Para-phenylenediamine derivatives containing a pyrrolidyl group, and use of these derivatives for coloring keratin fibers
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
A61Q-005/10
C07D-401/04
C07D-401/00
C07D-413/04
C07D-413/00
C07D-207/14
C07D-207/00
C07D-403/04
C07D-403/00
출원번호
US-0612986
(2003-07-07)
우선권정보
FR-02 08514(2002-07-05)
발명자
/ 주소
Sabelle,St챕phane
Ramos,Laure
LeDuc,Madeleine
출원인 / 주소
L'Oreal
대리인 / 주소
Finnegan, Henderson, Farabow, Garrett &
인용정보
피인용 횟수 :
0인용 특허 :
63
초록▼
The invention relates to novel pyrrolidyl-substituted para-phenylenediamine derivatives, to dye compositions containing them and to the process for dyeing keratin fibers using these compositions. The present invention makes it possible in particular to obtain a chromatic, strong, relatively unselect
The invention relates to novel pyrrolidyl-substituted para-phenylenediamine derivatives, to dye compositions containing them and to the process for dyeing keratin fibers using these compositions. The present invention makes it possible in particular to obtain a chromatic, strong, relatively unselective and resistant coloration of keratin fibers.
대표청구항▼
What is claimed is: 1. A compound chosen from para-phenylenediamine derivatives substituted with a pyrrolidyl group, wherein said pyrrolidyl-substituted para-phenylenediamine derivatives are chosen from derivatives corresponding to formula (I), and the addition salts thereof, wherein: n is an in
What is claimed is: 1. A compound chosen from para-phenylenediamine derivatives substituted with a pyrrolidyl group, wherein said pyrrolidyl-substituted para-phenylenediamine derivatives are chosen from derivatives corresponding to formula (I), and the addition salts thereof, wherein: n is an integer from 0 to 4, provided that when n is greater than or equal to 2, then the radicals R1 may be identical or different, R1 is chosen from halogen atoms; saturated and unsaturated, aliphatic and alicyclic C1-C6 hydrocarbon-based chains, wherein at least one carbon atom of the hydrocarbon-based chain may be replaced with at least one entity chosen from oxygen, nitrogen, silicon and sulphur atoms and from SO and SO2 groups, provided that the radical R1 does not comprise a peroxide bond or a diazo, nitro or nitroso radical; and further wherein the hydrocarbon-based chain may be substituted with at least one group chosen from halogen atoms and hydroxyl, amino, mono-(C1-C4)alkylamino, di(C1-C4)alkylamino and tri(C1-C4)alkylammonium radicals; Y is chosen from a covalent bond and a linear or branched C1-C14 alkylene chain, wherein at least one carbon atom of the chain may be replaced with at least one atom chosen from oxygen, nitrogen, silicon and sulphur atoms or with a group chosen from SO and SO2 groups; wherein the chain may be substituted with at least one radical chosen from hydroxyl, C1-C6 alkoxy, amino, C1-C6 alkylamino and C1-C6 dialkylamino radicals; and further wherein the chain may bear at least one ketone functional group, and R2 is chosen from 3-to 7-membered saturated and unsaturated carbocycles and heterocycles, which may be substituted with at least one radical chosen from C1-C6 alkyl and C 1-C6 hydroxyalkyl radicals. 2. The compound according to claim 1, wherein n is equal to 0 or 1. 3. The compound according to claim 1, wherein R1 is chosen from halogen atoms, C1-C4 alkyl radicals, C 1-C4 hydroxyalkyl radicals, C1-C4 aminoalkyl radicals, C1-C4 alkoxy radicals and C 1-C4 hydroxyalkoxy radicals. 4. The compound according to claim 3, wherein R1 is a radical chosen from methyl, hydroxymethyl, 2-hydroxyethyl, 1,2-dihydroxyethyl, methoxy, isopropyloxy and 2-hydroxyethoxy radicals. 