol(s) of formula (IV) or (IV), are present in compositions (A), (B) or (B′) in an amount of between 0.01% and 20% by weight relative to the total weight of the composition which comprises same, more particularly between 0.05% and 10%, more preferentially between 0.05% and 5% by weight relative to the total weight of the composition which comprises same.
According to a preferred embodiment of the invention, compositions (A), (B) or (B) comprise one or more amines, in particular amino acids, and one or more alcohols as defined previously, in an amount inclusively between 0.01% and 30% by weight relative to the total weight of compositions (A), (B) or (B′), in particular between 0.05% and 20%, more particularly between 0.1% and 10%, preferentially between 1% and 5% by weight relative to the total weight of compositions (A), (B) or (B′).
According to the process of the invention, step 2) comprises the exposure of keratin materials to at least one artificial and/or natural light radiation which may be continuous or non-continuous, before, during or after application of compositions (A), (B) or (B) as defined previously to said materials.
According to the process of the invention, step 2) in particular comprises the exposure of keratin materials to at least one artificial and/or natural light radiation which may be continuous or non-continuous, before, during or after application of compositions (A), (B) or (B) as defined previously to said materials.
For the purposes of the invention, the term “artificial light radiation” means light radiation other than natural daylight (generated by the sun). In other words, natural daylight (generated by the sun) is not artificial light radiation.
The term “natural radiation” means radiation whose sole light source is that of the day generated by the sun.
Preferably, the exposure of the keratin fibers to artificial light radiation is performed at a wavelength of between 360 and 600 nm, preferably between 375 and 550 nm, more preferentially between 400 and 480 nm.
Preferably, the artificial light radiation has an amount of energy per unit area of greater than or equal to 1 J/cm2, more preferentially strictly greater than 1 J/cm2, even more preferentially between 1.001 and 100 J/cm2, better still between 2 and 50 J/cm2, particularly preferably between 3 and 10 J/cm2.
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 halogen lamps, light-emitting diodes (LED), organic light-emitting diodes (OLED) and lasers.
Mention may be made, for example, of goLITE BLU from the company Philips, the lamp Energylight HF 3319/01 from the company Philips, the lamps Dayvia White and Messa from the company Solvital, the lamp Lumino Plus from the company Lanaform, the lamp Medibeam from the company Medibeam, the lamp M-LED 01 from the company Meimed, the lamp Lifemax Light Pod from the company Lifemax, the lamp Lite-Pad from the company Reicorp, the lamps Omnilux Clear-U and New-U from the company Omnilux, the 1000 W xenon arc lamp from the company Lot-Oriel and the lamp Camag Box 3 (4×8 W) from the company Camag.
Preferably, the duration of exposure of the keratin materials to artificial or natural light radiation is greater than or equal to 5 seconds, more preferentially between 10 seconds and 60 minutes, even more preferentially between 15 seconds and 50 minutes, and better still between 20 seconds and 40 minutes.
According to a first variant of the invention, the invention relates to a process (1) for treating keratin materials, in particular keratin fibers, especially human keratin fibers such as the hair, comprising:
According to another variant of the invention, the invention relates to a process (2) for treating keratin materials, in particular keratin fibers, especially human keratin fibers such as the hair, comprising:
1) a step of applying a composition (B) or (B) as defined previously; and
2) a step of supplying energy to said keratin materials, which consists in exposing said materials to at least one artificial or natural light radiation,
steps 1) and 2) possibly being performed simultaneously with the application, or sequentially, preferably simultaneously with the application or else sequentially 1) and then 2).
Preferably, the process of the invention is process (1).
According to a particular embodiment of the invention, process (1) for treating keratin materials of the invention involves at the same time (simultaneously) steps 1) and 2).
According to one variant, at the same time as the application of composition (A) to the keratin materials, said materials are exposed to at least one artificial and/or natural light radiation.
According to another variant of the invention according to process (2), composition (A) is exposed to at least one artificial and/or natural light radiation to give composition (B), said composition (B) then being applied to the keratin materials.
According to a particular embodiment of the invention, when steps 1) and 2) of the process are performed simultaneously, the duration of exposure of the keratin materials to at least one artificial and/or natural light radiation is between 5 seconds and 3 hours, preferably between 1 minute and 1 hour, such as 15 minutes; optionally followed by a step of rinsing said keratin fibers.
According to a preferred embodiment of the invention, when step 2) is performed after step 1), the duration of exposure of the keratin materials to artificial or natural light radiation is between 5 seconds and 3 hours, preferably between 1 minute and 1 hour, such as 15 minutes; optionally, a step of leaving composition (A) on said keratin fibers for a time of between 5 seconds and 3 hours, preferably between 1 minute and 1 hour, such as 15 minutes, is performed between step 1) and step 2); optionally, a step of rinsing said keratin fibers is performed after step 2).
