Colouring agents with enzymes

Details Colouring agents with enzymes Colouring agents with enzymes

2001-08-22

2003-10-07

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

C008S406000, C008S407000, C008S411000, C008S412000, C008S421000, C424S094100, C424S094400

Reexamination Certificate

active

06630003

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to compositions containing a special enzyme system for coloring keratin fibers, to their use and to corresponding processes for coloring keratin fibers.
BACKGROUND OF THE INVENTION
By virtue of their intensive colors and good fastness properties, so-called oxidation colorants play a prominent role in the coloring of keratin fibers, particularly human hair. Oxidation colorants contain oxidation dye precursors, so-called primary intermediates and secondary intermediates. The primary intermediates form the actual dyes with one another or by coupling with one or more secondary intermediates in the presence of oxidizing agents or atmospheric oxygen.
In general, natural-looking hair colors cannot be obtained solely with a primary intermediate or with a special primary intermediate/secondary intermediate combination. In practice, therefore, combinations of various primary intermediates and/or secondary intermediates are normally used.
The primary intermediates normally used are primary aromatic amines containing another free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and derivatives thereof.
Special representatives are, for example, p-phenylenediamine, p-toluylenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 2-(2,5-diaminophenyl)-ethanol, 2-(2,5-diaminophenoxy)-ethanol, 1-phenyl-3-carboxyamido4-amino-5-pyrazolone, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triamino-4-hydroxypyrimidine and 1,3-N,N′-bis-(2′-hydroxyethyl)-N,N′-bis-(4′-aminophenyl)-diamino-2-propanol.
The secondary intermediates used are generally m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols. Particularly suitable secondary intermediates are 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-methyl-5-pyrazolone, 2,4-dichloro-3-aminophenol, 1,3-bis-(2,4-diaminophenoxy)-propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenoll, 2-methyl resorcinol, 5-methyl resorcinol and 2-methyl-4-chloro-5-aminophenol.
In principle, the color can be oxidatively developed with atmospheric oxygen. However, a chemical oxidizing agent is preferably used. Suitable oxidizing agents are persulfates, chlorites and, above all, hydrogen peroxide or addition products thereof with urea, melamine and sodium borate. A 2-9% aqueous hydrogen peroxide solution is normally used. The keratin fibers can be damaged by such high concentrations of oxidizing agent, particularly where they have already been “permed” or bleached. In some cases, skin irritation can also be caused by these high concentrations.
A significant start to solving this problem is to reduce the concentration of oxidizing agent. Accordingly, attempts have already been made on the one hand to find dye precursors which, by virtue of their chemical structure, can be oxidized even by relatively small quantities of hydrogen peroxide or by atmospheric oxygen. On the other hand, it has been proposed to use enzymes as biocatalysts which are capable of catalyzing the desired oxidation process with very little, if any, hydrogen peroxide simply in the presence of atmospheric oxygen.
DE-OS 2 155 390 describes an enzyme-activated oxidative hair coloring process in which small quantities of H
2
O
2
are used in combination with a peroxidase enzyme. EP-A1-0 310 675 also discloses enzymatic hair treatment preparations which contain at least one dielectron-reducing oxidase that uses oxygen as acceptor. EP-B1 0 548 620 describes enzymatic hair colorants where oxidation of the dye precursors is catalyzed by the use of a peroxidase. Finally, EP-A2 0 795 313 describes enzymatic hair colorants which contain an oxygen-oxidoreductase/substrate system and a peroxidase and, as a compulsory secondary intermediate, an m-phenylenediamine derivative. However, none of these colorants has yet proved totally convincing in terms of their coloring performance (intensity, tone, brilliance, fastness properties).
Readily oxidizable dye precursors have the disadvantage, along with the enzymatic color development hitherto described, that the results they give in regard to intensity, brilliance and color fastness properties are poorer by comparison with the conventional processes.
Accordingly, the problem addressed by the present invention was to provide colorants for keratin fibers which would enable the fibers to be treated without damage and at the same time would guarantee excellent coloring performance.
It has now surprisingly been found that high-performance colorants with distinct advantages in terms of fiber and skin care are obtained if they contain at least one dye precursor, a choline-based oxidase system and at least one peroxidase.
DETAILED DESCRIPTION OF THE INVENTION
Keratin fibers in the context of the invention are understood to be pelts, wool, feathers and in particular human hair.
According to the invention, a choline-based oxidase system is understood to be choline oxidase in combination with choline as substrate. Choline is oxidized by choline oxidase in accordance with the following reaction scheme:
For the purposes of the present invention, choline is preferably used in the form of a salt with a physiologically compatible organic or inorganic acid. Examples of such salts are the chloride, the bromide, the iodide, the citrate, the hydrogen tartrate, the hydrogen carbonate, the methyl sulfate and the p-toluenesulfonate. Choline chloride is particularly preferred.
Choline oxidase (EC 1.1.3.17) can be obtained from various sources. One occurrence was found, for example, in human cells. Choline oxidase produced by Alcaligenes species and
Arthrobacter globiformis
is particularly preferred for the purposes of the invention. Choline oxidases are commercially available and are marketed, for example, by Sigma. According to the invention, the activity of the choline oxidase is defined as follows: one unit [1 U] of choline oxidase catalyzes the oxidation of 1 &mgr;mol of choline to betaine aldehyde in one minute at pH 8.0/37° C., 1 &mgr;mol of H
2
O
2
being formed (according to Sigma's definition of the commercial products).
Choline oxidase is used in the compositions according to the invention in quantities of 1 to 50,000 U per 100 g of coloring preparation. Quantities of 1 to 10,000 U per 100 g of coloring preparation are preferred, the range from 400 to 5,000 U per 100 g of coloring preparation being most particularly preferred.
According to the invention, the substrate choline is used in quantities of 1 to 5% by weight, based on the coloring preparation as a whole.
Besides the choline-based oxidase system, the compositions according to the invention also contain a peroxidase (EC 1.11.1.7). The peroxidases may be obtained from animals, plants or fungi. Vegetable peroxidases and fungus-based peroxidase can be particularly preferred for the purposes of the invention, soybean peroxidase being most particularly preferred.
In another embodiment of the present invention, peroxidases with a minimal catalase content, for example horse radish peroxidase, are preferably used.
According to the invention, the activity of the peroxidase is defined as follows: 1 unit [1 U] of peroxidase forms 1.0 mg of purpurogallin from pyrogallol in 20 seconds at pH 6.0/20° C. (according to Sigma's definition of the commercial products).
According to the invention, the peroxidase is used in a quantity of 1 to 100,000 U. Quantities of 1 to 10,000 U are preferred, a quantity of 1 to 500 U being most particularly preferred. The quantities mentioned are all based on 100 g of coloring preparation.
The compositions according to the inven

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