5. The compound according to claim 1, wherein Y is a covalent bond. 6. The compound according to claim 1, wherein Y is chosen from C1-C8 alkylene chains, which may comprise at least one unit chosen from--O--,--NR'--and--NR'CO--wherein R' is chosen from hydrogen atoms and C1-C4 alkyl radicals. 7. The compound according to claim 1, wherein Y is chosen from--O--,--NR'--,--S--,--SO--and--SO2--. 8. The compound according to claim 1, wherein R2 is a nitrogenous heterocycle. 9. The compound according to claim 8, wherein R2 is chosen from imidazole, pyrrolidine, piperazine, piperidine, triazole, diazepan and pyrazole rings. 10. The compound according to claim 8, wherein R2 is linked to Y via one of the nitrogen atoms of the nitrogenous heterocycle. 11. The compound according to claim 1, wherein R2 is a carbocycle chosen from C4-C7 cycloalkyls. 12. The compound according to claim 1, wherein R2 is a phenyl radical. 13. The compound according to claim 1, chosen from 4-(3-imidazol-1-ylpyrrolid-1-yl)phenylamine, 4-(3-[1,2,4]triazol-1-ylpyrrolid-1-yl)phenylamine, 4-[1,3']bipyrrolid-1'-ylphenylamine, 4-[3-(4-methylpiperazin-1-yl)pyrrolid-1-yl]phenylamine, 4-[3-(4-methyl[1,4]diazepan-1-yl)pyrrolid-1-yl]phenylamine, 4-{3-[2-(4-methyl[1,4]d iazepan-1-yl)ethoxy]pyrrolid-1-yl} phenylamine, 4-{3-[2-(4-methylpiperazin-1-yl )ethoxy]pyrrolid-1-yl} phenylamine, 4-[3-(2-pyrrolid-1-ylethoxy)pyrrolid-1-yl]phenylamine, 4-[3-(2-piperid-1-ylethoxy)pyrrolid-1-yl]phenylamine, [1-(4-aminophenyl)pyrrolid-3-yl]-3-imidazol-1-ylpropyl)amine, 2-methyl-[1-(4-aminophenyl)pyrrolid-3-yl](3-imidazol-1-ylpropyl)amine, 4-(3-imidazol-1-ylpyrrolid-1-yl)-2-methylphenylamine, 2-methyl-4-(3-[1, 2,4]triazol-1-ylpyrrolid-1-yl )phenylamine, 4-[1,3']bipyrrolid-1'-yl-2-methylphenylamine, 2-methyl-4-[3-(4-methylpiperazin-1-yl)pyrrolid-1-yl] phenylamine, 2-methyl-4-[3-(4-methyl-[1,4]diazepan-1-yl)pyrrolid-1-yl] phenylamine, 2-methyl-4-{3-[2-(4-methyl-[1,4]diazepan-1-yl)ethoxy]pyrrolid-1-yl}phenylamine, 2-methyl-4-{3-[2-(4-methylpiperazin-1-yl)ethoxy]pyrrolid-1-yl} phenylamine, 4-(3-pyrazol-1-ylpyrrolid-1-yl)phenylamine, 2-methyl-4-(3-pyrazol-1-ylpyrrolid-1-yl)phenylamine, 2-methyl-4-[3-(2-pyrrolid-1-ylethoxy)pyrrolid-1-yl] phenylamine and 2-methyl-4-[3-(2-piperid-1-ylethoxy)pyrrolid-1-yl]phenylamine. 14. The compound according to claim 8, chosen from 4-(3-imidazol-1-yl-pyrrolid-1-yl)phenylamine, 4-[1,3']bipyrrolid-1'-yl-phenylamine, 4-[3-(4-methylpiperazin-1-yl)pyrrolid-1-yl]phenylamine, 4-{3-[2-(4-methylpiperazin-1-yl )ethoxy]pyrrolid-1-yl} phenylamine, 4-[3-(2-pyrrolid-1-ylethoxy)pyrrolid-1-yl]phenylamine, 4-[3-(piperid-1-yl)pyrrolid-1-yl]phenylamine, 4-[3-(2-piperid-1-ylethoxy)pyrrolid-1-yl]phenylamine, [1-(4-aminophenyl)pyrrolid-3-yl](3-imidazol-1-ylpropyl)amine, 2-methyl-[1-(4-aminophenyl)pyrrolid-3-yl](3-imidazol-1-ylpropyl)amine, 4-(3-imidazol-1-ylpyrrolid-1-yl)-2-methylphenylamine, 4-[1,3']bipyrrolid-1'-yl-2-methylphenylamine, 2-methyl-4-[3-(4-methylpiperazin-1-yl)pyrrolid-1-yl] phenylamine, 2-methyl-4-[3-(piperid-1-yl)pyrrolid-1-yl]phenylamine, 2-methyl-4-{3-[2-(4-methylpiperazin-1-yl)ethoxy]pyrrolid-1-yl} phenylamine, 4-(3-pyrazol-1-ylpyrrolid-1-yl)phenylamine, 2-methyl-4-(3-pyrazol-1-ylpyrrolid-1-yl)phenylamine, 2-methyl-4-[3-(2-pyrrolid-1-ylethoxy)pyrrolid-1-yl] phenylamine, and 2-methyl-4-[3-(2-piperid-1-ylethoxy)pyrrolid-1-yl]phenylamine. 