U.S. patent application number 09/467896 was filed with the patent office on 2002-02-14 for use of hydroxystilbenes for dyeing, ready-to-use composition containing them and dyeing process.
Invention is credited to Bernard, Bruno, Pruche, Francis, Saint Leger, Didier.
Application Number | 20020016998 09/467896 |
Document ID | / |
Family ID | 9534341 |
Filed Date | 2002-02-14 |
United States Patent
Application |
20020016998 |
Kind Code |
A1 |
Pruche, Francis ; et
al. |
February 14, 2002 |
USE OF HYDROXYSTILBENES FOR DYEING, READY-TO-USE COMPOSITION
CONTAINING THEM AND DYEING PROCESS
Abstract
The invention relates to the use of hydroxystilbenes for dyeing,
to ready-to-use dye compositions comprising them, to a dyeing
process using them and to a multi-compartment device containing the
compositions used in the processes of the invention.
Inventors: |
Pruche, Francis; (Paris,
FR) ; Saint Leger, Didier; (Courbevoie, FR) ;
Bernard, Bruno; (Neuilly-Sur-Seine, FR) |
Correspondence
Address: |
NIXON & VANDERHYE PC
8TH FLOOR
1100 NORTH GLEBE ROAD
ARLINGTON
VA
22201
|
Family ID: |
9534341 |
Appl. No.: |
09/467896 |
Filed: |
December 21, 1999 |
Current U.S.
Class: |
8/401 |
Current CPC
Class: |
A61Q 5/10 20130101; A61K
8/347 20130101 |
Class at
Publication: |
8/401 |
International
Class: |
C09B 067/00 |
Foreign Application Data
Date |
Code |
Application Number |
Dec 22, 1998 |
FR |
9816258 |
Claims
1. Use, for dyeing, of hydroxystilbene of formula (I) below: 2in
which: n denotes an integer from 2 to 4, n' denotes an integer from
0 to 4, R.sub.1, and R.sub.2, which may be identical or different,
denote a hydrogen atom, a halogen atom or an alkyl, alkoxy,
carboxyl or acyl radical; R.sub.3 and R.sub.4, which may be
identical or different, denote a hydrogen atom, a halogen atom or
an alkyl, alkoxy, carboxyl or acyl radical; Z and Z', which may be
identical or different, represent a hydrogen atom or a glycosyl
radical; or one of the addition salts thereof with an acid.
2. Use according to claim 1, for dyeing keratin substances.
3. Use according to claim 1 or 2, characterized in that R.sub.1,
and R.sub.2 denote a hydrogen atom and R.sub.3 and R.sub.4, which
may be identical or different, denote a hydrogen atom or a
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 alkoxy or carboxyl
radical.
4. Use according to any one of claims 1 to 3, characterized in that
the hydroxystilbenes of formula (I) are chosen from the following
compounds: 4'-methoxy-3,3',5-stilbenetriol 3-glucoside,
trans-1-(3'-carboxy-4'-hydro-
xyphenyl)-2-(2",5"-dihydroxyphenyl)ethane,
3,5-dihydroxy-4'-methoxystilben- e 3-O-beta-D-glucoside,
trans-3,4',5-trihydroxystilbene, 4',5-dihydroxystilbene
3-O-beta-D-glucoside, 3,3',4,5'-tetrahydroxystilbe- ne,
3,5-dihydroxy-4'-bromostilbene, 2,3,5,4'-tetrahydroxystilbene
2-O-beta-D-glucoside, and 3,5,3'-trihydroxy-4'-methoxystilbene
5-O-beta-D-glucoside; or one of the addition salts thereof with an
acid.
5. Use according to any one of claims 1 to 4, characterized in that
the addition salts with an acid are chosen from the hydrochlorides,
hydrobromides, sulphates, citrates, succinates, tartrates, lactates
and acetates.
6. Ready-to-use dye composition, characterized in that it
comprises, in a medium which is suitable for dyeing, at least one
compound of formula (I) as defined in any one of claims 1 to 5 and
at least one oxidizing agent.
7. Composition according to claim 6, characterized in that the
oxidizing agent is chosen from enzymes, hydrogen peroxide, urea
peroxide, persalts and peracids, metal salts, quinones and
nitrites.
