Use of flavylium type compounds non-substituted in position...

Details Use of flavylium type compounds non-substituted in position... Use of flavylium type compounds non-substituted in position...

1999-08-20

2001-06-05

Liott, Caroline D. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S405000, C008S424000, C008S579000, C008S657000, C008S659000

Reexamination Certificate

active

06241785

ABSTRACT:

The invention relates to the use of flavylium-type compounds non-substituted in position 3, and substituted by at least one hydroxyl or alkoxy radical, and in particular Apigenidin, as colouring agents, in or for the manufacture of compositions for dyeing keratinous fibres, in particular human keratinous fibres such as hair.
Many compounds containing a flavylium ring (F):
constitute the basic structure of natural colouring agents which are responsible for most of the red, blue or purple colours of flowers or fruits worldwide, and which are commonly known as “anthocyanins” or alternatively “anthocyanidins”, in the case of the aglycone form of anthocyanins.
The majority of anthocyanins and anthocyanidins contain, respectively, a glycoside or hydroxyl radical in position 3 of the flavylium ring.
These anthocyanins and anthocyanidins were previously widely used as natural colouring agents for dyeing textiles. Their use for this application was then abandoned because of the lack of fastness of the colours obtained to light and to washing.
It is well known, see in this respect patent U.S. Pat. No. 3,266,903, that the instability to light of these natural colouring agents is dependent on the nature of the substituent in position 3 of the flavylium ring. When position 3 of the flavylium ring is occupied by a sugar, as is the case for anthocyanins, or by a hydroxyl radical, as is the case for their aglycone form, the anthocyanidins, the colours are unstable. Thus, in the food industry, it has been recommended to prevent the decolorization, caused by light, of compositions containing these anthocyanin and anthocyanidin colouring agents which are not very stable, by photostabilizing them by combining with flavonols (EP-24 731 A1), or with ascorbic acid derivatives (U.S. Pat. No. 4,208,434).
Moreover, in the field of hair dyeing, direct dyes are being sought which, without supplying an oxidizing agent, are capable of modifying by themselves the natural shade of hair, temporarily.
In this application, the colouring agents must satisfy a number of criteria: be as harmless as possible, that is to say exhibit acceptable innocuousness and generate reproducible colours which are sufficiently resistant, in particular, to light, washing and adverse weather conditions.
In addition, these colouring agents, as is well known, are used in the form of mixtures, in order to obtain natural shades.
However, in this field, the so-called natural colouring agents such as Henna generate only a range of shades close to blond. To broaden the pallet of colours, it is necessary to find other natural colouring agents whose shades are similar to the basic colours and which, when mixed in particular with Henna, can meet the expectations of consumers.
It is after major research studies carried out on this subject that the Applicant has now discovered, completely unexpectedly and surprisingly, flavylium-type compounds non-substituted in position 3 and substituted by at least one hydroxyl or alkoxy radical, which make it possible to dye intensely, and without oxidizing agent, keratinous fibres, and in particular human keratinous fibres such as hair, in shades which are particularly stable to light and to shampooing.
It has been observed, in addition, that the hair dyes resulting from the use of these compounds preserved the condition of the hair, were reproducible and exhibited excellent innocuousness.
This discovery forms the basis of the present invention.
The subject of the present invention is thus the use of flavylium-type compounds non-substituted in position 3, and substituted by at least one hydroxyl or alkoxy radical, in pure form or in the form of plant extracts containing them, as colouring agents, in or for the preparation of a composition for dyeing keratinous fibres, in particular cosmetic compositions for the direct dyeing of human keratinous fibres such as hair.
Among these flavylium-type compounds, there are preferably used the compounds substituted in position 4′ by a hydroxyl, alkoxy or hydroxyalkyl radical, in pure form or in the form of plant extracts containing them.
There are still more particularly used the flavylium-type compounds as described above and of the following formula (I):
in which formula (I):
R
1
denotes an OH radical or a saturated or unsaturated, linear or branched C
1
-C
8
alkoxy radical,
R
2
, R
3
and R
4
, which are identical or different, denote H or R
1
, it being understood that at least one of the radicals R
1
to R
4
denotes OH,
X is an anion preferably denoting a halogen or a radical:
in which R
5
and R
6
are saturated or unsaturated, linear or branched C
1
-C
8
alkyl radicals, in pure form or in the form of plant extracts containing them.
Another subject of the invention is a composition for dyeing keratinous fibres, in particular a cosmetic composition for the direct dyeing of human keratinous fibres such as hair, comprising, in a medium appropriate for dyeing, at least one flavylium-type compound non-substituted in position 3 and substituted by at least one hydroxy or alkoxy radical, and such as those defined above, in a pure form or in the form of a plant extract containing it.
Its subject is also the methods of dyeing using these compositions.
However, other characteristics, features and advantages of the invention will appear even more clearly on reading the description which follows, as well as the various concrete, but not at all limiting, examples intended to illustrate it.
For the purposes of the invention, keratinous fibres are mainly understood to mean natural textile fibres such as wool, human keratinous fibres such as in particular hair, body hair, eyelashes and eyebrows. The invention relates more particularly to hair.
The compounds of formula (I) which are particularly preferred according to the present invention are chosen from the group of those for which, in formula (I), R
1
denotes OH or OCH
3
.
There may be mentioned in particular among them the chlorides of the following compounds:
4′,5,7-trihydroxyflavylium, commonly called “Apigenidin chloride”,
3′,4′,7-trihydroxyflavylium,
4′-hydroxyflavylium,
4′,7-dihydroxyflavylium,
3′,4′-dihydroxyflavylium,
3′,4′-dihydroxy-7-methoxyflavylium.
Among these compounds, Apigenidin chloride (4′,5,7-trihydroxyflavylium) and 3′,4′,7-trihydroxyflavylium chloride are even more particularly preferred.
A specific form of the invention consists in using Apigenidin chloride in the form of a plant extract which can easily be prepared by extraction and isolated from
Sorghum caudatum
leaves, as has, for example, been described and prepared by the authors Kouda-Bonafos, Czyzewska, Nacro and Oehlschlager in Journal of Chemical Ecology-1994-Vol. 20, No. 8-pages 2123-2125.
It can also be extracted from the stems, seeds or leaves of
Sorghum bicolore
, from the petals of
Gesneria fulgens
, as well as from the species
Blechum, Procerum
and
Sorgho
contaminated by
Colletotrichum graminicola.
A plant extract of
Sorghum caudatum
having a titre approximately greater than 70% by weight of apigenidin chloride is particularly preferred according to the present invention.
The flavylium-type compounds non-substituted in position 3 and substituted by at least one hydroxyl or alkoxy radical according to the invention can be easily obtained by the synthesis route, and at a low cost, especially by the well-known method of R. Robinson and D. D. Pratt [(J., Chem. Soc., 745 (1923)]. The said method involves condensing an ortho-hydroxybenzaldehyde or its substitution derivatives with acetophenone or its substitution derivatives in order to obtain, by choosing the substituents, the desired compounds of formula (I).
By taking as an example Apigenidin chloride (4′,5,7-trihydroxyflavylium chloride), the synthesis scheme (i) may be the following:
By taking as an example 3′,4′,7-trihydroxyflavylium chloride, the synthesis scheme (ii) may be the following:
Various synthesis routes, well-known in the prior art, lead to Apigenidin.

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