According to another preferred embodiment of the invention, when step 2) is performed after step 1), the duration of exposure of the keratin materials to artificial or natural light radiation is between 5 seconds and 3 hours, preferably between 1 minute and 1 hour, such as 15 minutes; optionally, a step of leaving composition (A), (B) or (B) on said keratin fibers for a time of between 5 seconds and 3 hours, preferably between 1 minute and 1 hour, such as 15 minutes, is performed between step 1) and step 2); a step of rinsing said keratin fibers is performed after step 1).
Compositions (A), (B) or (B) of the invention may be applied to dry or wet keratin materials, preferably to dry or wet hair, preferably to dry hair.
The bath ratio of the applied compositions may range from 0.1 to 10, more particularly from 0.2 to 5 and preferably between 0.5 and 3. The term “bath ratio” means the ratio between the total weight of the applied composition and the total weight of keratin materials to be treated.
In particular, the step of applying composition (A), (B) or (B) to the keratin materials may be followed by a leave-on time. The leave-on time, i.e. the time of contact of composition (A), (B) or (B′) with the keratin materials, is preferably at least 5 minutes, preferably between 10 and 60 minutes and preferably between 15 and 45 minutes.
Rinsing of the hair may optionally be envisaged after applying composition (A), (B) or (B) and optionally the leave-on time.
The hair may then optionally be wrung dry, preferably wrung dry.
Process for Preparing a Composition (B′)
According to a preferred embodiment of the invention, the process for preparing composition (B) comprises step a) of mixing i) one or more flavin derivatives chosen from the compounds of formula (I) as defined previously with ii) one or more polymerizable molecules chosen from those of formula (II), (IIa), (IIb) or (IIc) as defined previously and with iii) one or more amines and/or one or more alcohols other than the riboflavins of formula (I) and other than the polymerizable molecules of formula (II), (IIa), (IIb) or (IIc), preferably one or more amines chosen from amino acids; followed by a step b) of exposing said mixture to at least one artificial and/or natural light radiation, in particular for at least 10 minutes.
More particularly, the process for preparing composition (B′) comprises step a) of mixing i) one or more flavin derivatives chosen from the compounds of formula (I) as defined previously with ii) one or more polymerizable molecules chosen from those of formula (II), (IIa), (IIb) or (IIc) as defined previously and with iii) one or more amino acids preferably of formula (III) as defined previously; followed by a step b) of exposing said mixture to at least one artificial and/or natural light radiation, in particular radiation, for at least 2 minutes, preferably for between 2 minutes and up to 10 hours, more preferentially between 15 minutes and 5 hours, such as 3 hours.
A subject of the invention is also composition (B′) obtained via the process as described previously.
The process of the invention is preferably performed on keratin fibers, especially human keratin fibers, such as the hair.
According to one variant, the process of the invention is performed on keratin fibers, especially human keratin fibers, such as the hair. According to a particular variant of the invention, the process is performed on damaged, bleached or sensitized keratin fibers.
According to a particular form of the invention, the process of the invention is a process for treating keratin materials, in particular keratin fibers, especially human keratin fibers such as the hair, comprising:
According to another variant, the process is performed on “natural” keratin fibers, i.e. fibers that have not undergone any chemical treatment such as dyeing, bleaching or permanent-waving.
Compositions (A), (B) and (B′)
The Compositions
The composition(s) of the invention are cosmetic, i.e. they contain a physiologically acceptable medium, that is to say a medium that is compatible with human keratin materials such as the skin (of the body, face, around the eyes or the scalp), the hair, the eyelashes, the eyebrows, bodily hair, the nails or the lips.
The physiologically acceptable medium of the composition(s) used in the process according to the invention is advantageously an aqueous medium. It may be constituted, for example, of water or of a mixture of water and of at least one cosmetically acceptable organic solvent. Examples of organic solvents that may be mentioned include C2-C4 lower alcohols, such as ethanol and isopropanol; polyols, especially those containing from 2 to 6 carbon atoms, for instance glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol or diethylene glycol; polyol ethers, for instance 2-butoxyethanol, propylene glycol monomethyl ether and diethylene glycol monomethyl ether or monoethyl ether; and mixtures thereof.
The cosmetic compositions of the invention are preferably water-based and then comprise water at a concentration ranging from 10% to 99.5%, better still from 30% to 95% and even better still from 50% to 95% by weight relative to the total weight of the composition, and even more preferentially from 60% to 90% 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 provitamins other than the compounds of formula (I) including panthenol, fillers, dyestuffs, nacreous agents, opacifiers, sequestrants, film-forming polymers, cationic, anionic or neutral polymers, associative polymers, plasticizers, silicones, thickeners, oils, antifoams, moisturizers, emollients, penetrants, fragrances and preserving agents; preferably one or more nonionic, anionic, cationic or amphoteric surfactants, cationic, anionic or neutral polymers, or associative polymers.
