FIELD OF THE INVENTION
5 The present invention relates to a pretreatment composition of a process for dyeing or
bleaching keratin fibers, comprising at least 5% by weight of one or more particular amino
acids and at least 5% by weight of one or more monoalcohols, and also to a dyeing or
bleaching process using the pretreatment composition.
10 BACKGROUND OF THE INVENTION
It is known practice to perform hair dyeing or bleaching processes to modify the color of
natural hair. These processes generally consist in applying to the keratin fibers hair
compositions comprising chemical oxidizing agents and optionally direct dyes and/or
oxidation dyes.
15 These dyeing or bleaching hair compositions do, admittedly, have dyeing or bleaching
power, but they may occasionally be responsible for degradation of the quality of the fiber,
the constituent proteins of the hair possibly being denatured, thus giving rise to labile
proteins. The higher the content of labile proteins, the more the hair is damaged. This
degradation of the fiber quality may result in substantial breakage during combing of the
20 hair, notably when these compositions are applied to sensitized hair. Thus, it is common
practice to resort to care compositions involving conditioning agents in order to limit the
degradation or to improve the cosmetic properties of the hair. However, these care
compositions may, in certain cases, impair the dyeing or bleaching of the keratin fibers
thus treated.
25 There is thus a real need to develop a composition that can be used as a pretreatment
composition for a dyeing or bleaching process, which makes it possible to conserve or
even to improve the quality of the keratin fibers and notably to reduce the breakage that
may be observed during the dyeing or bleaching process, while at the same time avoiding
impairment of the dyeing or bleaching of the keratin fibers thus treated. Such a
30 composition must also be easy to use, notably easy to apply and stable, making it
possible to maintain or even to improve the cosmetic properties of the keratin fibers thus
treated, for example as regards the sheen, the soft feel, the suppleness, the appearance
or the disentangling. Furthermore, such a composition will ideally need to be compatible
with any type of dyeing or bleaching composition that is commercially available.
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The Applicant has discovered, surprisingly, that all of these objectives can be achieved
by means of the composition according to the present invention.
SUMMARY OF THE INVENTION
5 According to a first aspect, a subject of the present invention is a composition (A)
comprising:
10
i) at least 5% by weight, relative to the total weight of composition (A), of one or more
amino acids chosen from the compounds of formula (l1), salts thereof and mixtures
thereof:
COOH
I
H- C- N(H)
I p
R
(h)
in which formula (l1):
• p is an integer equal to 1 or 2;
• when p = 1, R forms with the nitrogen atom a saturated 5- to 8-membered, preferably
5-membered, heterocycle, this ring possibly being optionally substituted with at least one
15 group chosen from hydroxyl or (C1-C4)alkyl;
• when p = 2, R represents:
-a hydrogen atom; or
- a (C1-C12)alkyl group, preferably a (C1-C4)alkyl group, interrupted with at least one
heteroatom or group chosen from -S-, -N H- or -C(N H)- and/or substituted with at least
20 one group chosen from hydroxyl, amino or -NH-C(NH)-NH2; and
ii) at least 5% by weight, relative to the total weight of composition (A), of one or more
monoalcohols.
According to a second aspect, a subject of the present invention is a process for dyeing
25 or bleaching keratin fibers, comprising the following successive steps:
i) applying to the keratin fibers a composition (A) as defined previously;
ii) applying to the keratin fibres a dyeing or bleaching composition.
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According to a third aspect, a subject of the present invention is the use of a composition
(A) as defined previously, as a pretreatment composition of a dyeing or bleaching
process.
5 According to a fourth aspect, a subject of the present invention is the use of a
composition (A) as defined previously, for protecting keratin fibers, preferably for
protecting them against breakage, during a dyeing or bleaching treatment.
According to a fifth aspect, a subject of the present invention is a multi-compartment
10 device comprising:
• a first compartment containing a composition (A) as defined previously; and
• a second compartment containing a composition comprising at least one chemical
oxidizing agent; and
• optionally a third compartment containing a composition compns1ng at least one
15 coloring agent chosen from oxidation dyes, direct dyes and mixtures thereof.
DETAILED DESCRIPTION OF THE INVENTION
For the purposes of the present invention and unless otherwise indicated:
• the term "keratin fibers" means fibers of human or animal origin, such as head hair,
20 bodily hair, the eyelashes, the eyebrows, wool, angora, cashmere or fur. According to
the present invention, the keratin fibers are preferably human keratin fibers, more
preferentially the hair.
• the term "successive steps" means steps performed in the indicated order.
• the term "dye composition" means a composition comprising at least one coloring
25 agent.
• the term "bleaching composition" means a composition comprising at least one
chemical oxidizing agent.
• the term "alkyl group" means a linear or branched, saturated hydrocarbon-based
radical.
30 • the term "(Cx-Cy)alkyl group" means an alkyl group comprising from x toy carbon atoms.
• the term "coloring agent" means an oxidation dye, a direct dye or a pigment.
• the term "oxidation dye" means an oxidation dye precursor chosen from oxidation bases
and couplers. Oxidation bases and couplers are colorless or sparingly colored
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compounds, which, via a condensation reaction in the presence of an oxidizing agent,
give a colored species.
• the term "direct dye" means a natural and/or synthetic dye, including in the form of an
extract or extracts, other than oxidation dyes. These are colored compounds that will
5 spread superficially on the fiber. They may be ionic or nonionic, i.e. anionic, cationic,
neutral or nonionic.
• the term "reducing agent" means an agent that is capable of reducing the disulfide
bonds of the hair, such as compounds chosen from thiols, alkaline sulfites, hydrides and
phosphines.
10 • the term "chemical oxidizing agent" means an oxidizing agent other than atmospheric
oxygen.
Unless otherwise indicated, when compounds are mentioned in the present patent
application, this also includes the optical isomers thereof, the geometrical isomers
thereof, the tautomers thereof, the salts thereof or the solvates thereof, alone or as a
15 mixture.
The expressions "at least one" and "one or more" are synonymous and may be used
interchangeably.
Composition (A)
20 According to a first aspect, a subject of the present invention is a composition (A) as
defined previously. The Applicant has found, surprisingly, that composition (A) according
to the invention can be used as a pretreatment composition for a dyeing or bleaching
process, which makes it possible to conserve or even to improve the quality of the keratin
fibers and to reduce the breakage that may be observed during the dyeing or bleaching
25 process, while at the same time avoiding impairment of the dyeing or bleaching.
