Patent FR-2872160-A1 (FR)
Title: New cationic diazo compounds useful as direct dye and for dyeing wet or dry keratin fibers
Inventor: GREAVES ANDREW
IPC: A61K8/49
Filed: 2004-06-23
Abstract: New cationic diazo compounds and their acid addition salts are claimed. Cationic diazo compounds and their acid addition salts, are new. Dye 1- L'K' - Dye 2(I) and their acid addition salts, are new. Dye 1W 3-N=N-W 2-W 1-* or W 3-N=N-W 2a(W 1a)-*; Dye 2W 4-N=N-W 5-W 6-* or W 4-N=N-W 5a(W 6a)-*; W 1and W 6-NR 1- or -O-; R 1H and optionally saturated, optionally aromatic, optionally substituted 1-20C hydrocarbon-based chains, which optionally form at least one optionally substituted 3- to 7-membered carbon-based rings, optionally interrupted with at least one hetero atom or with at least one group bearing at least one hetero atom; W 1aand W 6a-NR 1aR 2aor -OR 3a; R 1a, R 2aand R 3aH and optionally saturated, optionally aromatic, optionally substituted 1-20C hydrocarbon-based chains, which can form at least one optionally substituted 3- to 7-membered carbon-based ring, optionally interrupted with at least one hetero atom or with at least one group bearing at least one hetero atom;or NR 1a+R 2aan optionally substituted 5- or 7-membered heterocycle optionally comprising another nitrogen or non-nitrogen hetero atom; W 2, W 5, W 2aand W 5agroups of formulae (i) to (iii); X 1N or CR 7; X 2N or CR 8; Z 1N or CR 10; Z 2N or CR 11; R 4, R 5, R 7, R 8, R 10and R 11G 1, H or a bond from W 2ato W 1aor to the group L'K', or from W 5ato W 6aor to the group L'K'; R 6and R 6aG 1; G 1T 1, hydroxyl, 1-4C alkoxy, 2-4C (poly)hydroxyalkoxy, RO-CO-, RCO-O-, amino (optionally substituted by at least one 1-4C alkyl (optionally bearing at least one hydroxyl, and possibly forming with the nitrogen atom to which they are attached, 5- or 6-membered heterocycle optionally bearing another nitrogen or non-nitrogen hetero atom)), RCO-NR-, (R') 2N-CO, N(R') 2-CO-NR' a-, (R') 2N-SO 2-, R'SO 2-NR' a-, (R' a) 2N-C(=NH 2+>(X ->))-NR'-, nitro, cyano or halo; T 1linear or branched, optionally saturated, optionally aromatic, optionally substituted 1-16C hydrocarbon-based chains, which optionally form at least one optionally substituted 3- to 7-membered carbon-based ring, optionally interrupted with at least one hetero atom or with at least one group bearing at least one hetero atom; R : 1-4C alkyl; R' and R' aH or 1-4C alkyl; a' : bond from W 2, W 5, W 2aor W 5ato the azo group -N = N-; b' : bond from W 2to W 1, from W 5to W 6, from W' 2to W' 1or to the group L'K', or from W' 5to W' 6or to the group L'K'; R 9H, linear or branched, optionally saturated, optionally aromatic, optionally substituted 1-16C hydrocarbon-based chains, which can form at least one optionally substituted 3- to 7-membered carbon-based ring; n and n' : integers; n+n' : = 6; W 3and W 4cationic heteroaromatic radicals selected from formulae (ia) to (ih) or (ij) to (il); R 4aG 1;or R 4a+R 4aoptionally aromatic, 5- or 6-membered secondary ring, optionally substituted by at least one of H, hydroxyl, 1-4C alkyl radicals, 1-4C alkoxy, 2-4C(poly)hydroxyalkoxy, amino (optionally substituted by at least one 1-4C alkyl, optionally bearing at least one hydroxyl); R 5aT 1; R 7a1-4C alkyl, phenyl or benzyl (all optionally substituted); p : 0 to 4; r : 0 to 2; t : 0 to 3; L'K' : optionally saturated, optionally substituted 2-40C hydrocarbon-based chains, optionally interrupted with at least one hetero atom or group comprising at least one hetero atom; X ->anions. The group R 1of W 1and W 6, together or separately, optionally form with all or part of the group L'K' and with the nitrogen atom to which each is attached optionally saturated, optionally aromatic, optionally substituted 5- to 7-membered heterocycle. The radicals R 1a, R 2aor R 3aof W 1aand W 6a, together or separately, optionally form, with all or part of the group L'K' and with the nitrogen or oxygen atom to which each is attached, optionally saturated, aromatic or non-aromatic, optionally substituted 5- to 7-membered heterocycle. The groups R 4-R 8, R 6a, R 10and R 11, independently of each other, optionally form, with all or some of the groups W 1aor W 6a, or alternatively, all or some of the groups W 1or W 6, optionally saturated, optionally aromatic, optionally substituted 5- to 7-membered heterocycle. The bond c' links the cationic radical (ia) to (ih) and (ij) to (ik) to the azo group, where the bond is optionally on the main or secondary ring. Provided that: (1) Dye 1and Dye 2are such that the compound of formula (I) is not symmetrical; (2) when the main ring does not bear the maximum number of substituents, then the unsubstituted position(s) bear(s) a nitrogen atom; with the condition that at least one of the two groups W 3and W 4are not selected from unsubstituted imidazolium groups; (3) the group L'K' does not comprise any nitro, nitroso or peroxo groups or bonds; (4) if L'K' is linked to W' 2or W' 5, then L'K' may end with a hetero atom or group bearing at least one hetero atom; and (5) if L'K' is linked to W 6or W 1, then L'K' may end with a group bearing at least one of -CO- or -SO 2-. Independent claims are included for the following: (1) a dye composition comprising, in a medium that is suitable for dyeing keratin fibers, at least one direct dye selected from the compounds (I) and their acid addition salts; and (2) a multi-compartment kit comprising at least one first compartment comprising the dye composition and at least one second compartment comprising at least one oxidizing composition comprising at least one oxidizing agent. [Image] [Image] [Image] [Image] [Image].