Back to results
US 2006/0123565 A9Published application
Para-phenylenediamine derivatives comprising a cyclic diaza group substituted with a cationic radical, and use of these derivatives for dyeing keratin fibers
AssigneeL'oreal
InventorsStephane Sabelle, Alain Genet, Madeleine Leduc
Life of this patent
Estimating the term…
Abstract
The disclosure relates to novel para-phenylenediamine derivatives containing a cyclic diaza group, substituted with a cationic radical, as well as to the dye compositions comprising them, and to the method of dyeing keratin fibers using these compositions. Tthe present invention may make it possible to obtain a chromatic, strong, relatively unselective and fast coloration on keratin fibers.
Claims40
A compound of formula (I), and the addition salts thereof
- wherein:
- a ranges from 0 to 4, it being understood that when a is greater than or equal to 2, then the radicals R1 may be identical or different,
- b ranges from 0 to 4, it being understood that when b is greater than or equal to 2, then the radicals R4 may be identical or different,
- c is equal to 0 or 1,
- R1 is chosen from a halogen atom;
- C1-C8 aliphatic and alicyclic, saturated and unsaturated hydrocarbon-based chains, wherein at least one carbon atom is optionally replaced with at least one entity chosen from oxygen, nitrogen, silicon, and sulphur atoms and an SO2 group;
- and an onium radical Z;
- with the proviso that the radical R1 does not comprise a peroxide bond or diazo, nitro or nitroso radicals,
- R2 comprises an onium radical Z, wherein an onium radical is a nitrogen-based quaternary radical,
- R3 is chosen from
- an alkyl radical;
- an alkenyl radical;
- an alkynyl radical;
- a hydroxyl radical;
- a hydroxyalkyl radical;
- an alkoxy radical;
- an alkoxyalkyl radical;
- an alkylcarbonyl radical;
- a hydroxyalkoxyalkyl radical;
- an amino radical;
- a monoalkylamino radical;
- a dialkylamino radical;
- an aminoalkyl radical;
- an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals;
- a hydroxyl radical;
- a aminoalkyl radical;
- a carboxyl radical;
- a carboxyalkyl radical;
- a carbamoyl radical;
- a carbamoylalkyl radical;
- an alkoxycarbonyl radical;
- a monoalkylaminocarbonyl radical;
- a dialkylaminocarbonyl radical;
- a monoalkylaminocarbonylalkyl radical;
- and
- a dialkylaminocarbonylalkyl radical;
- R4 is chosen from
- an alkyl radical;
- an alkenyl radical;
- an alkynyl radical;
- a hydroxyalkyl radical;
- an alkoxyalkyl radical;
- an alkylcarbonyl radical;
- a hydroxyalkoxyalkyl radical;
- an aminoalkyl radical;
- an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals;
- a hydroxyl radical;
- a aminoalkyl radical;
- a carboxyl radical;
- a carboxyalkyl radical;
- a carbamoyl radical;
- a carbamoylalkyl radical;
- an alkoxycarbonyl radical;
- a monoalkylaminocarbonyl radical;
- a dialkylaminocarbonyl radical;
- a monoalkylaminocarbonylalkyl radical;
- and
- a dialkylaminocarbonylalkyl radical.
55 more elements
The nitro derivatives of formula (I′)
- a ranges from 0 to 4, it being understood that when a is greater than or equal to 2, then the radicals R1 may be identical or different,
- b ranges from 0 to 4, it being understood that when b is greater than or equal to 2, then the radicals R4 may be identical or different,
- c is equal to 0 or 1,
- R1 is chosen from halogen atoms;
- C1-C8 aliphatic and alicyclic, saturated and unsaturated hydrocarbon-based chains, wherein at least one carbon atom is optionally replaced with at least one entity chosen from oxygen, nitrogen, silicon, and sulphur atoms and an SO2 group;
- and an onium radical Z;
- with the proviso that the radical R1 does not comprise a peroxide bond or diazo, nitro or nitroso radicals,
- R2 comprises an onium radical Z, wherein an onium radical is a nitrogen-based quaternary radical,
- R3 is chosen from
- an alkyl radical;
- an alkenyl radical;
- an alkynyl radical;
- a hydroxyl radical;
- a hydroxyalkyl radical;
- an alkoxy radical;
- an alkoxyalkyl radical;
- an alkylcarbonyl radical;
- a hydroxyalkoxyalkyl radical;
- an amino radical;
- a monoalkylamino radical;
- a dialkylamino;
- an aminoalkyl radical;
- an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals;
- a hydroxyl radical;
- a aminoalkyl radical;
- a carboxyl radical;
- a carboxyalkyl radical;
- a carbamoyl radical;
- a carbamoylalkyl radical;
- an alkoxycarbonyl radical;
- a monoalkylaminocarbonyl radical;
- a dialkylaminocarbonyl radical;
- a monoalkylaminocarbonylalkyl radical;
- and
- a dialkylaminocarbonylalkyl radical;
- R4 is chosen from
- an alkyl radical;
- an alkenyl radical;
- an alkynyl radical;
- a hydroxyalkyl radical;
- an alkoxyalkyl radical;
- an alkylcarbonyl radical;
- a hydroxyalkoxyalkyl radical;
- an aminoalkyl radical;
- an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals;
- a hydroxyl radical;
- a aminoalkyl radical;
- a carboxyl radical;
- a carboxyalkyl radical;
- a carbamoyl radical;
- a carbamoylalkyl radical;
- an alkoxycarbonyl radical;
- a monoalkylaminocarbonyl radical;
- a dialkylaminocarbonyl radical;
- a monoalkylaminocarbonylalkyl radical;
- and
- a dialkylaminocarbonylalkyl radical.