Depending on their nature and the purpose of the composition, the usual cosmetic ingredients may be present in usual amounts, which can be readily determined by those skilled in the art and which may be, for each ingredient, between 0.01% and 80% by weight. Those skilled in the art will take care to select the ingredients included in the composition, and also the amounts thereof, so that they do not harm the properties of the compositions of the present invention.
These compositions may be packaged in pump-action bottles or in aerosol containers, so as to apply the composition in vaporized (lacquer) form or in the form of a mousse. Such packaging forms are indicated, for example, when it is desired to obtain a spray or a mousse, for treating the hair. In these cases, the composition preferably comprises at least one propellant.
pH of the Compositions:
The pH of compositions (A), (B) or (B) is preferably between 3 and 10, more particularly in the region of neutrality between 6 and 8, such as 7.
The pH values may be adjusted with an organic or mineral acid, or with an alkaline agent chosen from mineral or organic or hybrid alkaline agents or mixtures thereof.
The term “organic acid” means an acid, i.e. a compound that is capable of releasing a cation or proton H+ or H3O+ in aqueous medium, which comprises at least one optionally unsaturated, linear or branched C1-C20 hydrocarbon-based chain, a (hetero)cycloalkyl or (hetero)aryl group and at least one acidic chemical function chosen in particular from carboxyl C(O)OH, sulfonic SO3H, sulfinic SO2H, phosphonic PO3H2 and phosphinic PO2H2.
More particularly, the acids used are chosen from hydrochloric acid HCl, hydrobromic acid HBr, sulfuric acid H2SO4, alkylsulfonic acids: (C1-C6)Alk-S(O)2OH such as methylsulfonic acid and ethylsulfonic acid; arylsulfonic acids: Ar—S(O)2OH such as benzenesulfonic acid and toluenesulfonic acid; (C1-C6)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 carboxylic acid(s) of formula (D) below:
in which formula (D) or a salt thereof:
A represents a saturated or unsaturated, cyclic or non-cyclic, and aromatic or non-aromatic hydrocarbon-based group, which is monovalent when t is 0 or polyvalent when t is greater than or equal to 1, comprising from 1 to 50 carbon atoms, which is optionally interrupted with one or more heteroatoms and/or optionally substituted, especially with one or more hydroxyl groups; preferably, A represents a monovalent (C1-C6)alkyl group or a polyvalent (C1-C6)alkylene group optionally substituted with one or more hydroxyl groups.
Particularly, the carboxylic acid(s) of formula (D) as defined previously, and preferably the acid(s) used, are an alpha-hydroxy acid such as lactic acids, glycolic acids, tartaric acids or citric acids.
The mineral alkaline agent(s) are preferably chosen from aqueous ammonia, alkaline carbonates or bicarbonates such as sodium or potassium carbonates and sodium or potassium bicarbonates, sodium hydroxide or potassium hydroxide, or mixtures thereof.
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 preferentially chosen from organic amines with a pKb at 25° C. of less than 12, preferably of less than 10 and even more advantageously of less than 6. It should be noted that it is the pKb corresponding to the function of highest basicity.
Hybrid compounds that may be mentioned include the salts of the amines mentioned previously with acids such as carbonic acid or hydrochloric acid. The organic alkaline agent(s) are chosen, for example, from alkanolamines, oxyethylenated and/or oxypropylenated ethylenediamines, amino acids and the compounds of formula (E) below:
in which formula (E):
Preferably, the alkanolamine is ethanolamine (or monoethanolamine).
In one variant of the invention, the composition comprises, as alkaline agent, one or more alkanolamines (preferably ethanolamine) and aqueous ammonia. In this variant, the alkanolamine(s) are present in a predominant amount relative to the aqueous ammonia.
The examples that follow serve to illustrate the invention without, however, being limiting in nature.
The process according to the invention makes it possible to obtain polymeric compounds which may be generated in keratin fibers or else externally to keratin fibers and then applied to said fibers.
Preparation of a Composition (B) or (B′) Intended to be Applied to Keratin Fibers:
An aqueous composition constituted of sodium riboflavin 5′-monophosphate hydrate (3 g %), L-arginine (3 g %), itaconic acid (38 g %) and water (pH adjusted to 7 with NaOH) was irradiated with a 1000 W xenon arc lamp for 3 hours to create a polymer composition (B), which was then applied to the fiber.
The following compositions were prepared according to the following table:
2.7 g of locks of 20 cm SA20 bleached hair, which were washed and dried beforehand, were used. 1.5 g of each formula were applied for each gram of dry hair. The samples were left on for 15 minutes, wrapped in a thin transparent plastic film. The film was removed and the hair was irradiated using a 1000 W xenon arc lamp for 15 minutes, and then rinsed with excess water at 37° C., combed and dried under a hood at 60° C. for 10 minutes. The placebo samples were prepared in an identical manner, except that the sample was covered with aluminum foil instead of transparent film (to protect it from irradiation). After drying, the samples were combed (comb passed through five times) and then left suspended vertically.