Furthermore, composition (A) according to the invention is compatible with any type of
dyeing or bleaching composition that is commercially available.
Amino acids
30 Composition (A) comprises one or more amino acids chosen from the compounds of
formula (l1) as defined previously, salts thereof and mixtures thereof, preferably chosen
from the compounds of formula (l1).
5
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The salts of compounds of formula (l1) comprise the salts with organic or mineral bases,
for example the salts of alkali metals, for instance the lithium, sodium or potassium salts;
the salts of alkaline-earth metals, for instance the magnesium or calcium salts, and the
zinc salts.
The compounds of formula (l1) may be in the form of an optical isomer of L, D or DL
configuration, preferably of L configuration.
As examples according to the present invention of compounds of formula (l1) in the form
10 of an optical isomer of L configuration, mention may be made of L-proline, L-methionine,
L-serine, L-arginine and L-lysine.
15
Preferably, the amino acid(s) included in composition (A) are chosen from glycine,
proline, methionine, serine, arginine, lysine, salts thereof and mixtures thereof.
More preferentially, the amino acid(s) included in composition (A) are chosen from
glycine, proline, methionine, serine, salts thereof and mixtures thereof.
Even more preferentially, the amino acid included in composition (A) is chosen from
20 glycine, salts thereof and mixtures thereof.
As examples of glycine salts that may be used in the present invention mention may be
made of sodium glycinate, zinc glycinate, calcium glycinate, magnesium glycinate,
manganese glycinate and potassium glycinate, preferably sodium glycinate or potassium
25 glycinate.
Particularly preferably, the amino acid included in composition (A) is glycine.
The amino acid(s) chosen from the compounds of formula (l1), salts thereof and mixtures
30 thereof are present in composition (A) in a total content of at least 5% by weight,
preferably of at least 8% by weight, relative to the total weight of composition (A).
The amino acid(s) chosen from the compounds of formula (l1), salts thereof and mixtures
thereof may be present in composition (A) in a total content ranging from 5% to 20% by
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weight, preferably ranging from 5% to 15% by weight, more preferentially ranging from
8% to 12% by weight, relative to the total weight of composition (A).
Composition (A) may preferably comprise at least 5% by weight, more preferentially at
5 least 8% by weight, of glycine, salts thereof and mixtures thereof relative to the total
weight of composition (A).
10
Preferably, composition (A) comprises from 5% to 20% by weight, preferably from 5% to
15% by weight and more preferentially from 8% to 12% by weight of glycine, salts thereof
and mixtures thereof relative to the total weight of composition (A).
According to a preferred embodiment, composition (A) comprises one or more amino
acids chosen from the compounds of formula (l1) as defined previously.
According to this preferred embodiment, the amino acid(s) included in composition (A)
are preferably chosen from glycine, proline, methionine, serine, arginine, lysine and
15 mixtures thereof, more preferentially from glycine, proline, methionine, serine and
mixtures thereof, and, even more preferentially, the amino acid included in composition
(A) is glycine.
According to this preferred embodiment, the amino acid(s) chosen from the compounds
20 of formula (l1) are present in composition (A) in a total content of at least 5% by weight,
preferably of at least 8% by weight, relative to the total weight of composition (A).
According to this preferred embodiment, the amino acid(s) chosen from the compounds
of formula (l1) are present in composition (A) in a total content preferably ranging from
25 5% to 20% by weight, more preferentially ranging from 5% to 15% by weight, even more
preferentially ranging from 8% to 12% by weight, relative to the total weight of
composition (A).
According to this preferred embodiment, composition (A) may preferably comprise at
30 least 5% by weight, more preferentially at least 8% by weight, of glycine relative to the
total weight of composition (A).
According to this preferred embodiment, composition (A) preferably comprises from 5%
to 20% by weight, more preferentially from 5% to 15% by weight and even more
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preferentially from 8% to 12% by weight of glycine relative to the total weight of
composition (A).
Qlj
5 Composition (A) may have a pH ranging from 2 to 11. Preferably, the pH of composition
(A) ranges from 4 to 10. More preferentially, the pH of composition (A) ranges from 8 to
10.
By way of example, the pH of composition (A) may be equal to 9.
The pH of composition (A) may be adjusted with at least one organic or mineral acid, or
10 with at least one alkaline agent chosen from mineral or organic or hybrid alkaline agents
and mixtures thereof.
The term "organic acid" means an acid, i.e. a compound that is capable of releasing a
cation or proton W or H30+, in aqueous medium, which includes at least one optionally
unsaturated, linear or branched C1-C2o hydrocarbon-based chain, a (hetero)cycloalkyl or
15 (hetero)aryl group and at least one acidic chemical function chosen in particular from
carboxyl C(O)OH, sulfonic S03H, sulfinic S02H, phosphonic P03H and phosphinic
P02H2.
More particularly, the organic or mineral acid used is chosen from hydrochloric acid HCI,
hydrobromic acid HBr, sulfuric acid H2S04, alkylsulfonic acids: (C1-C5)Aik-S(0)20H such
20 as methylsulfonic acid and ethylsulfonic acid; arylsulfonic acids: Ar-S(0)20H such as
benzenesulfonic acid and toluenesulfonic acid; (C1-C5)alkoxysulfinic acids: Alk-0-
S(O)OH such as methoxysulfinic acid and ethoxysulfinic acid; aryloxysulfinic acids such
as tolueneoxysulfinic acid and phenoxysulfinic acid; phosphoric acid H3P04; triflic acid
CF3S03H and tetrafluoroboric acid HBF4, and carboxylic acid(s) of formula (II) below and
25 the salts thereof:
I 0\\ l OH lHaTTA~o
in which formula (II):
(II)
A represents a saturated or unsaturated, cyclic or noncyclic, aromatic or nonaromatic
hydrocarbon-based group, which is monovalent when t is 0 or polyvalent when t is
30 greater than or equal to 1, comprising from 1 to 50 carbon atoms, which is optionally
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interrupted with one or more heteroatoms and/or optionally substituted, notably with one
or more hydroxyl groups; preferably, A represents a monovalent (C1-C5)alkyl group or a
polyvalent (C1-C5)alkylene group optionally substituted with one or more hydroxyl
groups.