8. Composition according to claim 7, characterized in that the
enzymes are chosen from pyranose oxidases, glucose oxidases,
glycerol oxidases, lactate oxidases, pyruvate oxidases, uricases,
choline oxidases, laccases, sarcosine oxidases, bilirubin oxidases,
tyrosinases, peroxidases and catalases, or from plant or animal
extracts containing the abovementioned enzymes, optionally in the
presence of a donor (or substrate) required for the functioning of
the said enzymes.
9. Composition according to claim 8, characterized in that the
enzyme corresponds to tyrosinase.
10. Composition according to any one of claims 6 to 9,
characterized in that the compound(s) of formula (I) represent(s)
from 0.01 to 10% by weight relative to the total weight of the
ready-to-use dye composition.
11. Composition according to claim 10, characterized in that the
compound(s) of formula (I) represent(s) from 0.1 to 5% by weight
relative to the total weight of the ready-to-use dye
composition.
12. Composition according to any one of claims 6 to 11,
characterized in that the oxidizing agent represents from 0.001 to
25% by weight relative to the total weight of the ready-to-use dye
composition.
13. Composition according to claim 12, characterized in that the
oxidizing agent represents from 0.1 to 10% by weight relative to
the total weight of the ready-to-use dye composition.
14. Composition according to any one of claims 6 to 13,
characterized in that it contains one or more oxidation bases other
than the compounds of formula (I) and/or one or more couplers.
15. Composition according to claim 14, characterized in that the
oxidation base(s) represent(s) from 0.0005 to 12% by weight
relative to the total weight of the ready-to-use dye composition
and in that the coupler(s) represent(s) from 0.0001 to 10% by
weight relative to the total weight of the ready-to-use dye
composition.
16. Composition according to claim 15, characterized in that the
oxidation base(s) represent(s) from 0.005 to 8% by weight relative
to the total weight of the dye composition, and in that the
coupler(s) represent(s) from 0.005 to 8% by weight relative to the
total weight of the dye composition.
17. Composition according to any one of claims 6 to 16,
characterized in that it also contains direct and/or self-oxidizing
dyes chosen from azo dyes, anthraquinone dyes and nitro derivatives
of the benzene series.
18. Composition according to any one of claims 6 to 17,
characterized in that the medium which is suitable for dyeing
consists of water or a mixture of water and at least one organic
solvent.
19. Composition according to any one of claims 6 to 18,
characterized in that it has a pH of between 3 and 12.
20. Composition according to any one of claims 6 to 19,
characterized in that it also contains surfactants, polymers,
inorganic or organic thickeners, antioxidants, penetrating agents,
sequestering agents, fragrances, buffers, dispersants or
conditioning agents.
21. Composition according to any one of claims 9 to 20,
characterized in that it also contains L-tyrosine; a pyrimidine
3-oxide derivative substituted in position 6; L-DOPA; dopamine;
peptides with L-tyrosine, L-DOPA and/or dopamine residues; caffeic
acid; coumaric acid; chlorogenic acid; elagic acid; catechins; OPCs
or plant or animal extracts containing these abovementioned
compounds.
22. Dye composition according to any one of claims 6 to 21,
characterized in that it is in the form of liquids, creams or gels
or in any other form which is suitable for carrying out a dyeing
operation.
23. Dyeing process, characterized in that at least one dye
composition as defined according to any one of claims 6 to 22 is
applied to a support for a period which is sufficient to develop
the desired coloration.
24. Process according to claim 23, characterized in that it
comprises a preliminary step which consists in separately storing,
on the one hand, a composition (A) comprising, in a medium which is
suitable for dyeing, at least one compound of formula (I) as
defined in any one of claims 1 to 5, and, on the other hand, a
composition (B) containing, in a medium which is suitable for
dyeing, at least one oxidizing agent as defined in any one of
claims 7 to 9, and then in mixing them together at the time of use,
after which this mixture is applied to the support.
25. Multi-compartment dyeing device or "kit", characterized in that
it comprises a first compartment containing composition (A) as
defined in claim 24, and a second compartment containing
composition (B) as defined in claim 24.