54 more elements
A dye composition comprising, as oxidation base, at least one compound of formula (I), and the addition salts thereof
- wherein:
- a ranges from 0 to 4, it being understood that when a is greater than or equal to 2, then the radicals R1 may be identical or different,
- b ranges from 0 to 4, it being understood that when b is greater than or equal to 2, then the radicals R4 may be identical or different,
- c is equal to 0 or 1,
- R1 is chosen from halogen atoms;
- C1-C8 aliphatic and alicyclic, saturated and unsaturated hydrocarbon-based chains, wherein at least one carbon atom is optionally replaced with at least one entity chosen from oxygen, nitrogen, silicon, and sulphur atoms and an SO2 group;
- and an onium radical Z;
- with the proviso that the radical R1 does not comprise a peroxide bond or diazo, nitro or nitroso radicals, R2 comprises an onium radical Z, wherein an onium radical is a nitrogen-based quaternary radical,
- R3 is chosen from
- an alkyl radical;
- an alkenyl radical;
- an alkynyl radical;
- a hydroxyl radical;
- a hydroxyalkyl radical;
- an alkoxy radical;
- an alkoxyalkyl radical;
- an alkylcarbonyl radical;
- a hydroxyalkoxyalkyl radical;
- an amino radical;
- a monoalkylamino radical;
- a dialkylamino;
- an aminoalkyl radical;
- an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals;
- a hydroxyl radical;
- a aminoalkyl radical;
- a carboxyl radical;
- a carboxyalkyl radical;
- a carbamoyl radical;
- a carbamoylalkyl radical;
- an alkoxycarbonyl radical;
- a monoalkylaminocarbonyl radical;
- a dialkylaminocarbonyl radical;
- a monoalkylaminocarbonylalkyl radical;
- and
- a dialkylaminocarbonylalkyl radical;
- R4 is chosen from
- an alkyl radical;
- an alkenyl radical;
- an alkynyl radical;
- a hydroxyalkyl radical;
- an alkoxyalkyl radical;
- an alkylcarbonyl radical;
- a hydroxyalkoxyalkyl radical;
- an aminoalkyl radical;
- an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals;
- a hydroxyl radical;
- a aminoalkyl radical;
- a carboxyl radical;
- a carboxyalkyl radical;
- a carbamoyl radical;
- a carbamoylalkyl radical;
- an alkoxycarbonyl radical;
- a monoalkylaminocarbonyl radical;
- a dialkylaminocarbonyl radical;
- a monoalkylaminocarbonylalkyl radical;
- and
- a dialkylaminocarbonylalkyl radical.