5 In particular, the acid used is chosen from the carboxylic acids of formula (II) as defined
previously. Preferably, the acid used is an a-hydroxy acid such as lactic acid, glycolic
acid, tartaric acid or citric acid.
The mineral alkaline agents are preferably chosen from aqueous ammonia, alkaline
10 carbonates or bicarbonates such as sodium or potassium carbonates and sodium or
potassium bicarbonates, sodium hydroxide or potassium hydroxide, and mixtures
thereof.
The organic alkaline agents are preferably chosen from organic amines, i.e. they contain
at least one substituted or unsubstituted amino group.
15 The organic alkaline agents are more preferentially chosen from organic amines with a
pKb at 25°C of less than 12, preferably of less than 10 and even more advantageously
of less than 6. It should be noted that it is the pKb corresponding to the function which
has the highest basicity.
20 The organic alkaline agents are chosen, for example, from alkanolamines,
oxyethylenated and/or oxypropylenated ethylenediamines and the compounds of
formula (Ill) below:
in which formula (Ill):
25 • W is a divalent C1-C6 alkylene group optionally substituted with a hydroxyl group or a
(C1-C5)alkyl group, and/or optionally interrupted with one or more heteroatoms such as
oxygen or NRu;
• Rx, RY, Rz Rt and Ru, which may be identical or different, represent a hydrogen atom
or a group chosen from (C1-C5)alkyl, C1-C6 hydroxyalkyl or C1-C6 aminoalkyl.
30 Preferably, the alkanolamine is ethanolamine (or monoethanolamine).
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In one variant of the invention, composition (A) comprises, as alkaline agent, one or more
alkanolamines (preferably ethanolamine) and aqueous ammonia. In this variant, the
alkanolamine(s) are present in a predominant amount relative to the aqueous ammonia.
5 Hybrid alkaline agents that may be mentioned include the salts of the amines mentioned
previously with acids such as carbonic acid or hydrochloric acid.
Cationic polymers
Composition (A) may comprise one or more cationic polymers.
10 The term "cationic polymer'' means any polymer comprising cationic groups and/or
groups that can be ionized into cationic groups and not comprising any anionic groups
and/or groups that can be ionized into anionic groups. Preferably, the cationic polymer
is hydrophilic or amphiphilic.
The preferred cationic polymers are chosen from those that contain units including
15 primary, secondary, tertiary and/or quaternary amine groups that may either form part of
the main polymer chain or may be borne by a side substituent directly connected thereto.
The cationic polymers that may be used preferably have a weight-average molar mass
(Mw) ranging from 500 to 5x 106 g/mol and preferably ranging from 103 to 3x 106 g/mol.
Preferably, composition (A) comprises one or more cationic polymers chosen from
20 homopolymers or copolymers including in their structure one or more units
corresponding to formula (I) or (II):
in which:
(CH2 )k
/ ~
-(CH }t- - CR C(R12)-GH2-
2 I 12 I
H2C CH2
~ /
N
I
R,o
· k and tare equal to 0 or 1, the sum k + t being equal to 1;
25 • R12 denotes a hydrogen atom or a methyl group;
• R1o and R11, independently of each other, denote a (C1-C5)alkyl group, a C1-Cs
hydroxyalkyl group, a C1-C4 amidoalkyl group; or alternatively R1o and R11 denote,
together with the nitrogen atom to which they are attached, a heterocyclic group such as
5
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piperidyl or morpholinyl; preferably, R1o and R11, independently of each other, denote a
(C1-C4)alkyl group;
• y- is an anion preferably chosen from bromide, chloride, acetate, borate, citrate,
tartrate, bisulfate, bisulfite, sulfate and phosphate.
More preferentially, composition (A) comprises one or more cationic polymers chosen
from homopolymers or copolymers including in their structure one or more units
corresponding to formula (I) as defined previously.
Even more preferentially, composition (A) comprises one or more cationic polymers
10 chosen from homopolymers of diallyldimethylammonium salts and copolymers of
diallyldimethylammonium salts and of acrylamide.
Particularly preferably, composition (A) comprises one or more cationic polymers chosen
from copolymers of diallyldimethylammonium salts and of acrylamide.
15 Mention may be made more particularly of the homopolymer of dimethyldiallylammonium
salts (for example chloride) for example sold under the name Merquat 100 by the
company Nalco and the copolymers of diallyldimethylammonium salts (for example
chloride) and of acrylamide, notably sold under the name Merquat 550 or Merquat 7SPR.
The cationic polymer(s) may be present composition (A) in a total content ranging from
20 0.00001% to 5% by weight, preferably ranging from 0.00005% to 1% by weight and more
preferentially ranging from 0.00007% to 0.5% by weight, relative to the total weight of
composition (A).
Amino silicones
25 Composition (A) may comprise one or more silicones, preferably chosen from amino
silicones.
The term "amino silicone" means any silicone including at least one primary, secondary
or tertiary amine function.
The weight-average molecular masses of these amino silicones may be measured by
30 gel permeation chromatography (GPC) at room temperature (25°C), as polystyrene
equivalent. The columns used are 1-1 styragel columns. The eluent is THF and the flow
rate is 1 ml/min. 200 1-11 of a 0.5% by weight solution of silicone in THF are injected.
Detection is performed by refractometry and UV-metry.
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Preferably, the amino silicones are chosen from the amino silicones of formula (B) below:
R'aG3-a-Si(OSiG2)n-(OSiG~;R'2-b)m-O-SiG3-a-R'a (B)
in which:
- G, which may be identical or different, denotes a hydrogen atom or a group from among
5 phenyl, OH, C1-Cs alkyl, for example methyl, or C1-Cs alkoxy, for example methoxy,
- a, which may be identical or different, denotes 0 or an integer from 1 to 3, in particular
0,
- b denotes 0 or 1, in particular 1,
- m and n are numbers such that the sum (n + m) ranges from 1 to 2000 and in particular
10 from 50 to 150, n possibly denoting a number from 0 to 1999 and notably from 49 to 149,
and m possibly denoting a number from 1 to 2000 and notably from 1 to 10,
- R', which may be identical or different, denotes a monovalent radical of formula
-CqH2qL in which q is a number ranging from 2 to 8 and L is an optionally quaternized
amine group chosen from the following groups:
15 - N(R")2; -W(R"h A-; -NR"-Q-N(R")2 and -NR"-Q-W(R"h A-,
in which R", which may be identical or different, denotes hydrogen, phenyl, benzyl, or a
saturated monovalent hydrocarbon-based radical, for example a C1-C2o alkyl radical; Q
denotes a linear or branched group of formula CrH2r, r being an integer ranging from 2 to
6, preferably from 2 to 4; and A represents a cosmetically acceptable anion, notably a
20 halide such as fluoride, chloride, bromide or iodide.