Description
[0001] The present invention relates to the use of
hydroxystilbenes, to ready-to-use dye compositions containing them,
to dyeing processes using them and to a multi-compartment device
used for carrying out the said dyeing processes.
[0002] It is well known to use so-called "oxidation" dyes in
compositions for dyeing the hair. These dyes have the advantage of
leading to shades which give better coverage and which are faster
than those obtained using so-called "direct" dyes. Nevertheless,
the oxidation dyes currently used have the drawback of not being
entirely harmless and thus entail potential risks of allergies.
[0003] The Applicant has investigated oxidation dyes which do not
have these drawbacks and which give the hair a coloration with
satisfactory resistance to light, washing, bad weather,
perspiration and various treatments to which the hair may be
subjected. Furthermore, oxidizing dyes are also sought which can be
used in the context of enzymatic colorations and which can thus
make it possible to avoid the use of oxidizing agents such as
hydrogen peroxide, which can be the cause of substantial
degradation of keratin fibres.
[0004] Japanese patent application No. 64-38009 describes the use
of hydroxystilbenes as tyrosinase inhibitors and discloses
depigmenting compositions containing hydroxystilbenes.
[0005] The Applicant has just discovered, and this forms the
subject of the invention, that the use of hydroxystilbenes as
oxidation dye precursors in dye compositions makes it possible to
obtain a wide range of colorations, the said colorations having
particularly noteworthy resistance to light, washing, bad weather
and perspiration.
[0006] One subject of the invention is thus the use of
hydroxystilbene for dyeing, and particularly for dyeing keratin
substances.
[0007] Another subject of the invention consists of ready-to-use
dye compositions containing at least one hydroxystilbene and an
oxidizing agent.
[0008] Another subject of the invention also relates to a process
for dyeing a support, and in particular keratin substances, using
such compositions.
[0009] Another subject of the invention relates to a
multi-compartment dyeing device or kit containing the various
compounds used for the dyeing operations according to the invention
for dyeing.
[0010] An essential subject of the present invention is thus the
use of hydroxystilbene of formula (I) below: 1
[0011] in which:
[0012] n denotes an integer from 2 to 4,
[0013] n' denotes an integer from 0 to 4,
[0014] R.sub.1 and R.sub.2, which may be identical or different,
denote a hydrogen atom, a halogen atom or an alkyl, alkoxy,
carboxyl or acyl radical;
[0015] R.sub.3 and R.sub.4, which may be identical or different,
denote a hydrogen atom, a halogen atom or an alkyl, alkoxy,
carboxyl or acyl radical;
[0016] Z and Z', which may be identical or different, represent a
hydrogen atom or a glycosyl radical; or one of the addition salts
thereof with an acid.
[0017] In formula (I) above, the alkyl, alkoxy or acyl radicals may
be linear or branched.
[0018] The alkyl groups in particular denote groups of 1 to 20
carbon atoms such as, for example, ethyl, methyl, propyl,
isopropyl, n-propyl, butyl, n-butyl, tert-butyl, pentyl, n-pentyl,
isopentyl, n-hexyl, isohexyl, octyl, nonyl, decyl, undecyl and
pentadecyl groups. Preferably, these alkyl groups denote a group of
1 to 6 carbon atoms.
[0019] The alkoxy groups denote groups --O--R, R representing an
alkyl group as defined above.
[0020] The acyl groups denote groups --COR, R representing an alkyl
group as defined above.
[0021] The glycosyl radical represents a radical derived from a
glycose, i.e. a monosaccharide or simple sugar, such as arabinose,
glucose or fructose. The glycosyl radical preferably denotes a
glucosyl radical.
[0022] The hydroxystilbenes of formula (I) can be used for dyeing
supports of very varied nature, such as cotton, cellulose,
plastics, etc. Specifically, it has been found that the use of
these dye precursors makes it possible to obtain dyes which have a
strong affinity for their support.
[0023] In one preferred embodiment of the invention, the
hydroxystilbenes are used for dyeing keratin substances such as the
skin or keratin fibres such as the hair or the nails.
[0024] In one preferred embodiment of the invention, the compounds
of formula (I) are chosen from those for which R.sub.1, and R.sub.2
denote a hydrogen atom and R.sub.3 and R.sub.4, which may be
identical or different, denote a hydrogen atom or a C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 alkoxy or carboxyl radical.
