Hair coloring compositions

Details Hair coloring compositions Hair coloring compositions

2002-04-05

2004-08-10

Mruk, Brian P. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S428000, C008S432000, C008S493000, C008S587000, C008S618000

Reexamination Certificate

active

06773464

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to hair colouring compositions and methods of colouring hair using the compositions.
BACKGROUND OF THE INVENTION
The cosmetic colouring of hair has been known for many years. Colourants are typically classified as being temporary or permanent. In temporary colouring, the colour can be washed from the hair relatively easily. So-called permanent colouring of hair typically involves the formation of oligomeric or polymeric compounds in and/or on the hair fibre. However, the colouring is not truly permanent in the strict sense of the word because the colourants can still be washed from the hair over longer periods of time.
Therefore, there remains a need for hair colourants which are more resistant to being washed off the hair.
It is known that hair fibres contain certain enzymes in and/or on the fibre. For example, the enzyme transglutaminase has been found to be present in hair fibres. Transglutaminase catalyses the formation of covalent bonds between specific peptide-bound glutamine resides and various primary amino groups of peptide-bound lysines or polyamines, acting as aminic donor substrates.
Transglutaminase can be utilised to attach agents to body tissues, as described in WO99/36570. In the specific systems exemplified in this document, exogenous transgutaminase is used to attach polylysine or polyglutamine to skin or hair. In the only specific example of a system for application to hair, a mousse for thickening hair is described which contains a mucopolysaccharide linked to polyglutamine.
Transglutaminase substrates have been involved in the treatment of hair loss. For example, FR-A-2740331 describes cosmetic compositions for the treatment of hair which contain one or more esters of butyric acid and, optionally, a substrate for transglutaminase.
The use of exogenous transglutaminase in a cosmetic composition for forming a protective layer on the hair, skin or nails, is described in U.S. Pat. No. 5,525,336. The ingredients of the composition cross-link with the outer layer of skin, hair or nails to form the layer.
WO00/64405 describes the use of substrates for a variety of endogenous enzymes that are present in hair fibres, for the delivery of hair benefit agents to the hair. Transglutaminase is one of the endogenous enzymes mentioned in the document.
The present invention is based on the finding of specific systems for colouring hair which may involve the action of endogenous transglutaminase. The systems have the advantage in that the colourant may be covalently bound to the hair fibre and, therefore, more resistant to being removed by washing.
SUMMARY OF THE INVENTION
According to a first aspect of the present invention, there is provided a hair colouring composition or kit of parts comprising: a compound which is capable of acting as a substrate for endogenous transglutaminase in and/or on hair and which comprises a chromophore that is capable of absorbing and/or emitting light in the visible part of the electromagnetic spectrum; and a reducing agent.
In a second aspect, the invention provides a method of colouring hair which comprises treating the hair with a composition according to the first aspect of the invention.
DETAILED DESCRIPTION
The present invention is based on the finding of particularly effective compositions for colouring hair. The compositions contain a compound which can act as a substrate for transglutaminase and a reducing agent. The compound preferably forms a covalent bond to the hair by the action of the endogenous transglutaminase in and/or on the hair.
Compound which is Capable of Acting as a Substrate for Endogenous Transglutaminase
The compound which is capable of acting as a substrate for endogenous transglutaminase in and/or on hair and which comprises a chromophore that is capable of absorbing and/or emitting light in the visible part of the electromagnetic spectrum (also referred to herein as the compound) preferably comprises an amino group covalently bonded to the chromophore.
In a preferred embodiment, the compound comprises a group of formula NH
2
covalently bonded to the chromophore by a linker group of formula (CH
2
)
n
, wherein n is an integer from 1 to 12, more preferably from 1 to 6, most preferably from 3 to 5. Optionally, the linker group can contain one or more other atoms in the (CH
2
)
n
chain, such as, for example, O. These compounds are known to be suitable as substrates for transglutaminase. The precise nature of the linker group is not critical, provided that the compound can act as a substrate for transglutaminase. Suitable methods for attaching the amino group to the chromophore via the linker group are well-known in the art. Alternatively, the compound may be synthesised or otherwise obtained with the amino and linker groups already present in the chromophore. The compound may contain one or more than one amino group and/or more than one chromophore.
The compound may be present in the compositions of the invention in solution. Preferably, the solution will be aqueous, containing as solvent from 50 to 100% water. However, other cosmetically acceptable solvents and/or diluents may be present in the solution such as, for example, ethanol and/or other lower alcohols. When the compound is present in solution, it will typically be present in the composition at a concentration of from
0.0001M to 0.01M, although the concentration may fall outside this range and will depend on the product form of the composition.
The nature of the chromophore in the compound can vary widely, provided that, when the compound is bonded to the hair, the hair is coloured by the compound. Therefore, the chromophore can be inorganic (ie, metal ion based) or organic. Preferably, however, the chromophore in the compound is an organic dye. Suitable organic dyes are well-known in the art and may comprise a plurality of ring systems, at least some of which are aromatic, and one or more groups bearing a positive or negative charge.
Although the dye may impart any colour to the hair, the compounds of the invention have been found to be particularly effective at colouring the hair red. A suitable chromophore for colouring the hair red is Texas Red, a commercially available organic dye, although other chromophores may be used instead. Permanent red colouration of hair is difficult to achieve using conventional hair colouring techniques.
The compositions of the invention many comprise a single compound or a mixture of different compounds, for example having the same or different light absorbing and/or emitting properties
The Reducing Agent
The compositions of the invention comprise a reducing agent. The reducing agent preferably comprises one or more thiol (SH) groups. Compounds containing thiol groups are known in other applications to be cosmetically acceptable for application to the hair.
Suitable reducing agents include, for example, compounds containing from 1 to 6 carbon atoms and one or more other functional groups such as hydroxyl and carboxylate, eg, dithiothreitol, thioglycolate and mixtures thereof.
A non-exausitive list of reducing agents is as follows: Mercapto-carboxylic Acids (e.g. 2-mercaptopropionic acid, 3-mercaptopropionic acid, mercaptosuccinic acid, thioglycolic acid, ammonium thioglycollate, sodium thioglycollate, L-cysteine, Di-mercapto-adipic acid); Mercapto-amines (e.g. L-cysteine ethyl ester, L-cysteine methyl ester, N-acetyl-L-cysteine, cysteamine); Mercapto-amides (e.g. thioglycolamide, N-hydroxyethyl mercapto-acetamide, N-methyl mercapto acetamide, 2-mercapto-propionamide); Sulphites (e.g. ammonium bisulphite, sodium bisulphite, ammonium sulphite, sodium sulphite); hydroxides (e.g. guanidine hydroxide, sodium hydroxide); Alcohols and Diols (e.g. resorcinol, thioglycerol, glycerol monothioglycollate, glycol thioglycolate); Di-thio compounds (e.g. dihydrolipoic acid, sodium dihydrolipoate, dithiothreitol, 1,3-dithiopropanol); Others (e.g. lithium chloride, tris(hydroxymethyl)phosphine, cuprammonium hydroxide, thioglycolic hydrazide, 2-mercapto-ethanesulphonic acid, homocysteine thiol

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