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US 11,142,498 B2Granted
Keratin dyeing compounds, compositions containing them, and method and use thereof
AssigneeWella Operations US, LLC
InventorBryan P. Murphy
Life of this patent
Estimating the term…
Abstract
A novel class of 3-halo-1H-indol-4-amine derivatives, particularly for dyeing keratin fibers, the azomethine dyes formed from them, their uses as a coupler for dyeing keratin fibers, hair dyeing compositions comprising them, method of dyeing hair thereof, and a hair dyeing kit thereof are disclosed. The products of the oxidative coupling with hair dye primary intermediates, particularly pyrazole derivative, a p-phenylenediamine derivative, a p-aminophenol derivative, have improved fastness properties over currently used violet-blue to blue azomethine dyes.
Claims19
A 3-halo-1H-indol-4-amine compound of general formula (I)
- wherein radical X is a halogen atom selected from the group consisting of chlorine or bromine;
- wherein radicals R1 and R3 are the same or different and are selected from the group consisting of:
- (a) N-linked monovalent substituents selected from the group consisting of:
- (i) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems;
- (ii) substituted or unsubstituted, mono- or poly-cyclic aliphatic;
- (iii) an aromatic ring or 5- or 6-membered heteroaromatic rings having at least one nitrogen, oxygen or sulfur atom;
- and,
- (iv) substituted or unsubstituted, mono- or polyhydroxy-, mono- or polyamino-, mono- or polyfluoro-alkyl systems, or mixtures thereof;
- wherein said systems of (i) and (ii) comprise from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from the group consisting of O, S, N, P, and Si;
- (b) hydrogen;
- (c) a linker group (L) between one of the radical R1 or R3 of a first compound of formula (I) and between one of the radical R1 or R3 of a second compound of formula (I), both compounds forming therefore a dimeric structure, wherein the linker group is of general formula (L)
- wherein
- (i) a, c, e and g are each independently an integer from 0 to 3, provided that the sum of a, c, e and g is greater than or equal to 2;
- b, d and f are each independently 0 or 1;
- and R50, R51, R52, R53, R54, R55, R56 and R57 are each independently hydrogen or C1-C2 alkyl group;
- (ii) U is an aromatic ring, alkenyl or alkynyl moiety;
- (iii) V is O, N or S;
- and
- (iv) W is a cyclic aliphatic ring;
- wherein radicals R2 and R5 are the same or different and are selected from the group consisting of:
- (a) C-linked monovalent substituents selected from the group consisting of:
- (i) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems;
- (ii) substituted or unsubstituted, mono- or poly-cyclic aliphatic;
- (iii) halogen atom;
- (iv) a boronic acid group, a boronic ester group;
- (v) an aromatic ring or 5- or 6-membered heteroaromatic rings having at least one nitrogen, oxygen or sulfur atom;
- and,
- (vi) substituted or unsubstituted, mono- or polyhydroxy-, mono- or polyamino-, mono- or polyfluoro-alkyl systems, or mixtures thereof;
- wherein said systems of (i) and (ii) comprise from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from the group consisting of O, S, N, P, and Si;
- (b) S-linked monovalent substituents selected from the group consisting of SA1, SO2A1, SO3A1, SSA1, SOA1, SO2NA1A2, SNA1A2, and SONA1A2;
- (c) O-linked monovalent substituents selected from the group consisting of OA1, and ONA1A2;
- (d) N-linked monovalent substituents selected from the group consisting of NA1A2, (NA1A2A3)+, NA1OA2, NA1SA2, N═NA1, N═NOA1, NA1CN, and NA1NA2A3;
- (e) monovalent substituents selected from the group consisting of COOA1, CONA12, CONA1COA2, and C(═NA1)NA1A2;
- (f) fluoroalkyl monovalent substituents selected from the group consisting of mono-, poly-, and per-fluoro alkyl systems comprising from about 1 to about 12 carbon atoms and from about 0 to about 4 heteroatoms;
- and
- (g) hydrogen;
- wherein A1, A2, and A3 are monovalent and are independently selected from the group consisting of:
- H;
- substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems;
- substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems;
