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US 2002/0165368 A1Published application
Novel azo compounds, use in dyeing, compositions containing them and dyeing processes
AssigneeL'oreal
InventorsJean-Christophe Henrion, Michel Philippe
Life of this patent
Estimating the term…
Abstract
Azo compounds of the 2-(4-amino)phenyldiazinecarboximidamide type and 2-(4-amino)phenylhydrazinecarboximidamide type, a process for their synthesis, their use for dyeing keratin fibers, dye compositions containing them, and dyeing processes.
Claims48
An azo compound of formula (I) or the acid addition salt thereof:
- 7
- in which:
- R1 and R2, independently of each other, represent a hydrogen atom;
- a C1-C6 alkyl radical;
- a 5- or 6-membered cycloalkyl radical;
- a 5- or 6-membered aromatic ring;
- a 5- or 6-membered aromatic ring substituted with a C1-C6 alkyl radical, a halogen atom, an amino radical, a hydroxyl radical, or a C1-C6 alkoxy radical;
- or R1 and R2 form, together with the nitrogen atom to which they are attached, a 4- to 8-membered heterocycle, said heterocycle containing one or more hetero atoms chosen from sulfur, nitrogen and oxygen;
- R3 and R4, independently of each other, represent a hydrogen atom, a C1-C6 alkyl radical, a C1-C6 monohydroxyalkyl radical or a C2-C6 polyhydroxyalkyl radical;
- and
- A is a 5- to 6-membered aromatic ring which can be interrupted by one or more hetero atoms chosen from sulfur, nitrogen and oxygen, or fused to another 5- to 6-membered aromatic ring.
8 more elements
A method for dyeing keratin fibers comprising the step of contacting said fibers, for a time sufficient to achieve said dyeing, with a compound of formula (II) or the acid addition salt thereof:
- 8
- in which:
- R1 and R2, independently of each other, represent a hydrogen atom;
- a C1-C6 alkyl radical;
- a 5- or 6-membered cycloalkyl radical;
- a 5- or 6-membered aromatic ring;
- a 5- or 6-membered aromatic ring substituted with a C1-C6 alkyl radical, a halogen atom, an amino radical, a hydroxyl radical, or a C1-C6 alkoxy radical;
- or R1 and R2 form, together with the nitrogen atom to which they are attached, a 4- to 8-membered heterocycle, said heterocycle containing one or more hetero atoms chosen from sulfur, nitrogen and oxygen;
- R3 and R4, independently of each other, represent a hydrogen atom, a C1-C6 alkyl radical, a C1-C6 monohydroxyalkyl radical or a C2-C6 polyhydroxyalkyl radical;
- and
- A is a 5- to 6-membered aromatic ring which can be interrupted by one or more hetero atoms chosen from sulfur, nitrogen and oxygen, or fused to another 5- to 6-membered aromatic ring.
8 more elements
A method for making a compound of formula (I) or the acid addition salt thereof comprising the steps of:
- (a) carrying out a reduction reaction in a solvent medium on a compound of formula (III) below
- 9
- in which
- R1 and R2, independently of each other, represent a hydrogen atom;
- a C1-C6 alkyl radical;
- a 5- or 6-membered cycloalkyl radical;
- a 5- or 6-membered aromatic ring;
- a 5- or 6-membered aromatic ring substituted with a C1-C6 alkyl radical, a halogen atom, an amino radical, a hydroxyl radical, or a C1-C6 alkoxy radical;
- or R1 and R2 form, together with the nitrogen atom to which they are attached, a 4- to 8-membered heterocycle, said heterocycle containing one or more hetero atoms chosen from sulfur, nitrogen and oxygen;
- A is a 5- to 6-membered aromatic ring which can be interrupted by one or more hetero atoms chosen from sulfur, nitrogen and oxygen, or fused to another 5- to 6-membered aromatic ring;
- for a time sufficient to give a compound of formula (II) or the acid addition salt thereof:
- 10
- in which:
- R1 and R2, independently of each other, represent a hydrogen atom;
- a C1-C6 alkyl radical;
- a 5- or 6-membered cycloalkyl radical;
- a 5- or 6-membered aromatic ring;
- a 5- or 6-membered aromatic ring substituted with a C1-C6 alkyl radical, a halogen atom, an amino radical, a hydroxyl radical, or a C1-C6 alkoxy radical, or R1 and R2 form, together with the nitrogen atom to which they are attached, a 4- to 8-membered heterocycle, said heterocycle containing one or more hetero atoms chosen from sulfur, nitrogen and oxygen;
- R3 and R4, independently of each other, represent a hydrogen atom, a C1-C6 alkyl radical, a C1-C6 monohydroxyalkyl radical or a C2-C6 polyhydroxyalkyl radical;
- and
- A is a 5- to 6-membered aromatic ring which can be interrupted by one or more hetero atoms chosen from sulfur, nitrogen and oxygen, or fused to another 5- to 6-membered aromatic ring;
- and
- (b) oxidizing the compound of formula (II) in a solvent for a time sufficient to give the compound of formula (I) or an acid addition salt thereof:
- 11
- in which:
- R1 and R2, independently of each other, represent a hydrogen atom;
- a C1-C6 alkyl radical;
- a 5- or 6-membered cycloalkyl radical;
- a 5- or 6-membered aromatic ring;
- a 5- or 6-membered aromatic ring substituted with a C1-C6 alkyl radical, a halogen atom, an amino radical, a hydroxyl radical, or a C1-C6 alkoxy radical;
- or R1 and R2 form, together with the nitrogen atom to which they are attached, a 4- to 8-membered heterocycle, said heterocycle containing one or more hetero atoms chosen from sulfur, nitrogen and oxygen;
- R3 and R4, independently of each other, represent a hydrogen atom, a C1-C6 alkyl radical, a C1-C6 monohydroxyalkyl radical or a C2-C6 polyhydroxyalkyl radical;
- and
- A is a 5- to 6-membered aromatic ring which can be interrupted by one or more hetero atoms chosen from sulfur, nitrogen and oxygen, or fused to another 5- to 6-membered aromatic ring.
