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Use of azomethine compounds carrying two pyrazolopyridine units for dyeing keratin fibers

A pyrazolopyridine, azomethine technology, applied in disazomethine dyes, cosmetics, organic chemistry and other directions, can solve the problems of poor relative durability, low resistance to photochemical erosion, weak dyeing power and the like

Active Publication Date: 2020-04-17
LOREAL SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The coloration resulting from the use of direct dyes is often chromatic, but however only temporary or semi-permanent, because of the nature of the interaction that binds these direct dyes to the keratin fibers, and their separation from the fibers. Desorption of the surface and / or core contributes to their weak stain power and their poor relative permanence to washing or perspiration
These direct dyes are also often light sensitive due to the low resistance of the chromophore to photochemical attack, causing the coloring of the hair to fade over time

Method used

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  • Use of azomethine compounds carrying two pyrazolopyridine units for dyeing keratin fibers
  • Use of azomethine compounds carrying two pyrazolopyridine units for dyeing keratin fibers
  • Use of azomethine compounds carrying two pyrazolopyridine units for dyeing keratin fibers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0199] Example 1 : Synthesis of a dye with the formula:

[0200]

[0201]

[0202] Put 500ml of ethanol into a 1-liter single-neck round bottom flask equipped with a calcium chloride protection tube, then add 50g (0.2177mol) of 2-[(3-aminopyrazolo[1,5-a ]pyridin-2-yl)oxy]ethanol hydrochloride.

[0203] To this solution was added 14.2 g (0.986 mol) of 2-chloropyridine-3,5-diamine and 60.3 ml (0.346 mol) of N-ethyl-N-(propan-2-yl)propan-2-amine .

[0204] The solution thus obtained was stirred at room temperature for 4 days. The black precipitate formed was isolated by filtration, washed with water, and dried in a desiccator under vacuum at 30° C. in the presence of a desiccant to constant weight. A black solid is thus obtained.

[0205] Spectral analysis indicated that the obtained compound corresponded to the above structure.

Embodiment 2

[0206] Example 2 : 3,3-[(5-amino-3-iminopyridine-2,6-(1H,3H)-diylidene)bis(nitrilopyrazolo[1,5-a]pyridine-3, 2-diyloxy group)] the synthesis of dipropan-1-ol hydrochloride:

[0207]

[0208] Put 150ml of ethanol into a 500ml single-neck round bottom flask equipped with a calcium chloride protection tube, then add 10.4g (0.04268mol) of 3-[(3-aminopyrazolo[1,5-a ]pyridin-2-yl)oxy]propan-1-ol hydrochloride.

[0209] To this solution was added 2.78 g (0.01940 mol) of 2-chloropyridine-3,5-diamine and 11.8 ml (0.06790 mol) of N-ethyl-N-(propan-2-yl)propan-2-amine .

[0210] The solution thus obtained was then stirred at room temperature for 4 days. The black precipitate formed was isolated by filtration, washed with water, and dried in a desiccator under vacuum at 30° C. in the presence of a desiccant to constant weight. A solid is thus obtained in the form of a black powder.

[0211] Spectral analysis showed that the obtained compound corresponds to 3,3'-[(5-amino-3-imino...

Embodiment 3

[0212] Example 3 : N,N'-(5-amino-3-iminopyridine-2,6-(1H,3H)-diylidene)bis{2-[2-(dimethylamino)ethoxy]pyrazole Synthesis of [1,5-a]pyridin-3-amine} dihydrochloride:

[0213]

[0214] Put 550ml of ethanol into a 1-liter single-necked round-bottomed flask equipped with a calcium chloride protection tube, then add 55g (0.1876mol) of 2-[2-(dimethylamino)ethoxy]pyridine under stirring Azolo[1,5-a]pyridin-3-amine dihydrochloride.

[0215] To this solution were added 12.24 g (0.085 mol) of 2-chloropyridine-3,5-diamine and 52 ml (0.346 mol) of N-ethyl-N-(propan-2-yl)propan-2-amine.

[0216] The solution thus obtained was stirred at room temperature for 4 days. The viscous black oil obtained after removal of the solvent by evaporation under vacuum was chromatographed on a silica column in normal phase with the eluent consisting of 50% dichloromethane and 50% methanol.

[0217] After removal of the solvent by evaporation under vacuum, the viscous black oil crystallized as a blac...

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Abstract

The invention relates to a compound chosen from the compounds of formulae (I) and (II), the leucoforms thereof, the optical and geometrical isomers thereof and the tautomers thereof, and also the addition salts thereof with an acid or a base, and the solvates thereof. The invention also relates to the use of these particular compounds for dyeing keratin fibres.

Description

technical field [0001] The present invention relates to novel compounds of the azomethine class carrying two pyrazolopyridine units and to their use for dyeing keratin fibers, and in particular human keratin fibers such as hair. Background technique [0002] It is known practice to dye keratin fibers with dye compositions containing direct dyes. These compounds are colored and colored molecules that have an affinity for fibers. It is known practice to use, for example, direct dyes of the nitrobenzene class, anthraquinone or nitropyridine dyes, and dyes of the azo, xanthene, acridine, azine or triarylmethane class. [0003] These dyes are often applied to the fibers optionally in the presence of an oxidizing agent if it is desired to obtain a simultaneous brightening of the fibers. Once the dwell time has elapsed, the fibers are rinsed, optionally washed and dried. [0004] The coloration resulting from the use of direct dyes is often chromatic, but however only temporary ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09B69/10A61Q5/06
CPCA61Q5/065C07D471/04C09B69/107A61K8/494A61Q5/10C09B55/006
Inventor 阿齐兹·法德利斯特凡娜·布莱
Owner LOREAL SA
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