- and substituted or unsubstituted, mono-, poly-, per-fluoro alkyl systems or A1 and A2 together with nitrogen atom to which they are bound form a ring, wherein said systems comprise from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from the group consisting of O, S, N, P, and Si;
- wherein one of radicals R4 or R6 is selected from the group consisting of a hydrogen atom and/or a nucleofuge group;
- wherein the nucleofuge group is selected from the group consisting of an alkoxy radical, an alkoxyalkyl radical, alkoxycarbonyl radical, an aryloxy group, a heteroaryloxy radical, an aryloxycarbonylamino radical, or an aryloxycarbonyl radical;
- wherein the other radical R6 or R4 is selected from the group consisting of:
- (a) C-linked monovalent substituents selected from the group consisting of:
- substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems;
- (ii) substituted or unsubstituted, mono- or poly-cyclic aliphatic;
- (iii) halogen atom;
- (iv) a boronic acid group, a boronic ester group;
- (v) an aromatic ring or 5- or 6-membered heteroaromatic rings having at least one nitrogen, oxygen or sulfur atom;
- and,
- (vi) substituted or unsubstituted, mono- or polyhydroxy-, mono- or polyamino-, mono- or polyfluoro- alkyl systems, or mixtures thereof;
- wherein said systems of (i) and (ii) comprise from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from the group consisting of O, S, N, P, and Si;
- (b) S-linked monovalent substituents selected from the group consisting of SA1, SO2A1, SO3A1, SSA1, SOA1, SO2NA1A2, SNA1A2, and SONA1A2;
- (c) O-linked monovalent substituents selected from the group consisting of ONA1A2;
- (d) monovalent substituents selected from the group consisting of COOA1, CONA12, CONA1COA2, and C(═NA1)NA1A2;
- (e) fluoroalkyl monovalent substituents selected from the group consisting of mono-, poly-, and per-fluoro alkyl systems comprising from about 1 to about 12 carbon atoms and from about 0 to about 4 heteroatoms;
- and
- wherein R4 and R6 are not both selected from hydrogen;
- (f) hydrogen;
- wherein A1, A2, and A3 are monovalent and are independently selected from the group consisting of:
- H;
- substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems;
- substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems;
- and substituted or unsubstituted, mono-, poly-, per-fluoro alkyl systems or A1 and A2 together with nitrogen atom to which they are bound form a ring;
- wherein said systems comprise from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from the group consisting of O, S, N, P, and Si;
- and
- their salts thereof;
- wherein the 3-halo-1H-indol-4-amine compound of formula (1) is not the compound of formula (I.01) or of formula (I.02)
66 more elements
A method of dyeing keratin fibers comprising use of a 3-halo-1H-indol-4-amine compound, as a coupler;
- wherein the 3-halo-1H-indol-4-amine compound is a compound of general formula (I)
- wherein radical X is a halogen atom selected from the group consisting of chlorine or bromine;
- wherein radicals R1 and R3 are the same or different and are selected from the group consisting of:
- (a) N-linked monovalent substituents selected from the group consisting of:
- (i) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems;
- (ii) substituted or unsubstituted, mono- or poly-cyclic aliphatic;
- (iii) an aromatic ring or 5- or 6-membered heteroaromatic rings having at least one nitrogen, oxygen or sulfur atom;
- and,
- (iv) substituted or unsubstituted, mono- or polyhydroxy-, mono- or polyamino-, mono- or polyfluoro-alkyl systems, or mixtures thereof;
- wherein said systems of (i) and (ii) comprise from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from the group consisting of O, S, N, P, and Si;
- (b) hydrogen;
- (c) a linker group (L) between one of the radical R1 or R3 of a first compound of formula (I) and between one of the radical R1 or R3 of a second compound of formula (I), both compounds forming therefore a dimeric structure, wherein the linker group is of general formula (L)
- wherein
- (i) a, c, e and g are each independently an integer from 0 to 3, provided that the sum of a, c, e and g is greater than or equal to 2;
- b, d and f are each independently 0 or 1;
- and R50, R51, R52, R53, R54, R55, R56 and R57 are each independently hydrogen or C1-C2 alkyl group;