31 more elements
The compound of formula (II′) or an acid addition salt thereof:
- 12
- in which
- R1 and R2, independently of each other, represent a hydrogen atom;
- a C1-C6 alkyl radical;
- a 5- or 6-membered cycloalkyl radical;
- a 5- or 6-membered aromatic ring;
- a 5- or 6-membered aromatic ring substituted with a C1-C6 alkyl radical, a halogen atom, an amino radical, a hydroxyl radical, or a C1-C6 alkoxy radical;
- or R1 and R2 form, together with the nitrogen atom to which they are attached, a 4- to 8-membered heterocycle, said heterocycle containing one or more hetero atoms chosen from sulfur, nitrogen and oxygen;
- R3 and R4, independently of each other, represent a hydrogen atom, a C1-C6 alkyl radical, a C1-C6 monohydroxyalkyl radical or a C2-C6 polyhydroxyalkyl radical;
- and
- A is a 5- to 6-membered aromatic ring which can be interrupted by one or more hetero atoms chosen from sulfur, nitrogen and oxygen, or fused to another 5- to 6-membered aromatic ring,
- with the proviso that at least one of the radicals R1, R2, R3 and R4 is other than a hydrogen atom.
9 more elements
A composition for dyeing keratin fibers, wherein said composition comprises, in a medium which is suitable for dyeing, at least one compound chosen from compounds of formula (I) and salts thereof:
- 13
- in which:
- R1 and R2, independently of each other, represent a hydrogen atom;
- a C1-C6 alkyl radical;
- a 5- or 6-membered cycloalkyl radical;
- a 5- or 6-membered aromatic ring;
- a 5- or 6-membered aromatic ring substituted with a C1-C6 alkyl radical, a halogen atom, an amino radical, a hydroxyl radical, or a C1-C6 alkoxy radical;
- or R1 and R2 form, together with the nitrogen atom to which they are attached, a 4- to 8-membered heterocycle, said heterocycle containing one or more hetero atoms chosen from sulfur, nitrogen and oxygen;
- R3 and R4, independently of each other, represent a hydrogen atom, a C1-C6 alkyl radical, a C1-C6 monohydroxyalkyl radical or a C2-C6 polyhydroxyalkyl radical;
- and
- A is a 5- to 6-membered aromatic ring which can be interrupted by one or more hetero atoms chosen from sulfur, nitrogen and oxygen, or fused to another 5- to 6-membered aromatic ring and compounds of formula (II) and salts thereof:
- 14
- in which:
- R1 and R2, independently of each other, represent a hydrogen atom;
- a C1-C6 alkyl radical;
- a 5- or 6-membered cycloalkyl radical;
- a 5- or 6-membered aromatic ring;
- a 5- or 6-membered aromatic ring substituted with a C1-C6 alkyl radical, a halogen atom, an amino radical, a hydroxyl radical, or a C1-C6 alkoxy radical;
- or R1 and R2 form, together with the nitrogen atom to which they are attached, a 4- to 8-membered heterocycle, said heterocycle containing one or more hetero atoms chosen from sulfur, nitrogen and oxygen;
- R3 and R4, independently of each other, represent a hydrogen atom, a C1-C6 alkyl radical, a C1-C6 monohydroxyalkyl radical or a C2-C6 polyhydroxyalkyl radical;
- and
- A is a 5- to 6-membered aromatic ring which can be interrupted by one or more hetero atoms chosen from sulfur, nitrogen and oxygen, or fused to another 5- to 6-membered aromatic ring.
19 more elements
The composition of claim 21 wherein said human keratin fibers are hair.
A multi-compartment dyeing device or kit for dyeing keratin fibers, comprising at least two compartments, wherein
- a first compartment contains composition (A) comprising, in a medium which is suitable for dyeing, at least one compound of formula (II) or the acid addition salt thereof:
- 15
- in which:
- R1 and R2, independently of each other, represent a hydrogen atom;
- a C1-C6 alkyl radical;
- a 5- or 6-membered cycloalkyl radical;
- a 5- or 6-membered aromatic ring;
- a 5- or 6-membered aromatic ring substituted with a C1-C6 alkyl radical, a halogen atom, an amino radical, a hydroxyl radical, or a C1-C6 alkoxy radical;
- or R1 and R2 form, together with the nitrogen atom to which they are attached, a 4- to 8-membered heterocycle, said heterocycle containing one or more hetero atoms chosen from sulfur, nitrogen and oxygen;
- R3 and R4, independently of each other, represent a hydrogen atom, a C1-C6 alkyl radical, a C1-C6 monohydroxyalkyl radical or a C2-C6 polyhydroxyalkyl radical;
- and
- A is a 5- to 6-membered aromatic ring which can be interrupted by one or more hetero atoms chosen from sulfur, nitrogen and oxygen, or fused to another 5- to 6-membered aromatic ring, and
- a second compartment contains composition (B) containing, in a medium which is suitable for dyeing, at least one oxidizing agent.
10 more elements
Dependencies are inferred from the claim text.