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Symmetrical diazo compounds, compositions comprising them, method of coloring, and device

A diazo compound, symmetrical technique, applied in the direction of chemical apparatus and methods, apparatus for washing hair or scalp, azo dyes, etc.

Inactive Publication Date: 2007-01-10
LOREAL SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

While these compounds represent an advance in the state of the art, there is still room for improvement in their staining results

Method used

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  • Symmetrical diazo compounds, compositions comprising them, method of coloring, and device
  • Symmetrical diazo compounds, compositions comprising them, method of coloring, and device
  • Symmetrical diazo compounds, compositions comprising them, method of coloring, and device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0409] 1- Synthesis of Compounds:

[0410] Synthesis of Compound 2

[0411]

[0412] Compound 1 (1.477 g, n=0.002 mol) was reacted in 20 ml of isopropanol at 100° C. for 8 hours in the presence of 1.08 g (n=0.02 mol) of p-phenylenediamine. Concentration of the reaction mixture gave a purple residue. Purification by liquid chromatography was required and pure compound 2 was obtained as a purple powder.

[0413] 1 H NMR and mass analysis were consistent with the expected compound.

[0414] Synthesis of compound 5

[0415]

[0416] Compound 3 is obtained by reacting the diazonium salt of p-chloroaniline in the presence of imidazole.

[0417] step 1

[0418] Compound 3 (2.03 g) was reacted in 30 ml of dimethylformamide at 100° C. for 8 hours in the presence of 0.78 ml of 1,6-dibromohexane and 0.69 g of potassium carbonate. The reaction mixture was cooled to ambient temperature. Precipitation from ethyl acetate gave a red precipitate. Vacuum filtration, washing with ...

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Abstract

The present disclosure relates to symmetrical cationic diazo compounds of formula (I) below, their resonance forms, and also their acid addition salts and their solvates: wherein W1 radicals, which are identical, are chosen from a halogen atom, or an-NR4-Ph-NR5R6, -NR4-Ph-OR7. -O-Ph-OR, or -O-Ph-NR5R6 group or else an -NR5R6 or -OR7 group with certain provisos;L, a non-cationic linker connecting the two identical azo chromophores, is chosen from a covalent bond; an optionally substituted C1-C40 alkyl radical optionally interrupted by a (hetero)cycle. the alkyl radical being optionally interrupted by at least one heteroatom or group comprising at least one heteroatom or an optionally substituted phenyl radical. The disclosure further relates to dyeing compositions comprising such compounds as a direct dye in a medium appropriate for the dyeing of keratin fibers, and also to a method of coloring keratin fibers that employs this composition, and a device comprising a plurality of compartments.

Description

technical field [0001] The present invention relates to symmetrical cationic diazonium compounds comprising a 2-imidazolium base and a non-cationic linking group, dyeing compositions comprising said compounds as direct dyes in a medium suitable for dyeing keratin fibres, dyeing agents using said compositions Method for dyeing keratin fibers, and device with multiple compartments. Background technique [0002] The practical application of dyeing keratin fibers, and in particular human keratin fibers such as hair, with dyeing compositions comprising direct dyes is known. These compounds are colored or dyed molecules that have an affinity for fibers. For example, the practice of using direct fuels of the nitrobenzene type, anthraquinone dyes, nitropyridines and dyes of the azo, xanthene, acridine, azine or triarylmethane type is known. [0003] These dyes are usually applied to the fibers, optionally in the presence of an oxidizing agent, if at the same time the fibers are de...

Claims

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Application Information

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IPC IPC(8): C07D233/88C07D233/54C07D403/14C07D401/14C07D471/06C09B44/12A45D19/00A61K8/49A61Q5/10
CPCC07D403/12A61Q5/10C09B55/008C09B44/16C07D471/04A61K8/4946C07D233/88C07D403/06C07D403/14
Inventor H·戴维A·格里夫斯N·多布雷斯
Owner LOREAL SA
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