More preferentially, the amino silicones are chosen from the amino silicones of formula
(F) below:
CHs c CH3
I I I
-Si 0 R2
I
(F)
CH3
p
I
N
25 in which:
5
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- p and q are numbers such that the sum (p + q) ranges from 1 to 1000, in particular from
50 to 350 and more particularly from 150 to 250; p possibly denoting a number from 0 to
999, notably from 49 to 349 and more particularly from 159 to 239, and q possibly
denoting a number from 1 to 1000, notably from 1 to 10 and more particularly from 1 to
5;
- R1 and R2, which are different, represent a hydroxyl or C1-C4 alkoxy radical, at least one
of the radicals R1 or R2 denoting an alkoxy radical.
Preferably, the alkoxy radical is a methoxy radical.
The hydroxy/alkoxy mole ratio generally ranges from 1 :0.8 to 1:1.1 and preferably from
10 1:0.9 to 1:1 and more particularly is equal to 1:0.95.
The weight-average molecular mass (Mw) of the silicone preferably ranges from 2000 to
200 000, even more particularly from 5000 to 100 000 and more particularly from 10 000
to 50 000.
The commercial products comprising silicones of structure (F) may include in their
15 composition one or more other amino silicones whose structure is different from that of
formula (F).
A product containing amino silicones of structure (F) is sold by Wacker under the name
Fluid WR 1300®.
Among the amino silicones of formula (F), mention may also be made of the product
20 Belsil ADM Log 1 from Wacker.
When these amino silicones are used, one particularly advantageous embodiment
consists in using them in the form of an oil-in-water emulsion. The oil-in-water emulsion
may comprise one or more surfactants. The surfactants may be of any nature but are
25 preferably cationic and/or nonionic. The number-average size of the silicone particles in
the emulsion generally ranges from 3 nm to 500 nanometers.
The silicone(s) may be present in composition (A) in a total content ranging from 0.001%
to 10% by weight, preferably ranging from 0.01% to 5% by weight, more preferentially
30 ranging from 0.02% to 1% by weight, even more preferentially ranging from 0.05% to
0.5% by weight relative to the total weight of composition (A).
The amino silicone(s) may be present composition (A) in a total content ranging from
0.001% to 10% by weight, preferably ranging from 0.01% to 5% by weight, more
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preferentially ranging from 0.02% to 1% by weight and even more preferentially ranging
from 0.05% to 0.5% by weight, relative to the total weight of composition (A).
Composition (A) preferably comprises a total content of coloring agents and/or reducing
5 agents of less than 0.1% by weight, more preferentially less than 0.01% by weight, even
more preferentially less than 0.001% by weight, relative to the total weight of composition
(A).
According to a particularly preferred embodiment, composition (A) is free of coloring
10 agents and/or reducing agents.
15
20
Composition (A) preferably comprises a total content of chemical oxidizing agents of less
than 0.1% by weight, more preferentially less than 0.01% by weight, even more
preferentially less than 0.001% by weight, relative to the total weight of composition (A).
Surfactants
Composition (A) preferably comprises less than 5% by weight, more preferentially less
than 2% by weight and even more preferentially less than than 1% by weight of
surfactants relative to the total weight of composition (A).
In particular, composition (A) may comprise a total content of anionic surfactants of less
than 0.1% by weight, preferably less than 0.01% by weight, more preferentially less than
0.001% by weight, relative to the total weight of composition (A).
25 According to a particularly preferred embodiment, composition (A) is free of anionic
surfactants.
30
Composition (A) may comprise a total content of nonionic surfactants of less than 0.5%
by weight relative to the total weight of composition (A).
Monoalcohols
Composition (A) may comprise at least 5% by weight and preferably at least 8% by
weight, relative to the total weight of composition (A), of one or more monoalcohols. The
monoalcohols may be linear or branched.
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The monoalcohol(s) are preferably chosen from C2 to C6 monoalcohols, more
preferentially from C2 to C4 monoalcohols, even more preferentially from ethanol,
isopropanol, tert-butanol, n-butanol and mixtures thereof.
5 According to a particularly preferred embodiment, the monoalcohol is ethanol.
10
The monoalcohol(s) may be present in composition (A) in a total content ranging from
5% to 20% by weight, preferably ranging from 5% to 15% by weight, more preferentially
ranging from 8% to 12% by weight, relative to the total weight of composition (A).
Organic solvents
Composition (A) may comprise, in addition to the monoalcohol(s), at least one organic
solvent chosen from polyols, polyol ethers and mixtures thereof.
15 The polyols are preferably chosen from propylene glycol, dipropylene glycol, glycerol
and mixtures thereof.
20
25
The polyol ethers are preferably chosen from propylene glycol monomethyl ether,
diethylene glycol monomethyl ether and monoethyl ether and mixtures thereof.
Composition (A) may comprise a total content of organic solvents other than
monoalcohols ranging from 1% to 40% by weight, preferably ranging from 5% to 30% by
weight, more preferentially ranging from 8% to 15% by weight, relative to the total weight
of composition (A).
Water
Composition (A) may comprise a total content of water ranging from 1% to 90% by
weight, preferably ranging from 20% to 90%, more preferentially ranging from 40% to
90% by weight and even more preferentially ranging from 60% to 85% by weight, relative
30 to the total weight of composition (A).
Dyeing or bleaching process
5
10
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According to a second aspect, a subject of the present invention is a process for dyeing
or bleaching keratin fibers, comprising the following successive steps:
i) applying to the keratin fibres a composition (A) as defined previously;
ii) applying to the keratin fibres a dyeing or bleaching composition.