[0025] Even more preferably, the hydroxystilbenes of formula (I)
are chosen from the following compounds:
[0026] 4'-methoxy-3,3',5-stilbenetriol 3-glucoside or
rhapontin,
[0027]
trans-1-(3'-carboxy-4'-hydroxyphenyl)-2-(2',5'-dihydroxyphenyl)etha-
ne,
[0028] 3,5-dihydroxy-4'-methoxystilbene 3-O-beta-D-glucoside or
deoxyrhapontin,
[0029] trans-3,4',5-trihydroxystilbene or resveratrol,
[0030] 4',5-dihydroxystilbene 3-O-beta-D-glucoside,
[0031] 3,3',4,5'-tetrahydroxystilbene or picestannol,
[0032] 3,5-dihydroxy-4'-bromostilbene,
[0033] 2,3,5,4'-tetrahydroxystilbene 2-O-beta-D-glucoside, and
[0034] 3,5,3'-trihydroxy-4'-methoxystilbene
5-O-beta-D-glucoside;
[0035] or one of the addition salts thereof with an acid.
[0036] In the context of the present invention, the addition salts
with an acid are chosen in particular from the hydrochlorides,
hydrobromides, sulphates, citrates, succinates, tartrates, lactates
and acetates.
[0037] Another subject of the invention relates to ready-to-use dye
compositions comprising, in a medium which is suitable for dyeing,
at least one compound of formula (I) as defined above and at least
one oxidizing agent.
[0038] The oxidizing agent may be chosen in particular from
enzymes, hydrogen peroxide, urea peroxide, persalts and peracids,
metal salts such as, for example, copper salts, quinones and
nitrites.
[0039] The enzymes can be chosen in particular from pyranose
oxidases, glucose oxidases, glycerol oxidases, lactate oxidases,
pyruvate oxidases, uricases, choline oxidases, sarcosine oxidases,
bilirubin oxidases, laccases, tyrosinases, peroxidases and
catalases, or from plant or animal extracts containing the
abovementioned enzymes, optionally in the presence of a donor (or
substrate) required for the functioning of the said enzymes.
[0040] When the enzymes are used as oxidizing agents, and in
particular tyrosinase, the ready-to-use dye compositions of the
invention can thus also contain L-tyrosine; pyrimidine 3-oxide
derivatives substituted in position 6, in particular those
described in FR 96/11316, L-DOPA; dopamine; peptides with
L-tyrosine, L-DOPA and/or dopamine residues; caffeic acid; coumaric
acid; chlorogenic acid; elagic acid; catechins; OPCs or plant or
animal extracts containing these abovementioned compounds.
[0041] The enzymes used according to the invention can be of
animal, microbiological (bacterial, fungal or viral) or synthetic
(obtained by chemical or biotechnological synthesis) origin.
[0042] The enzyme(s) can be used in pure crystalline form or in
diluted form in a diluent which is inert with respect to the said
enzyme.
[0043] Examples of uricases which may be mentioned in particular
are uricase extracted from boar liver, uricase from Arthrobacter
globiformis and uricase from Aspergillus flavus.
[0044] Examples of sources of choline oxidase which may be
mentioned in particular are rat liver, bacteria such as
Arthrobacter globiformis, Achromobacter cholinophagum or
Alcaligenes, and fungi such as Cylindrocarpon didynum.
[0045] Examples of sources of sarcosine oxidase which may be
mentioned in particular are bacteria such as Arthrobacter and in
particular Arthrobacter ureafaciens and Arthrobacter globiformis,
Streptomyces, Bacillus, Pseudomonas, Corynebacterium or Alcaligenes
such as, for example, Alcaligenes denitrificans, and fungi such as
Cylindrocarpon didynum.
[0046] Examples of sources of bilirubin oxidase which may be
mentioned in particular are intestinal mucosa and rat liver, and
bacteria such as Myrothecium verucania, Myrothecium cinctum and
Myrothecium roridum.
[0047] Among the laccases of plant origin which can be used
according to the invention, mention may be made of the laccases
produced by plants which synthesize chlorophyll, such as those
indicated in patent application FR-A-2,694,018.