- (ii) U is an aromatic ring, alkenyl or alkynyl moiety;
- (iii) V is O, N or S;
- and
- (iv) W is a cyclic aliphatic ring;
- wherein radicals R2 and R5 are the same or different and are selected from the group consisting of:
- (a) C-linked monovalent substituents selected from the group consisting of:
- (i) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems;
- (ii) substituted or unsubstituted, mono- or poly-cyclic aliphatic;
- (iii) halogen atom;
- (iv) a boronic acid group, a boronic ester group;
- (v) an aromatic ring or 5- or 6-membered heteroaromatic rings having at least one nitrogen, oxygen or sulfur atom;
- and,
- (vi) substituted or unsubstituted, mono- or polyhydroxy-, mono- or polyamino-, mono- or polyfluoro-alkyl systems, or mixtures thereof;
- wherein said systems of (i) and (ii) comprise from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from the group consisting of O, S, N, P, and Si;
- (b) S-linked monovalent substituents selected from the group consisting of SA1, SO2A1, SO3A1, SSA1, SOA1, SO2NA1A2, SNA1A2, and SONA1A2;
- (c) O-linked monovalent substituents selected from the group consisting of OA1, and ONA1A2;
- (d) N-linked monovalent substituents selected from the group consisting of NA1A2, (NA1A2A3)+, NA1OA2, NA1SA2, N═NA1, N═NOA′, NA1CN, and NA1NA2A3;
- (e) monovalent substituents selected from the group consisting of COOA1, CONA12, CONA1COA2, and C(═NA1)NA1A2;
- (f) fluoroalkyl monovalent substituents selected from the group consisting of mono-, poly-, and per-fluoro alkyl systems comprising from about 1 to about 12 carbon atoms and from about 0 to about 4 heteroatoms;
- and
- (g) hydrogen;
- wherein A1, A2, and A3 are monovalent and are independently selected from the group consisting of:
- H;
- substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems;
- substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems;
- and substituted or unsubstituted, mono-, poly-, per-fluoro alkyl systems or A1 and A2 together with nitrogen atom to which they are bound form a ring;
- wherein said systems comprise from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from the group consisting of O, S, N, P, and Si;
- wherein one of radicals R2 or R4 is selected from the group consisting of a hydrogen atom and/or a nucleofuge group;
- wherein the other radical R4 or R2 or is selected from the group consisting of:
- (a) C-linked monovalent substituents selected from the group consisting of:
- (i) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems;
- (ii) substituted or unsubstituted, mono- or poly-cyclic aliphatic;
- (iii) halogen atom;
- (iv) a boronic acid group, a boronic ester group;
- (v) an aromatic ring or 5- or 6-membered heteroaromatic rings having at least one nitrogen, oxygen or sulfur atom;
- and,
- (vi) substituted or unsubstituted, mono- or polyhydroxy-, mono- or polyamino-, mono- or polyfluoro-alkyl systems, or mixtures thereof;
- wherein said systems of (i) and (ii) comprise from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from the group consisting of O, S, N, P, and Si;
- (b) S-linked monovalent substituents selected from the group consisting of SA1, SO2A1, SO3A1, SSA1, SOA1, SO2NA1A2, SNA1A2, and SONA1A2;
- (c) O-linked monovalent substituents selected from the group consisting of ONA1A2;
- (d) monovalent substituents selected from the group consisting of COOA1, CONA12, CONA1COA2, C(═NA1)NA1A2, and CN;
- (e) fluoroalkyl monovalent substituents selected from the group consisting of mono-, poly-, and per-fluoro alkyl systems comprising from about 1 to about 12 carbon atoms and from about 0 to about 4 heteroatoms;
- and
- (f) hydrogen;
- wherein A1, A2, and A3 are monovalent and are independently selected from the group consisting of:
- H;
- substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems;
- substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems;
- and substituted or unsubstituted, mono-, poly-, per-fluoro alkyl systems or A1 and A2 together with nitrogen atom to which they are bound form a ring;
- wherein said systems comprise from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from the group consisting of O, S, N, P, and Si;
- and their salts thereof.
64 more elements
Dependencies are inferred from the claim text.