In the process according to the present invention, it is essential for steps i) and ii) to be
successive, i.e. for step ii) to be performed after step i).
The process may comprise one or more additional steps between steps i) and ii), but,
even in such an embodiment, step ii) is always performed after step i).
Dyeing or bleaching composition
Chemical oxidizing agent
The dyeing or bleaching composition applied to the keratin fibers during step ii) of the
15 process may comprise at least one chemical oxidizing agent.
Preferably, the chemical oxidizing agent is chosen from hydrogen peroxide, urea
peroxide, alkali metal bromates, peroxygenated salts, peracids and precursors thereof,
and mixtures thereof.
20 More preferentially, the chemical oxidizing agent is chosen from hydrogen peroxide,
peroxygenated salts, and mixtures thereof.
Even more preferentially, the chemical oxidizing agent is chosen from hydrogen
peroxide, persulfates, perborates or percarbonates of alkali metals or alkaline-earth
metals or of ammonium, and mixtures thereof.
25 A chemical oxidizing agent that is particularly preferred is hydrogen peroxide.
Examples of peroxygenated salts that may be mentioned include sodium, potassium or
ammonium persulfates and mixtures thereof.
When the composition is a bleaching composition, it may preferably comprise hydrogen
30 peroxide and a peroxygenated salt.
The dyeing or bleaching composition may comprise a total content of chemical oxidizing
agents ranging from 0.5% to 60% by weight, preferably ranging from 0.5% to 40% by
weight, more preferentially ranging from 1% to 30% by weight, relative to the total weight
of the dyeing or bleaching composition.
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Liquid fatty substances
The dyeing or bleaching composition may also comprise one or more fatty substances
that are liquid at room temperature (25°C) and at atmospheric pressure (1.a13x 1 as Pa),
5 other than salified fatty acids.
The term "fatty substance" means an organic compound that is insoluble in water at room
temperature (25°C) and at atmospheric pressure (1.a13x1as Pa) (solubility of less than
5% by weight, preferably less than 1% by weight and even more preferentially less than
a.1% by weight). They bear in their structure at least one hydrocarbon-based chain
1 a including at least 6 carbon atoms and/or a sequence of at least two siloxane groups. In
addition, the fatty substances are generally soluble in organic solvents under the same
temperature and pressure conditions, for instance chloroform, dichloromethane, carbon
tetrachloride, ethanol, benzene, toluene, tetrahydrofuran (THF), liquid petroleum jelly or
decamethylcyclopentasiloxane.
15 The term "oil" means a "fatty substance" that is liquid at room temperature (25°C) and at
atmospheric pressure (1.a13x 1 as Pa).
The term "nonsilicone fatty substance" refers to a fatty substance not containing any
Si-0 bonds and the term "silicone fatty substance" refers to a fatty substance containing
at least one Si-0 bond.
2a The liquid fatty substances that may be used in the dyeing or bleaching composition are
different from salified fatty acids, i.e. they can be present in the composition in the form
of free fatty acids. In other words, these fatty substances do not contain any salified
carboxylic acid groups (-C(O)O-). In particular, these fatty substances are neither
polyoxyethylenated nor polyglycerolated.
25 Preferably, the fatty substances are different from non-salified fatty acids.
More particularly, the liquid fatty substances according to the invention are chosen from
C6 to C16 liquid hydrocarbons, liquid hydrocarbons comprising more than 16 carbon
atoms, nonsilicone oils of animal origin, oils of triglyceride type of plant or synthetic origin,
fluoro oils, liquid fatty alcohols, liquid fatty acid and/or fatty alcohol esters other than
3a triglycerides, and silicone oils, and mixtures thereof.
It is recalled that the fatty alcohols and esters more particularly contain at least one
saturated or unsaturated, linear or branched hydrocarbon-based group, comprising 6 to
3a and better still from 8 to 3a carbon atoms, which is optionally substituted, in particular,
with one or more hydroxyl groups (in particular 1 to 4). If they are unsaturated, these
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compounds may comprise one to three conjugated or unconjugated carbon-carbon
double bonds.
As regards the C6 to C16 liquid hydrocarbons, they are linear, branched or optionally
cyclic, and are preferably alkanes. Examples that may be mentioned include hexane,
5 cyclohexane, undecane, dodecane, isododecane, tridecane or isoparaffins, such as
isohexadecane or isodecane, and mixtures thereof.
The liquid hydrocarbons comprising more than 16 carbon atoms may be linear or
branched, and of mineral or synthetic origin, and are preferably chosen from liquid
paraffins or liquid petroleum jelly, polydecenes, hydrogenated polyisobutene such as
10 Parleam®, and mixtures thereof.
A hydrocarbon-based oil of animal origin that may be mentioned is perhydrosqualene.
The triglyceride oils of plant or synthetic origin are preferably chosen from liquid fatty
acid triglycerides including from 6 to 30 carbon atoms, for instance heptanoic or octanoic
acid triglycerides, or alternatively, for example, sunflower oil, corn oil, soybean oil,
15 marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara
oil, sunflower oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance
those sold by the company Stearinerie Dubois or those sold under the names Miglyol®
810, 812 and 818 by the company Dynamit Nobel, jojoba oil and shea butter oil, and
mixtures thereof.
20 As regards the fluoro oils, they may be chosen from perfluoromethylcyclopentane and
perfluoro-1 ,3-dimethylcyclohexane, sold under the names Flutec® PC1 and Flutec®
PC3 by the company BNFL Fluorochemicals; perfluoro-1 ,2-dimethylcyclobutane;
perfluoroalkanes such as dodecafluoropentane and tetradecafluorohexane, sold under
the names PF 5050® and PF 5060® by the company 3M, or bromoperfluorooctyl sold
25 under the name
Foralkyl® by the company Atochem; nonafluoromethoxybutane and
nonafluoroethoxyisobutane; perfluoromorpholine derivatives such as
4-trifluoromethylperfluoromorpholine sold under the name PF 5052® by the company
3M.
30 The liquid fatty alcohols may more particularly be chosen from linear or branched,
saturated or unsaturated alcohols, preferably unsaturated or branched alcohols,
including from 6 to 30 carbon atoms and preferably from 8 to 30 carbon atoms. Examples
that may be mentioned include octyldodecanol, 2-butyloctanol, 2-hexyldecanol,
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2-undecylpentadecanol, isostearyl alcohol, oleyl alcohol, linolenyl alcohol, ricinoleyl
alcohol, undecylenyl alcohol and linoleyl alcohol, and mixtures thereof.