15. A dye composition comprising at least one oxidation base chosen from pryrrolidyl-substituted para-phenylenediamine derivatives chosen from derivatives corresponding to formula (I), and the addition salts thereof wherein n is an integer from 0 to 4, provided that when n is greater than or equal to 2, then the radicals R1 may be identical or different, R1 is chosen from halogen atoms; saturated and unsaturated, aliphatic and alicyclic C1-C6 hydrocarbon-based chains, wherein at least one carbon atom of the hydrocarbon-based chain may be replaced with at least one entity chosen from oxygen, nitrogen, silicon and sulphur atoms and SO and SO2 groups, provided that the radical R1 does not comprise a peroxide bond or a diazo, nitro or nitroso radical; and further wherein the hydrocarbon-based chain may be substituted with at least one group chosen from halogen atoms and hydroxyl, amino, mono-(C1-C4) alkylamino, di(C1-C4)alkylamino and tri(C1-C4)alkylammonium radicals; Y is chosen from a covalent bond and a linear or branched C1-C14 alkylene chain, wherein at least one carbon atom of the chain may be replaced with at least one atom chosen from oxygen, nitrogen, silicon and sulphur atoms or with a group chosen from SO and SO2 groups; wherein the chain may be substituted with at least one radical chosen from hydroxyl, C1-C6 alkoxy, amino, C1-C6 alkylamino and C1-C6 dialkylamino radicals; and further wherein the chain may bear at least one ketone functional group, and R2 is chosen from 3-to 7-membered saturated and unsaturated carbocycles and heterocycles, which may be substituted with at least one radical chosen from C1-C6 alkyl and C 1-C6 hydroxyalkyl radicals. 16. The dye composition according to claim 15, further comprising at least one coupler chosen from meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers, heterocyclic couplers, and the addition salts thereof. 17. The dye composition according to claim 15, comprising at least one additional oxidation base chosen from para-phenylenediamines, bis(phenyl)-alkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases, and the addition salts thereof, provided that the at least one additional oxidation base does not comprise at least one compound chosen from pryrrolidyl-substituted para-phenylenediamine derivatives chosen from derivatives corresponding to formula (I), and the addition salts thereof. 18. The dye composition according to claim 17, wherein each of the oxidation bases is present in an amount ranging approximately from 0.001% to 10% by weight, relative to the total weight of the composition. 19. The dye composition according to claim 16, wherein the at least one coupler is present in an amount ranging approximately from 0. 001% to 10% by weight, relative to the total weight of the dye composition. 20. The dye composition according to claim 17, further comprising at least one coupler chosen from meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers and heterocyclic couplers, and the addition salts thereof. 21. The dye composition according to claim 20, wherein said at least one coupler is present in an amount ranging approximately from 0. 01% to 10% by weight, relative to the total weight of the composition. 22. The dye composition according to claim 15, further comprising a cosmetically acceptable medium that is suitable for dyeing keratin fibers. 23. The dye composition according to claim 15, further comprising at least one oxidizing agent. 