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Composition for dyeing keratin fibers, comprising at least one diamino-n,n-dihydropyrazolone derivative, at least one coupler, and at least one heterocyclic direct dye

A technology of keratin fiber and composition, applied in the field of dyeing, can solve the problem of not being able to obtain color and luster, and achieve the effect of good tolerance

Active Publication Date: 2011-11-16
LOREAL SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Application of oxidative chromogenic bases such as p-phenylenediamine and p-aminophenol derivatives can obtain a fairly wide range of colors at alkaline pH. At the same time as the excellent performance in terms of fastness, the color with excellent chroma cannot be obtained

Method used

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  • Composition for dyeing keratin fibers, comprising at least one diamino-n,n-dihydropyrazolone derivative, at least one coupler, and at least one heterocyclic direct dye
  • Composition for dyeing keratin fibers, comprising at least one diamino-n,n-dihydropyrazolone derivative, at least one coupler, and at least one heterocyclic direct dye
  • Composition for dyeing keratin fibers, comprising at least one diamino-n,n-dihydropyrazolone derivative, at least one coupler, and at least one heterocyclic direct dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0339] Example 1: Synthesis of 2,3-diamino-6,7-dihydro-1H, 5H-pyrazolo[1,2-a]pyrazol-1-one dihydrochloride 5

[0340]

[0341] - Step 1: Synthesis of 3-(3,5-dibromo-4-nitro-1H-pyrazol-1-yl)propan-1-ol 1

[0342] In a 500 ml three-necked flask, 0.369 mol of sodium acetate is introduced into a solution of 0.184 mol of dibromonitropyrazole in 250 ml of N-methylpyrrolidone, and the reaction medium is then heated to 80°C.

[0343] At this temperature, 0.369 mol of 3-bromopropanol was added dropwise. And maintain this temperature for 5 hours.

[0344] After cooling to room temperature, the reaction medium is poured onto ice while stirring.

[0345] 3-(3,5-Dibromo-4-nitro-1H-pyrazol-1-yl)propan-1-ol 1 was precipitated out. It was filtered off with suction and dried to give a yield of 75%.

[0346] Detection of expected compound C by mass spectrometry 6 h 7 Br 2 N 3 o 3 the quality of.

[0347] NMR analysis ( 1 H 400 MHz and 13 C 100.61 MHz DMSO d 6 ) is consistent ...

Embodiment 2

[0382] Example 2: Synthesis of 2-amino-3-(ethylamino)-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one dihydrochloride 9

[0383]

[0384] - Step 2: Synthesis of 3-[3-bromo-5-(ethylamino)-4-nitro-1H-pyrazol-1-yl]propan1-ol 6.

[0385] In a three-necked flask, 15 mmol of 3-(3,5-dibromo-4-nitro-1H-pyrazol-1-yl)propan-1-ol was stirred into 30 ml of ethanol. The homogeneous medium obtained is heated to 75° C., and then 93 mmol of ethylamine are added dropwise, while stirring is maintained for 4 hours.

[0386] After cooling to room temperature, the medium was poured onto ice and 3-[3-bromo-5-(ethylamino)-4-nitro-1H-pyrazol-1-yl]propan-1-ol 6 was precipitated.

[0387] The yellow solid is filtered off with suction and washed well with water and diisopropyl ether. at P 2 o 5 Dry under vacuum. The mass of product obtained was 3.6 g.

[0388] NMR analysis ( 1 H 400MHz and 13 C 100.61MHz DMSOd 6 ) is consistent with the expected structure.

[0389] Detection of expected ...

Embodiment 3

[0409] Example 3: 2-amino-3-(isopropylamino)-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one 13

[0410]

[0411] - Step 2: 3-[3-Bromo-5-(isopropylamino)-4-nitro-1H-pyrazol-1-yl]propan-1-ol 10

[0412] In a three-necked flask, 15 mmol of 3-[3,5-dibromo-4-nitro-1H-pyrazol-1-yl]propan-1-ol was stirred into 30 ml of ethanol. The resulting homogeneous medium is heated to 75° C., and then 93 mmol of isopropylamine are added dropwise, while maintaining stirring, over a period of 4 hours.

[0413] After cooling to room temperature, the medium was poured onto ice and neutralized with hydrochloric acid. 3-[3-Bromo5-(isopropylamino)-4-nitro-1H-pyrazol-1-yl]propan-1-ol 10 was extracted with dichloromethane.

[0414] The organic phase was dried over sodium sulfate and evaporated to remove the solvent under reduced pressure to obtain 4.37 g of 3-[3-bromo-5-(isopropylamino)-4-nitro-1H-pyrazol-1-yl]prop-1 -alcohol 10.

[0415] NMR analysis ( 1 H 400MHz and 13 C 100.61MHz DMSO d ...

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Abstract

Disclose herein is a composition for dyeing keratin fibers, for example, human keratin fibers such as the hair, comprising at least one oxidation base chosen from diamino-N,N-dihydropyrazolones and addition salts thereof, at least one coupler, and at least one heterocyclic direct dye. Also disclosed herein is a method for dyeing keratin fibers comprising applying a composition of the present disclosure to the keratin fibers. The compositions and methods of the present disclosure may make it possible to obtain fast coloration of keratin fibers that is resistant to light and / or to washing.

Description

technical field [0001] The present invention relates to a composition for dyeing keratin fibers, especially human keratin fibers such as hair, comprising at least one dihydropyrazolone type or its additives. Salt-forming oxidation bases, at least one coupler and at least one heterocyclic direct dye, and also to a dyeing process using the aforementioned composition. Background technique [0002] It is known to dye keratinous fibers, especially human keratin fibers such as hair, using dyeing compositions which contain oxidation dye precursors, especially o- or p-phenylenediamine, o- or p- Aminophenols, and heterocyclic compounds commonly known as oxidation bases such as diaminopyrazole derivatives, pyrazolo[1,5-a]-pyrimidine derivatives, pyrimidine derivatives, pyridine derivatives, indole derivatives compounds and indoline derivatives. Oxidation dye precursors or oxidation bases are colorless or light-coloured compounds which, when combined with oxidation products, can prod...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K8/49A61Q5/10
CPCA61K8/492A61K8/494A61K2800/4324A61Q5/10A61K8/4926A61K8/49
Inventor L·赫尔库埃
Owner LOREAL SA
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