As regards the liquid esters of fatty acids and/or of fatty alcohols other than the
triglycerides mentioned above, mention may be made notably of esters of saturated or
5 unsaturated, linear c1 to c26 or branched c3 to c26 aliphatic monoacids or polyacids and
of saturated or unsaturated, linear c1 to c26 or branched c3 to c26 aliphatic monoalcohols
or polyalcohols, the total carbon number of the esters being greater than or equal to 6
and more advantageously greater than or equal to 10.
Preferably, for the esters of monoalcohols, at least one from among the alcohol and the
10 acid from which the esters of the invention are derived is branched.
Among the monoesters, mention may be made of dihydroabietyl behenate; octyldodecyl
behenate; isocetyl behenate; isostearyl lactate; lauryl lactate; linoleyl lactate; oleyl
lactate; isostearyl octanoate; isocetyl octanoate; cetyl octanoate; decyl oleate; isocetyl
isostearate; isocetyl laurate; isocetyl stearate; isodecyl octanoate; isodecyl oleate;
15 isononyl isononanoate; isostearyl palmitate; methyl acetyl ricinoleate; cetyl
isononanoate; 2-ethylhexyl isononanoate; octyldodecyl erucate; oleyl erucate; ethyl
palmitate, isopropyl palmitate, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl
myristates such as isopropyl 2-octyldodecyl myristate, isobutyl stearate; 2-hexyldecyl
laurate, and mixtures thereof.
20
Preferably, among the monoesters of monoacids and of monoalcohols, use will be made
of ethyl palmitate, isopropyl palmitate, alkyl myristates such as isopropyl myristate or
ethyl myristate, isocetyl stearate, 2-ethylhexyl isononanoate, isodecyl neopentanoate
and isostearyl neopentanoate, and mixtures thereof.
25 Still within the context of this variant, use may also be made of esters of C4 to C22
dicarboxylic or tricarboxylic acids and of C1 to C22 alcohols and esters of mono-, di- or
tricarboxylic acids and of c2 to c26 di-, tri-, tetra- or pentahydroxy alcohols.
Mention may notably be made of: diethyl sebacate; diisopropyl sebacate; diisopropyl
adipate; di-n-propyl adipate; dioctyl adipate; diisostearyl adipate; dioctyl maleate;
30 glyceryl undecylenate; octyldodecyl stearoyl stearate; pentaerythrityl monoricinoleate;
pentaerythrityl tetraisononanoate; pentaerythrityl tetrapelargonate; pentaerythrityl
tetraisostearate; pentaerythrityl tetraoctanoate; propylene glycol dicaprylate; propylene
glycol dicaprate; tridecyl erucate; triisopropyl citrate; triisostearyl citrate; glyceryl
trilactate; glyceryl trioctanoate; trioctyldodecyl citrate; trioleyl citrate; propylene glycol
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dioctanoate; neopentyl glycol diheptanoate; diethylene glycol diisononanoate; and
polyethylene glycol distearates, and mixtures thereof.
The dyeing or bleaching composition may also comprise, as fatty ester, sugar esters and
diesters of C6 to C3o and preferably C12 to C22 fatty acids. It is recalled that the term
5 "sugar" refers to oxygen-bearing hydrocarbon-based compounds bearing several alcohol
functions, with or without aldehyde or ketone functions, and which include at least 4
carbon atoms. These sugars may be monosaccharides, oligosaccharides or
polysaccharides.
Examples of suitable sugars that may be mentioned include sucrose, glucose, galactose,
10 ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose, and
derivatives thereof, notably alkyl derivatives, such as methyl derivatives, for instance
methylglucose.
The sugar esters of fatty acids may be chosen notably from the group comprising the
esters or mixtures of esters of sugars described previously and of linear or branched,
15 saturated or unsaturated C6 to C3o and preferably C12 to C22 fatty acids. If they are
unsaturated, these compounds may comprise one to three conjugated or unconjugated
carbon-carbon double bonds.
The esters according to this variant may also be chosen from mono-, di-, tri- and
tetraesters, polyesters, and mixtures thereof.
20 These esters may be, for example, oleates, laurates, palmitates, myristates, behenates,
cocoates, stearates, linoleates, linolenates, caprates, arachidonates or mixtures thereof
notably such as the mixed oleo-palmitate, oleo-stearate and palmito-stearate esters
More particularly, use is made of monoesters and diesters and notably sucrose, glucose
or methylglucose mono- or di- oleates, stearates, behenates, oleopalmitates, linoleates,
25 linolenates and oleostearates, and mixtures thereof.
An example that may be mentioned is the product sold under the name Glucate® DO by
the company Amerchol, which is a methylglucose dioleate.
Preferably, use will be made of a liquid ester of a monoacid and of a monoalcohol.
The silicone oils that may be used in the dyeing or bleaching composition may be volatile
30 or nonvolatile, cyclic, linear or branched silicone oils, which are unmodified or modified
with organic groups, and preferably have a viscosity from 5x 1 o-6 to 2.5 m2/s at 25°C, and
preferably 1 X 1 o-s tO 1 m2/S.
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Preferably, the silicone oils are chosen from polydialkylsiloxanes, notably
polydimethylsiloxanes (PDMS), and liquid polyorganosiloxanes including at least one
aryl group.
These silicone oils may also be organomodified. The organomodified silicone oil(s) that
5 may be used in the dyeing or bleaching composition are preferably liquid silicones as
defined previously and including in their structure one or more organofunctional groups
attached via a hydrocarbon-based group, chosen, for example, from amine groups and
alkoxy groups.
Organopolysiloxanes are defined in greater detail in Walter Noll's Chemistry and
10 Technology of Silicones (1968), Academic Press. They may be volatile or nonvolatile.
When they are volatile, the silicone oils are more particularly chosen from those with a
boiling point of between 60°C and 260°C, and even more particularly from:
(i) cyclic polydialkylsiloxanes including from 3 to 7 and preferably from 4 to 5 silicon
atoms. These are, for example, octamethylcyclotetrasiloxane notably sold under the
15 name Volatile Silicone® 7207 by Union Carbide or Silbione® 70045 V2 by Rhodia,
decamethylcyclopentasiloxane sold under the name Volatile Silicone® 7158 by Union
Carbide, and Silbione® 70045 V5 by Rhodia, and mixtures thereof.