24. A process for the oxidation dyeing of keratin fibers, comprising applying to said keratin fibers, in the presence of an oxidizing agent, for a time that is sufficient to develop a desired coloration, an oxidation dyeing composition comprising at least one oxidation base, wherein said at least one oxidation base comprises at least one compound chosen from pryrrolidyl-group-substituted para-phenylenediamine derivatives chosen from derivatives corresponding to formula (I), and the addition salts thereof wherein n is an integer from 0 to 4, provided that when n is greater than or equal to 2, then the radicals R1 may be identical or different, R1 is chosen from halogen atoms; saturated and unsaturated, aliphatic and alicyclic C1-C6 hydrocarbon-based chains, wherein at least one carbon atom of the hydrocarbon-based chain may be replaced with at least one entity chosen from oxygen, nitrogen, silicon and sulphur atoms and SO and SO2 groups, provided that the radical R1 does not comprise a peroxide bond or a diazo, nitro or nitroso radical; and further wherein the hydrocarbon-based chain may be substituted with at least one group chosen from halogen atoms and hydroxyl, amino, mono-(C1-C4) alkylamino, di(C1-C4)alkylamino and tri(C1-C4)alkylammonium radicals; Y is chosen from a covalent bond and a linear or branched C1-C14 alkylene chain, wherein at least one carbon atom of the chain may be replaced with at least one atom chosen from oxygen, nitrogen, silicon and sulphur atoms or with a group chosen from SO and SO2 groups; wherein the chain may be substituted with at least one radical chosen from hydroxyl, C1-C6 alkoxy, amino, C1-C6 alkylamino and C1-C6 dialkylamino radicals; and further wherein the chain may bear at least one ketone functional group, and R2 is chosen from 3-to 7-membered saturated and unsaturated carbocycles and heterocycles, which may be substituted with at least one radical chosen from C1-C6 alkyl and C 1-C6 hydroxyalkyl radicals. 25. The dyeing process according to claim 24, wherein the at least one oxidizing agent is chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts, peracids and oxidase enzymes. 26. A multi-compartment device for the oxidation dyeing of keratin fibers, wherein a first compartment contains an oxidation dyeing composition and a second compartment contains at least one oxidizing agent, wherein said oxidation dyeing composition comprises at least one oxidation base chosen from pryrrolidyl-substituted para-phenylenediamine derivatives chosen from derivatives corresponding to formula (I), and the addition salts thereof wherein n is an integer from 0 to 4, provided that when n is greater than or equal to 2, then the radicals R1 may be identical or different, R1 is chosen from halogen atoms; saturated and unsaturated, aliphatic and alicyclic C1-C6 hydrocarbon-based chains, wherein at least one carbon atom of the hydrocarbon-based chain may be replaced with at least one entity chosen from oxygen, nitrogen, silicon and sulphur atoms and SO and SO2 groups, provided that the radical R1 does not comprise a peroxide bond or a diazo, nitro or nitroso radical; and further wherein the hydrocarbon-based chain may be substituted with at least one group chosen from halogen atoms and hydroxyl, amino, mono-(C1-C4) alkylamino, di(C1-C4)alkylamino and tri(C1-C4)alkylammonium radicals; Y is chosen from a covalent bond and a linear or branched C1-C14 alkylene chain, wherein at least one carbon atom of the chain may be replaced with at least one atom chosen from oxygen, nitrogen, silicon and sulphur atoms or with a group chosen from SO and SO2 groups; wherein the chain may be substituted with at least one radical chosen from hydroxyl, C1-C6 alkoxy, amino, C1-C6 alkylamino and C1-C6 dialkylamino radicals; and further wherein the chain may bear at least one ketone functional group, and R2 is chosen from 3-to 7-membered saturated and unsaturated carbocycles and heterocycles, which may be substituted with at least one radical chosen from C1-C6 alkyl and C 1-C6 hydroxyalkyl radicals.
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이 특허에 인용된 특허 (63)
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