[0048] Mention may be made in particular of the laccases extracted
from Anacardiacea plants, from Podocarpacea plants, from Rosmarinus
off., from Solanum tuberosum, from Iris sp., from Coffea sp., from
Daucus carrota, from Vinca minor, from Persea americana, from
Catharenthus roseus, from Musa sp., from Malus pumila, from Gingko
biloba and from Monotropa hypopithys (Indian pine).
[0049] Among the laccases of microbial (in particular fungal)
origin, or obtained by biotechnology, which can be used according
to the invention, mention may be made of the laccases from
Polyporus versicolor, from Rhizoctonia praticola and from Rhus
vernicifera, as described, for example, in patent applications
FR-A-2,112,549 and EP-A-504,005; the laccases described in patent
applications WO95/07988, WO95/33836, WO95/33837, WO96/00290,
WO97/19998 and WO97/19999, the content of which forms an integral
part of the present description, such as, for example, the laccases
of Scytalidium, of Polyporus pinsitus, of Myceliophthora
thermophila, of Rhizoctonia solani, of Pyricularia oryzae and
variants thereof.
[0050] Laccases of microbial origin or those obtained by
biotechnology will be chosen more preferably.
[0051] In one particularly preferred embodiment of the invention,
the enzyme used corresponds to tyrosinase. In the present
invention, the term "tyrosinase" should be understood as meaning
any enzyme with tyrosinase activity, it being possible for this
enzyme to have other enzymatic activities. Tyrosinase activity can
be defined as the enzymatic activity which catalyses the oxidation
of tyrosinase to lead to the formation of the melanin precursor:
dopaquinone.
[0052] Examples of sources of tyrosinase which may be mentioned in
particular are potato, mushrooms, microorganisms such as Neurospora
crassa, etc.
[0053] In the ready-to-use compositions according to the invention,
the compound(s) of formula (I) represent(s) from 0.01 to 10% by
weight relative to the total weight of the ready-to-use dye
composition and preferably from 0.1 to 5% by weight relative to the
total weight of the ready-to-use dye composition.
[0054] The oxidizing agent itself can represent from 0.001 to 25%
by weight relative to the total weight of the ready-to-use dye
composition and preferably from 0.1 to 10% by weight relative to
the total weight of the ready-to-use dye composition.
[0055] The ready-to-use dye composition in accordance with the
invention can also contain one or more oxidation dye precursors
other than those of formula (I), i.e. one or more oxidation bases
and/or one or more couplers.
[0056] When they are present, the oxidation base(s) preferably
represent(s) from 0.0005 to 12% by weight approximately relative to
the total weight of the ready-to-use dye composition in accordance
with the invention and even more preferably from 0.005 to 8% by
weight approximately relative to this weight.
[0057] When they are present, the coupler(s) preferably
represent(s) from 0.0001 to 10% by weight approximately relative to
the total weight of the ready-to-use dye composition and even more
preferably from 0.005 to 8% by weight approximately relative to
this weight.
[0058] The ready-to-use dye composition according to the invention
can also contain one or more direct dyes which can be chosen in
particular from azo dyes, anthraquinone dyes and nitro derivatives
of the benzene series, in particular to modify the shades or to
enrich them with glints.
[0059] When the compositions of the invention are used for dyeing
the skin, they can also contain DHA.
[0060] The medium which is suitable for dyeing generally consists
of water or a mixture of water and at least one organic solvent to
dissolve the compounds which would not be sufficiently soluble in
water.
[0061] The solvents can be present in proportions preferably of
between 1 and 40% by weight approximately relative to the total
weight of the dye composition and even more preferably between 5
and 30% by weight approximately.
[0062] The pH of the ready-to-use compositions of the invention may
be adapted as a function of the oxidizing agent used and such that
the dyeing properties of the composition are not adversely
affected. The pH values will, in particular, have to be adapted so
as not to denature the enzymes when they are used as oxidizing
agents. Thus, the compositions of the present invention may have a
pH of between 3 and 12 and preferably a pH of less than 8.
[0063] This pH can be adjusted to the desired value by means of
acidifying or basifying agents usually used for dyeing.