Mention may also be made of cyclocopolymers of the
dimethylsiloxane/methylalkylsiloxane type, such as Volatile Silicone® FZ 3109 sold by
20 the company Union Carbide.
Mention may also be made of mixtures of cyclic polydialkylsiloxanes with organosilicon
compounds, such as the mixture of octamethylcyclotetrasiloxane and
tetra(trimethylsilyl)pentaerythritol (50/50) and the mixture of
octamethylcyclotetrasiloxane and oxy-1, 1 '-bis(2,2,2' ,2' ,3,3' -hexatrimethylsilyloxy)-
25 neopentane;
(ii) linear volatile polydialkylsiloxanes containing 2 to 9 silicon atoms and having a
viscosity of less than or equal to 5x 1 o-6 m2/s at 25°C. An example is
decamethyltetrasiloxane notably sold under the name SH 200 by the company Toray
Silicone. Silicones falling within this category are also described in the article published
30 in Cosmetics and Toiletries, Vol. 91, Jan. 76, pages 27-32 - Todd & Byers Volatile
Silicone Fluids for Cosmetics.
Nonvolatile polydialkylsiloxanes are preferably used.
These silicone oils are more particularly chosen from polydialkylsiloxanes, among which
mention may be made mainly of polydimethylsiloxanes bearing trimethylsilyl end groups.
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The viscosity of the silicones is measured at 25°C according to ASTM standard 445
Appendix C.
Among these polydialkylsiloxanes, mention may be made, in a nonlimiting manner, of
the following commercial products:
5 -the Silbione® oils of the 47 and 70 047 series or the Mirasil® oils sold by Rhodia, for
instance the oil 70 047 V 500 000;
- the oils of the Mirasil® series sold by the company Rhodia;
- the oils of the 200 series from the company Dow Corning, such as DC200 with a
viscosity of 60 000 mm2/s;
10 - the Viscasil® oils from General Electric and certain oils of the SF series (SF 96, SF 18)
from General Electric.
Mention may also be made of polydimethylsiloxanes bearing dimethylsilanol end groups,
known under the name dimethiconol (CTFA), such as the oils of the 48 series from the
company Rhodia.
15 The organomodified silicones that may be used in the dyeing or bleaching composition
are silicones as defined previously and including in their structure one or more
organofunctional groups attached via a hydrocarbon-based group.
As regards the liquid polyorganosiloxanes including at least one aryl group, they may
notably be polydiphenylsiloxanes, and polyalkylarylsiloxanes functionalized with the
20 organofunctional groups mentioned previously.
The polyalkylarylsiloxanes are particularly chosen from linear and/or branched
polydimethyl/methylphenylsiloxanes and polydimethyl/diphenylsiloxanes with a viscosity
ranging from 1 X 1 o-s to 5x 1 o-2 m2/s at 25°C.
Among these polyalkylarylsiloxanes, examples that may be mentioned include the
25 products sold under the following names:
- the Silbione® oils of the 70 641 series from Rhodia;
- the oils of the Rhodorsil® 70 633 and 763 series from Rhodia;
- the oil Dow Corning 556 Cosmetic Grade Fluid from Dow Corning;
- the silicones of the PK series from Bayer, such as the product PK20;
30 -the silicones of the PN and PH series from Bayer, such as the products PN1000 and
PH1000;
- certain oils of the SF series from General Electric, such as SF 1023, SF 1154, SF 1250
and SF 1265.
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Among the organomodified silicones, mention may be made of polyorganosiloxanes
including:
- substituted or unsubstituted amine groups, such as the products sold under the names
GP 4 Silicone Fluid and GP 7100 by the company Genesee or the products sold under
5 the names Q2 8220 and Dow Corning 929 or 939 by the company Dow Corning. The
substituted amine groups are, in particular, c1 to c4 aminoalkyl groups;
- alkoxy groups;
- hydroxyl groups.
The liquid fatty substance(s) are preferentially chosen from liquid hydrocarbons
10 containing more than 16 carbon atoms, plant oils, liquid fatty alcohols and liquid fatty
esters, silicone oils and mixtures thereof.
Preferentially, the liquid fatty substance(s) are chosen from liquid hydrocarbons
comprising more than 16 carbon atoms, in particular liquid petroleum jelly.
15 In a particular embodiment, the total content of liquid fatty substance(s) included in the
dyeing or bleaching composition is greater than or equal to 20% by weight, preferably
greater than or equal to 30% by weight, more preferentially greater than or equal to 35%
by weight, relative to the total weight of the dyeing or bleaching composition.
More preferentially, the total content of liquid fatty substance(s) included in the dyeing or
20 bleaching composition ranges from 20% to 80% by weight, and preferably from 30% to
70% by weight, relative to the total weight of the dyeing or bleaching composition.
Alkaline agents
The dyeing or bleaching composition may optionally also comprise one or more alkaline
25 agents.
Preferably, the dyeing or bleaching composition comprises one or more organic or
mineral alkaline agents.
The mineral alkaline agent(s) are preferably chosen from aqueous ammonia, alkali metal
carbonates or bicarbonates such as sodium or potassium carbonates and sodium or
30 potassium bicarbonates, sodium or potassium hydroxide, alkali metal silicates or
metasilicates such as sodium or potassium silicates or metasilicates, or mixtures thereof.
The organic alkaline agent(s) are preferably chosen from organic amines with a pKb at
25°C of less than 12, preferably less than 10 and even more advantageously less than
6. It should be noted that it is the pKb corresponding to the function which has the highest
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basicity. In addition, the organic amines do not comprise any alkyl or alkenyl fatty chains
comprising more than ten carbon atoms.
The organic alkaline agent(s) are chosen, for example, from alkanolamines,
oxyethylenated and/or oxypropylenated ethylenediamines, amino acids and the
5 compounds of formula (Ill) below:
in which formula (Ill):
• W is a divalent C1-C6 alkylene group optionally substituted with a hydroxyl group or a
(C1-C5)alkyl group, and/or optionally interrupted with one or more heteroatoms such as
10 oxygen or NRu;
• Rx, RY, Rz Rt and Ru, which may be identical or different, represent a hydrogen atom
or a group chosen from (C1-C5)alkyl, C1-C6 hydroxyalkyl or C1-C6 aminoalkyl.
