Process for treating keratin materials using a flavin derivative, a polymerizable molecule and light radiation

A method for treating keratin materials, wherein the method comprises:

• 1) applying to the keratin materials a composition (A) or a composition (B), wherein the composition (A) comprises i) at least one flavin derivative and ii) at least one polymerizable molecule, and the composition (B) is obtained by exposing the composition (A) to at least one artificial or natural light radiation;
• and
• 2) supplying energy to the keratin materials by exposing the keratin materials to at least one artificial or natural light radiation;
• wherein the at least one flavin derivative is chosen from compounds of formula (I) below:
• organic or mineral acid or base salts thereof, optical isomers thereof, geometrical isomers thereof, tautomers thereof, or solvates thereof;
• wherein in formula (I):
• R1, R2, R3 and R4, which may be identical or different, are chosen from a hydrogen atom, a halogen atom, or a group chosen from hydroxyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkylthio, (di)(C1-C6)(alkyl)amino, or nitro(so);
• R5 is chosen from a hydrogen atom or a (C1-C8)alkyl group optionally substituted with a group chosen from i) hydroxyl, ii) R6—C(Y″)—O—, wherein R6 is chosen from a hydrogen atom, a (C1-C4)alkyl group, or an aryl(C1-C4)alkyl group, and Y″ is chosen from an oxygen atom, a sulfur atom, or N(R7), wherein R7 is chosen from a hydrogen atom or a (C1-C4)alkyl group, iii) phosphoric (HO)2P(O)—O—, iv) —O—[(HO)P(O)—O]n-Suc-Het, wherein Suc is chosen from a divalent sugar group, and Het is chosen from a heteroaryl group, and n is an integer equal to 0, 1 or 2;
• X is chosen from a nitrogen atom or a methylene group C(R8), wherein R8 is chosen from a hydrogen atom or a (C1-C4)alkyl group;
• X′ is chosen from an oxygen atom or a group NR9, wherein R9 is chosen from a hydrogen atom or a (C1-C6)alkyl group;
• and
• Y and Y′, which may be identical or different, are chosen from an oxygen atom, a sulfur atom, or a group NR10, wherein R10 is chosen from a hydrogen atom or a (C1-C6)alkyl group;
• wherein steps 1) and 2) are performed simultaneously or step 2) is performed subsequently after step 1);
• and
• wherein the at least one polymerizable molecule comprises at least one unsaturated group.

A method for preparing a composition (B′), wherein the method comprises:

• mixing the following ingredients to obtain a mixture:
• i) at least one compound of formula (I),
• ii) at least one polymerizable molecule chosen from compounds of formula (II), (IIa), (IIb) or (IIc) below,
• and
• iii) optionally, at least one amine and/or at least one alcohol other than i) the compounds of formula (I), and other than ii) the at least one polymerizable molecule;
• and
• exposing the mixture to an artificial or natural light radiation for at least 2 minutes;
• wherein in formula (I):
• R1, R2, R3 and R4, which may be identical or different, are chosen from a hydrogen atom, a halogen atom, or a group chosen from hydroxyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkylthio, (di)(C1-C6)(alkyl)amino, nitro(so);
• R5 is chosen from a hydrogen atom or a (C1-C8)alkyl group optionally substituted with a group chosen from i) hydroxyl, ii) R6—C(Y″)—O—, wherein R6 is chosen from a hydrogen atom, a (C1-C4)alkyl group, or an aryl(C1-C4)alkyl group, and Y″ is chosen from an oxygen atom, a sulfur atom, or N(R7), wherein R7 is chosen from a hydrogen atom or a (C1-C4)alkyl group, iii) phosphoric (HO)2P(O)—O—, iv) —O—[(HO)P(O)—O]n-Suc-Het, wherein Suc is chosen from a divalent sugar group, and Het is chosen from a heteroaryl group, and n is an integer equal to 0, 1, or 2;
• X is chosen from a nitrogen atom or a methylene group C(R8), wherein R8 is chosen from a hydrogen atom or a (C1-C4)alkyl group;
• X′ is chosen from an oxygen atom or a group NR9, wherein R9 is chosen from a hydrogen atom or a (C1-C6)alkyl group;
• and
• Y and Y′, which may be identical or different, are chosen from an oxygen atom, a sulfur atom, or a group NR10, wherein R10 is chosen from a hydrogen atom or a (C1-C6)alkyl group;
• wherein in formulae (II), (IIa), (IIb) and (IIc):
• R1 and R2, which may be identical or different, are chosen from a hydrogen atom, a (C1-C8)alkyl group, or a (C2-C8)alkenyl group, wherein the (C1-C8)alkyl and the (C2-C8)alkenyl groups are:
• optionally interrupted with at least one heteroatom chosen from O, S, or N(R5), wherein R5 is chosen from a hydrogen atom or a (C1-C4)alkyl group, and/or
• optionally substituted with at least one radical chosen from the following radicals:
• hydroxyl, (di)(C1-C4)(alkyl)amino, (C1-C4)alkoxy, or —C(Y′1)—Y′2—R′4;
• R3 is chosen from a hydrogen atom, a (C1-C8)alkyl group, a (C2-C8)alkenyl group, or a —C(Y′1)—Y′2—R′4 group;
• Y1, Y2, Y′1 and Y′2, which may be identical or different, are chosen from an oxygen atom, a sulfur atom, or N(R5), wherein R5 is chosen from a hydrogen atom or a (C1-C4)alkyl group;
• and
• R4 and R′4, which may be identical or different, are chosen from a hydrogen atom or a (C1-C16)alkyl group optionally substituted with at least one radicals, which may be identical or different, chosen from the following radicals:
• a) amino (NH2), or mono- or di(C1-C4)alkylamino, b) hydroxyl (OH), c) SO3H, d) carboxyl (CO2H), e) cyano, f) (poly)(halo)(C1-C4)alkyl, g) (C1-C4)alkoxycarbonyl;
• wherein the alkyl radical is optionally interrupted with a heteroatom;
• Z is a radical R4 or a radical (Z′) of formula:
• wherein in formula (Z′):
• Y1a, Y2a, R1a, R2a and R3a have, respectively and independently, the same meanings as that of Y1, Y2, R1, R2 and R3;
• alk is a divalent (C1-C16)alkylene radical optionally interrupted with an oxygen atom, a sulfur atom, or an NH group, the divalent (C1-C16)alkylene radical being optionally substituted with at least one radical chosen from hydroxyl or a radical of formula (Z″):
• wherein in formula (Z″):
• Y1b, Y2b, Y2c, R1b, R2b and R3b have, respectively and independently, the same meanings as that of Y1, Y2, R1, R2 and R3;
• ALK is a (C1-C6)alkylene radical (divalent radical);
• and p is equal to 0 or 1;
• in formula (Z′), the symbol represents the point of attachment between alk and Y2;
• and
• in formula (Z″), the symbol represents the point of attachment between (Y2)p and ALK.

A multi-compartment device comprising:

• one or two compartments containing:
• a first ingredient i) comprising at least one compound of formula (I),
• and
• a second ingredient ii) comprising at least one polymerizable molecule chosen from compounds of formula (II), (IIa), (IIb) or (IIc);
• and
• a separate compartment comprising an artificial-light-emitting device providing an artificial light radiation with a wavelength ranging from 360 nm to 600 nm;
• wherein the first ingredient i) and the second ingredient ii) are contained together in one compartment or separately in two compartments;
• wherein in formula (I):
• R1, R2, R3 and R4, which may be identical or different, are chosen from a hydrogen atom, a halogen atom, or a group chosen from hydroxyl, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkylthio, (di)(C1-C6)(alkyl)amino, nitro(so);
• R5 is chosen from a hydrogen atom or a (C1-C8)alkyl group optionally substituted with at least one group chosen from i) hydroxyl, ii) R6—C(Y″)—O— with R6 being chosen from a hydrogen atom, a (C1-C4)alkyl group, or an aryl(C1-C4)alkyl group, and Y″ is chosen from an oxygen atom, a sulfur atom, or N(R7), wherein R7 is chosen from a hydrogen atom or a (C1-C4)alkyl group, iii) phosphoric (HO)2P(O)—O—, iv) —O—[(HO)P(O)—O]n-Suc-Het, wherein Suc is chosen from a divalent sugar group, and Het is chosen from a heteroaryl group, n being an integer equal to 0, 1 or 2;
• X is chosen from a nitrogen atom or a methylene group C(R8), wherein R8 is chosen from a hydrogen atom or a (C1-C4)alkyl group;
• X′ is chosen from an oxygen atom or a group NR9, wherein R9 is chosen from a hydrogen atom or a (C1-C6)alkyl group;
• and
• Y and Y′, which may be identical or different, are chosen from an oxygen atom, a sulfur atom, or a group NR10, wherein R10 is chosen from a hydrogen atom or a (C1-C6)alkyl group;
• and
• in formulae (II), (IIa), (IIb) and (IIc):
• R1 and R2, which may be identical or different, are chosen from a hydrogen atom, a (C1-C8)alkyl group, or a (C2-C8)alkenyl group, wherein the (C1-C8)alkyl and the (C2-C8)alkenyl groups are:
• optionally interrupted with at least one heteroatom chosen from 0, S, or N(R5), wherein R5 is chosen from a hydrogen atom or a (C1-C4)alkyl group, and/or
• optionally substituted with at least one radical chosen from the following radicals:
• hydroxyl, (di)(C1-C4)(alkyl)amino, (C1-C4)alkoxy or —C(Y′1)—Y′2—R′4;
• R3 is chosen from a hydrogen atom, a (C1-C8)alkyl group, a (C2-C8)alkenyl group, or a —C(Y′1)—Y′2—R′4 group;
• Y1, Y2, Y′1 and Y′2, which may be identical or different, are chosen from an oxygen atom, a sulfur atom, or N(R5), wherein R5 is chosen from a hydrogen atom or a (C1-C4)alkyl group;
• and
• R4 and R′4, which may be identical or different, are chosen from a hydrogen atom or a (C1-C16)alkyl group optionally substituted with at least one radical, which may be identical or different, chosen from the following radicals:
• a) amino (NH2), or mono- or di(C1-C4)alkylamino, b) hydroxyl (OH), c) SO3H, d) carboxyl (CO2H), e) cyano, f) (poly)(halo)(C1-C4)alkyl, or g) (C1-C4)alkoxycarbonyl;
• wherein the alkyl radical is optionally interrupted with at least one heteroatom;
• Z is chosen from a radical R4 or a radical (Z′) of formula:
• wherein in formula (Z′):
• Y1a, Y2a, R1a, R2a and R3a have, respectively and independently, the same meanings as that of Y1, Y2, R1, R2 and R3;
• alk is a divalent (C1-C16)alkylene radical optionally interrupted with an oxygen atom, a sulfur atom, or an NH group, wherein the divalent (C1-C16)alkylene radical is optionally substituted with one or more radicals chosen from hydroxyl or a radical of formula (Z″):
• wherein in formula (Z″):
• Y1b, Y2b, Y2c, R1b, R2b and R3b have, respectively and independently, the same meanings as that of Y1, Y2, R1, R2 and R3, ALK is a (C1-C6)alkylene radical (divalent radical), and p is equal to 0 or 1;
• in formula (Z′), the symbol represents the point of attachment between alk and Y2;
• and
• in formula (Z″), the symbol represents the point of attachment between (Y2)p and ALK.