54 more elements
A process for the oxidation dyeing of keratin fibers, comprising applying a dye composition to the fibers in the presence of at least one oxidizing agent, for a time sufficient to develop a desired coloration, wherein the dye composition comprises, as an oxidation base, at least one compound of formula (I), and the addition salts thereof
- wherein:
- a ranges from 0 to 4, it being understood that when a is greater than or equal to 2, then the radicals R1 may be identical or different,
- b ranges from 0 to 4, it being understood that when b is greater than or equal to 2, then the radicals R4 may be identical or different,
- c is equal to 0 or 1,
- R1 is chosen from halogen atoms;
- C1-C8 aliphatic and alicyclic, saturated and unsaturated hydrocarbon-based chains, wherein at least one carbon atom is optionally replaced with at least one entity chosen from oxygen, nitrogen, silicon, and sulphur atoms and an SO2 group;
- and an onium radical Z;
- with the proviso that the radical R1 does not comprise a peroxide bond or diazo, nitro or nitroso radicals,
- R2 comprises an onium radical Z, wherein an onium radical is a nitrogen-based quaternary radical,
- R3 is chosen from
- an alkyl radical;
- an alkenyl radical;
- an alkynyl radical;
- a hydroxyl radical;
- a hydroxyalkyl radical;
- an alkoxy radical;
- an alkoxyalkyl radical;
- an alkylcarbonyl radical;
- a hydroxyalkoxyalkyl radical;
- an amino radical;
- a monoalkylamino radical;
- a dialkylamino;
- an aminoalkyl radical;
- an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals;
- a hydroxyl radical;
- a aminoalkyl radical;
- a carboxyl radical;
- a carboxyalkyl radical;
- a carbamoyl radical;
- a carbamoylalkyl radical;
- an alkoxycarbonyl radical;
- a monoalkylaminocarbonyl radical;
- a dialkylaminocarbonyl radical;
- a monoalkylaminocarbonylalkyl radical;
- and
- a dialkylaminocarbonylalkyl radical;
- R4 is chosen from
- an alkyl radical;
- an alkenyl radical;
- an alkynyl radical;
- a hydroxyalkyl radical;
- an alkoxyalkyl radical;
- an alkylcarbonyl radical;
- a hydroxyalkoxyalkyl radical;
- an aminoalkyl radical;
- an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals;
- a hydroxyl radical;
- a aminoalkyl radical;
- a carboxyl radical;
- a carboxyalkyl radical;
- a carbamoyl radical;
- a carbamoylalkyl radical;
- an alkoxycarbonyl radical;
- a monoalkylaminocarbonyl radical;
- a dialkylaminocarbonyl radical;
- a monoalkylaminocarbonylalkyl radical;
- and
- a dialkylaminocarbonylalkyl radical.
55 more elements
A multi-compartment kit, wherein at least one first compartment comprises a dye composition comprising, as an oxidation base, at least one compound of formula (I), and the addition salts thereof
- wherein:
- a ranges from 0 to 4, it being understood that when a is greater than or equal to 2, then the radicals R1 may be identical or different,
- b ranges from 0 to 4, it being understood that when b is greater than or equal to 2, then the radicals R4 may be identical or different,
- c is equal to 0 or 1,
- R1 is chosen from halogen atoms;
- C1-C8 aliphatic and alicyclic, saturated and unsaturated hydrocarbon-based chains, wherein at least one carbon atom is optionally replaced with at least one entity chosen from oxygen, nitrogen, silicon, and sulphur atoms and an SO2 group;
- and an onium radical Z;
- with the proviso that the radical R1 does not comprise a peroxide bond or diazo, nitro or nitroso radicals,
- R2 comprises an onium radical Z, wherein an onium radical is a nitrogen-based quaternary radical,
- R3 is chosen from
- an alkyl radical;
- an alkenyl radical;
- an alkynyl radical;
- a hydroxyl radical;
- a hydroxyalkyl radical;
- an alkoxy radical;
- an alkoxyalkyl radical;
- an alkylcarbonyl radical;
- a hydroxyalkoxyalkyl radical;
- an amino radical;
- a monoalkylamino radical;
- a dialkylamino;
- an aminoalkyl radical;
- an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals;
- a hydroxyl radical;
- a aminoalkyl radical;
- a carboxyl radical;
- a carboxyalkyl radical;
- a carbamoyl radical;
- a carbamoylalkyl radical;
- an alkoxycarbonyl radical;
- a monoalkylaminocarbonyl radical;
- a dialkylaminocarbonyl radical;
- a monoalkylaminocarbonylalkyl radical;
- and
- a dialkylaminocarbonylalkyl radical;
- R4 is chosen from
- an alkyl radical;
- an alkenyl radical;
- an alkynyl radical;
- a hydroxyalkyl radical;
- an alkoxyalkyl radical;
- an alkylcarbonyl radical;
- a hydroxyalkoxyalkyl radical;
- an aminoalkyl radical;
- an aminoalkyl radical wherein the amine is monosubstituted or disubstituted with at least one radical chosen from alkyl, acetyl and hydroxyalkyl radicals;
- a hydroxyl radical;
- a aminoalkyl radical;
- a carboxyl radical;
- a carboxyalkyl radical;
- a carbamoyl radical;
- a carbamoylalkyl radical;
- an alkoxycarbonyl radical;
- a monoalkylaminocarbonyl radical;
- a dialkylaminocarbonyl radical;
- a monoalkylaminocarbonylalkyl radical;
- and
- a dialkylaminocarbonylalkyl radical and at least one second compartment comprises at least one oxidizing agent.
55 more elements
Dependencies are inferred from the claim text.