Effect of a Ponytail
The more the hair is damaged, the more the folding of the sample remains marked on the hair after the stress has been removed.
The locks were folded in two (the root toward the end of the hair) and fixed using an elastic band so as to make a loop of about 3 cm, i.e. the length of the loop is 3 cm or, in other words, the elastic band is 3 cm from the bottom of the loop. The looped locks were suspended with the loop at the bottom in a glove box at 80% RH and 26° C. for 2 hours. The locks were removed from the glove box, the elastic band was removed and the locks were suspended vertically. The fold angle was measured according to the reporter's principle (see
Results
Angle reduction=final angle−initial angle
The greater the angle reduction, the more the fold imprint disappears and the more longitudinal the lock.
After removing the elastic band, the locks numbered 14, 16 and 19 (present invention) show a better return longitudinal shape, i.e. the fold imprint is no longer visible on these locks. This is not the case for the other comparative locks (1 to 13 and 15, 17 and 18). In addition, it is seen that the damaged locks treated via the process of the invention are perceived as being identical to a natural lock, indicating that the process of the invention has repaired the damaged hair.
Comparative Study (Vs. WO2016/126121)
The use of the same yeast (Saccharomyces cerevisiae) as described in WO2016/126121 is not possible since the details of the supplier are not given neither any procedure to prepare the yeast nor the extraction procedure of the riboflavin. After a literature search it was concluded that the concentration of riboflavin in S. cerevisiae is between 0.8-1.5 μM. Thus the higher concentration of 1.5 μM has been used to do the comparative study. Therefore, a composition comprising 20% by weight of S. cerevisiae comprises an equivalent quantity of riboflavin of 1.13 g×10−4% by weight. A particular reference for the cytosolic concentration of riboflavin in S. cerevisiae is Biosynthesis of Vitamin B2 (Riboflavin), Annual Review of Nutrition, Vol. 20:153-167 (Volume publication date July 2000)-https://doi.org/10.1146/annurev.nutr.20.1.153
In this study, pentaerythritol tetraacrylate has been used as a polymerizable molecule:
The following formulations were prepared. The ingredients were mixed, stirred for one hour in an closed amber vial before use.
1Sigma-Aldrich - Ref. R7649
2Sigma-Aldrich - Ref. 408263
3Sigma-Aldrich - Ref. U4884
4BASF- Ref. Uvinul 40
5Sigma-Aldrich - Ref. X-100
The hair swatches (2.7 g, 27 cm length) were placed on a piece of aluminium foil. 5.4 g of each formulation was applied onto each hair swatch. The swatches were covered with a transparent plastic film to reduce evaporation. Examples 1, 3, and 5 were exposed to natural light for 60 minutes. After 30 of the 60 minutes the swatches were turned over to ensure each side of the swatches was exposed to at least 30 minutes of natural light. The irradiance of natural light was measured at 64 microW/cm2 using a Thor PM100D Optical Power Meter.
Examples 2, 4 and 6 were irradiated with a home-made array of LED lights emitting light at 450 nm for 60 minutes. The array of LEDs were positioned 5 cm above the swatch and the irradiance measured at 26 mW/cm2). After 30 of the 60 minutes the swatches were turned over to ensure each side of the swatches was irradiated to at least 30 minutes.
After exposure to the light all the swatches were suspended vertically, covered with a towel and left to dry.
The swatches were subjected to 5 repeat washes. Washing consisted of placing the swatch in a bath containing 100 mL of 3% sodium lauryl ether sulfate (SLES) for 1 minute then rinsing for 10 seconds under tap water. The process is repeated 4 times using fresh SLES solution each time. At the end of the fifth wash and rinse the swatches were dried in a professional helmet hairdryer at 60° C.
The swatches were suspended vertically and combed 30 times with a fine toothed comb at a speed of 30 cm/sec. The amount of broken hair was collected and weighed. The lower the weight of hair collected the better the formulation is at reducing the breakage of hair i.e. repairing the hair.
The results show that hair treated according to Examples 1 and 2 with 1% riboflavin and pentaerythritol tetraacrylate have been repaired since there is less hair breakage during the repeated combing. Example 2 using the LED array gave better results than natural light.
| Number | Date | Country | Kind |
|---|---|---|---|
| 1762637 | Dec 2017 | FR | national |
This is a national stage application of PCT/EP2018/085886, filed internationally on Dec. 19, 2018, which claims priority to French Application No. 1762637, filed on Dec. 20, 2017, both of which are incorporated by reference herein in their entirety.
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/EP2018/085886 | 12/19/2018 | WO |