[0064] The dye composition in accordance with the invention can
also contain various adjuvants conventionally used in compositions
for dyeing, and in particular for dyeing the hair, such as
surfactants, polymers, inorganic or organic thickeners,
anti-oxidants, penetrating agents, sequestering agents, fragrances,
buffers, dispersants or conditioning agents.
[0065] Needless to say, a person skilled in the art will take care
to select this or these optional additional compounds mentioned
above such that the advantageous properties intrinsically
associated with the dye composition in accordance with the
invention are not, or are not substantially, adversely affected by
the addition or additions envisaged.
[0066] The ready-to-use dye composition according to the invention
can be in various forms, such as in the form of liquids, creams or
gels or in any other form which is suitable for dyeing, and in
particular dyeing keratin substances.
[0067] Another subject of the invention relates to a dyeing process
in which at least one dye composition as defined above is applied
to a support for a period which is sufficient to develop the
desired coloration.
[0068] Preferably, the support used in this dyeing process consists
of keratin substances. In this case, the time required to develop
the coloration may be from about 1 minute to 1 hour and more
specifically from 5 to 40 minutes. After this application to the
keratin substances, they are rinsed, optionally washed with
shampoo, rinsed again and dried.
[0069] In another embodiment of the process of the invention, the
said process comprises a preliminary step which consists in
separately storing, on the one hand, a composition (A) comprising,
in a medium which is suitable for dyeing, at least one compound of
formula (I) as defined above, and, on the other hand, a composition
(B) containing, in a medium which is suitable for dyeing, at least
one oxidizing agent as defined above, and then in mixing them
together at the time of use, after which this mixture is applied to
the support.
[0070] The present invention also relates to a multi-compartment
dyeing device or "kit" comprising a first compartment containing
the composition (A) defined above and a second compartment
containing the composition (B) defined above.
[0071] When the oxidizing agent of composition (B) corresponds to
an enzyme, this enzyme can be in the form of powder or immobilized,
i.e. bound to a matrix.
[0072] These devices can be equipped with a means for applying the
desired mixture to the hair, such as the devices described in
patent FR 2,586,913.
[0073] The examples which follow are intended to illustrate the
invention without, however, limiting its scope.
[0074] The dye compositions below, in accordance with the
invention, were prepared:
1 Example 1 2 3 4 Resveratrol (compound 5.26 5.26 5.26 5.26 of
formula (I)) mmol mmol mmol mmol 5,6-Dihydroxyindoline -- 0.173 --
-- mmol 2,4-Diaminophenoxy- -- -- 0.173 -- ethanol dihydro- mmol
chloride 5,6-Dihydroxyindole -- -- -- 0.173 mmol Caffeic acid 0.173
-- -- -- mmol Laccase 0.002 g 0.002 g 0.002 g 0.002 g Phosphate
buffer 100 ml 100 ml 100 ml 100 ml pH 7.2 qs
[0075]
2 Example 5 6 7 8 9 Resveratrol 5.26 5.26 5.26 5.26 5.26 (compound
of mmol. mmol mmol mmol mmol formula (I)) 2,4-Diaminophen- -- -- --
0.173 -- oxyethanol mmol dihydrochloride 5,6-Dihydroxy- -- -- -- --
0.173 indole mmol Paraphenylene- 0.173 -- -- -- -- diamine mmol
Caffeic acid -- -- 0.173 -- -- mmol Laccase 0.002 g -- -- -- --
Tyrosinase -- 0.068 g 0.068 g 0.068 g 0.068 g Phosphate buffer 100
ml 100 ml 100 ml 100 ml 100 ml pH 7.2 qs
[0076] Each of the above dye compositions was applied to locks of
natural grey hair containing 90% white hairs for 30 minutes at
37.degree. C.
[0077] The locks were then rinsed, washed with shampoo, rinsed
again and then dried.
[0078] The hair was dyed in a shade given in the table below:
3 EXAMPLE SHADE OBTAINED 1 Very light golden blond 2 Light ash
blond 3 Slightly matt light ash blond 4 Matt slightly golden light
ash blond 5 Slightly golden matt blond 6 Light golden blond 7 Light
golden blond 8 Slightly matt very light ash blond 9 Ash blond
* * * * *