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2, 5-diaminopyridine oxidation color display alkali for dyeing keratin fiber

A technology for oxidizing chromogenic bases and diaminopyridines, which can be used in cosmetics, organic chemistry, cosmetic preparations, etc., and can solve problems such as unstable light exposure.

Inactive Publication Date: 2006-04-12
LOREAL SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These compositions produce high intensity green tints but are not stable to light

Method used

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  • 2, 5-diaminopyridine oxidation color display alkali for dyeing keratin fiber
  • 2, 5-diaminopyridine oxidation color display alkali for dyeing keratin fiber
  • 2, 5-diaminopyridine oxidation color display alkali for dyeing keratin fiber

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0643] Example 1. Synthesis of 2-methoxy-6-(pyrrolidin-1-yl)-3-aminopyridine trihydrochloride

[0644]

[0645] 1. Synthesis of 2-methoxy-3-nitro-6-(pyrrolidin-1-yl)pyridine

[0646] Add 4.79g (0.021mol) of 6-chloro-2-methoxy-3-nitropyridine, 40ml of ethanol and 3.5ml (0.042mol) of pyrrolidine into a fully equipped round bottom flask, and reflux under stirring The mixture was cooled to room temperature for 1 hour, and the crystalline product was filtered off, washed with diisopropyl ether, and dried to obtain 4.6 g of a yellow powder, yield: 96%.

[0647]The results of mass spectrometry and NMR spectroscopic analysis were consistent with the pre-conceived structure.

[0648] 2. Synthesis of 2-methoxy-6-(pyrrolidin-1-yl)-3-aminopyridine trihydrochloride

[0649] 4 g (0.0179 mol) of 2-methoxy-3-nitro-6-(pyrrolidin-1-yl)pyridine synthesized above, 200 ml of ethanol and 0.8 g of palladium on carbon were charged into a 300 ml autoclave. The reduction mixture was stirred for 2...

example 2

[0651] Example 2.1-(5-amino-6-methoxypyridin-2-yl)pyrrolidin-3-ol dihydrochloride

[0652]

[0653] 1. Synthesis of 1-(6-methoxy-5-nitropyridin-2-yl)pyrrolidin-3-ol

[0654] Add 2 g (0.0106 mol) of 6-chloro-2-methoxy-3-nitropyridine, 25 ml of ethanol and 1.9 g of 3-pyrrolidinol into a fully equipped round bottom flask, and stir the mixture at 50°C for 1 hours, the mixture was poured into ice water with stirring. The formed precipitate was filtered and dried to obtain 2 g of a yellow powder.

[0655] The results of mass spectrometry and NMR spectroscopic analysis were consistent with the pre-conceived structure.

[0656] 2. Synthesis of 1-(5-amino-6-methoxypyridin-2-yl)pyrrolidin-3-ol dihydrochloride

[0657] 2g (8.5mmol) 1-(6-methoxy-5-nitropyridin-2-yl) pyrrolidin-3-alcohol, 100ml ethanol and 0.5g palladium on charcoal join in the autoclave of 300ml, in The reduction reaction was carried out with stirring for 1 hour at a pressure of 8 bar. The catalyst was then remove...

example 3

[0659] Example 3.3-Amino-2-methoxy-6-(morpholin-4-yl)pyridine dihydrochloride

[0660]

[0661] 1.4-(6-methoxy-5-nitropyridin-2-yl)morpholine

[0662] 4g (0.02mol) of 6-chloro-2-methoxy-3-nitropyridine, 60ml ethanol and 3.69ml morpholine were added in a fully equipped round bottom flask, and the mixture was refluxed for 2 hours under stirring, The mixture was then poured into ice water with stirring, the formed precipitate was filtered and dried to give 2.2 g of yellow powder, yield = 50%.

[0663] The results of mass spectrometry and NMR spectroscopic analysis were consistent with the pre-conceived structure.

[0664] 2. Synthesis of 3-amino-2-methoxy-6-(morpholin-4-yl)pyridine dihydrochloride

[0665] 2g (0.01mol) of 4-(6-methoxy-5-nitropyridin-2-yl) morpholine, 100ml of ethanol and 0.5g of palladium on charcoal were added to the 300ml autoclave at 8 The reduction reaction was carried out with stirring for 1 hour under a pressure of bar. The catalyst was then removed ...

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PUM

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Abstract

This invention relates to dyeing compositions for the dyeing of keratin fibres comprising at least one oxidation base of the 2,5-diaminopyridine type, the use of the compositions for the dyeing of keratin fibres and a dyeing processes employing the compositions. Another object of the invention is to provide novel 2,5-diaminopyridine compounds for dyeing oxidation bases.

Description

field of invention [0001] One of the objects of the present invention is to provide a dyeing composition used for dyeing keratin fibers, which contains a 2,5-diaminopyridine-type oxidation base; the application also relates to the dyeing composition The use of the compound in the dyeing of keratin fibers and the method of dyeing with the composition; Another object of the present invention is to provide a class of novel 2,5-diaminopyridine compounds as oxidation bases. Background technique [0002] It is known to color keratin fibers, especially human, with dyeing compositions containing precursors of oxidative dyes, usually called oxidation bases (e.g. o- or p-phenylenediamines, o- or p-aminophenols and heterocyclic compounds). Colored hair. These colorless or faintly colored oxidation bases are combined with oxidizing substances to produce colored compounds through an oxidative chromogenic process. [0003] It is also known that the shades obtained from these oxidation b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K8/49A61Q5/10C07D401/12A61K8/00A61K8/20A61K8/22A61K8/31A61K8/33A61K8/34A61K8/40A61K8/41A61K8/66C07D213/74C07D401/04
CPCC07D213/74A61K8/347A61Q5/10C07D401/04A61K8/415A61K8/4926A61K8/49
Inventor L·维达尔A·法利
Owner LOREAL SA