Examples of amines of formula (Ill) that may be mentioned include 1 ,3-diaminopropane,
15 1 ,3-diamino-2-propanol, spermine and spermidine.
The term "alkanolamine" means an organic amine comprising a primary, secondary or
tertiary amine function, and one or more linear or branched C1 to Cs alkyl groups bearing
one or more hydroxyl radicals.
Organic amines chosen from alkanolamines such as monoalkanolamines,
20 dialkanolamines or trialkanolamines comprising one to three identical or different C1 to
C4 hydroxyalkyl radicals are in particular suitable for performing the invention.
Among the compounds of this type, mention may be made of monoethanolamine (MEA),
diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine, N,Ndimethylethanolamine,
2-amino-2-methyl-1-propanol, triisopropanolamine, 2-amino-2-
25 methyl-1 ,3-propanediol, 3-amino-1 ,2-propanediol, 3-dimethylamino-1 ,2-propanediol and
tris(hydroxymethyl)aminomethane.
More particularly, the amino acids that may be used are of natural or synthetic origin, in
their L, D or racemic form, and include at least one acid function chosen more particularly
from carboxylic acid, sulfonic acid, phosphonic acid and phosphoric acid functions. The
30 amino acids may be in neutral or ionic form.
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As amino acids that may be used in the dyeing or bleaching composition, mention may
notably be made of aspartic acid, glutamic acid, alanine, arginine, ornithine, citrulline,
asparagine, carnitine, cysteine, glutamine, glycine, histidine, lysine, isoleucine, leucine,
methionine, N-phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine and
5 valine.
10
Advantageously, the amino acids are basic amino acids comprising an additional amine
function optionally included in a ring or in a ureide function.
Such basic amino acids are preferably chosen from those corresponding to formula (IV)
below, and also salts thereof:
R.-CH2-CH(NH2)-C(O)-OH (fV)
in which R represents a group chosen from imidazolyl, preferably imidazolyl-4-yl;
aminopropyl; aminoethyl; -(CH2)2N(H)-C(O)-NH2; and -(CH2)2-N(H)-C(NH)-NH2.
The compounds corresponding to formula (IV) are histidine, lysine, arginine, ornithine
and citrulline.
15 The organic amine may also be chosen from organic amines of heterocyclic type.
Besides histidine that has already been mentioned in the amino acids, mention may in
particular be made of pyridine, piperidine, imidazole, triazole, tetrazole and
benzimidazole.
The organic amine may also be chosen from amino acid dipeptides. As amino acid
20 dipeptides that may be used in the present invention, mention may notably be made of
carnosine, anserine and balenine.
The organic amine may also be chosen from compounds including a guanidine function.
As amines of this type that may be used in the present invention, besides arginine, which
has already been mentioned as an amino acid, mention may be made notably of
25 creatine, creatinine, 1, 1-dimethylguanidine, 1, 1-diethylguanidine, glycocyamine,
metformin, agmatine, n-amidinoalanine, 3-guanidinopropionic acid, 4-guanidinobutyric
acid and 2-([amino(imino)methyl]amino)ethane-1-sulfonic acid.
Hybrid compounds that may be mentioned include the salts of the amines mentioned
previously with acids such as carbonic acid or hydrochloric acid.
30 Guanidine carbonate or monoethanolamine hydrochloride may be used in particular.
Preferably, the alkaline agent(s) present in the dyeing or bleaching composition are
chosen from aqueous ammonia, alkanolamines, alkali metal silicates, alkali metal
metasilicates and mixtures thereof.
5
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More preferentially, the alkaline agent present in the dyeing composition is
monoethanolamine.
More preferentially, the alkaline agent present in the bleaching composition is chosen
from sodium silicate, sodium metasilicate and mixtures thereof.
The total content of alkaline agents included in the dyeing or bleaching composition may
range from 0.01% to 30% by weight, and preferably from 0.1% to 20% by weight, relative
to the total weight of the dyeing or bleaching composition.
10 Solvents
The dyeing or bleaching composition may optionally also comprise one or more organic
solvents.
Examples of organic solvents that may be mentioned include linear or branched C2 to C4
alkanols, such as ethanol and isopropanol; glycerol; polyols and polyol ethers, for
15 instance 2-butoxyethanol, propylene glycol, hexylene glycol, dipropylene glycol,
propylene glycol monomethyl ether, diethylene glycol monomethyl ether and monoethyl
ether, and also aromatic alcohols or ethers, such as benzyl alcohol or phenoxyethanol,
and mixtures thereof.
The organic solvent(s) may be present in the dyeing or bleaching composition in a
20 content ranging from 0.01% to 30% by weight, preferably ranging from 2% to 25% by
weight, relative to the total weight of the dyeing or bleaching composition.
Dye composition
According to a particular embodiment of the invention, the composition applied to the
25 keratin fibers during step ii) of the process is a dye composition.
The dye composition may comprise at least one coloring agent chosen from oxidation
dyes, direct dyes, and mixtures thereof, preferably from oxidation dyes.
30 Oxidation dyes
The oxidation dyes are generally chosen from one or more oxidation bases optionally
combined with one or more coupling agents (also known as couplers).
Oxidation bases
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The dye composition may optionally comprise one or more oxidation bases
advantageously chosen from those conventionally used in the dyeing of keratin fibers.
By way of example, the oxidation bases are chosen from para-phenylenediamines,
5 bis(phenyl)alkylenediamines, para-aminophenols ortho-aminophenols and heterocyclic
bases, and the corresponding addition salts.
Among the para-phenylenediamines that may be mentioned are, for example, paraphenylenediamine,
para-toluenediamine, 2-chloro-para-phenylenediamine, 2,3-
dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-
1 0 para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N, N-dimethyl-paraphenylenediamine,
N, N-diethyl-para-phenylenediamine, N, N-dipropyl-paraphenylenediamine,
4-amino-N, N-diethyl-3-methylaniline, N, N-bis(l3-hydroxyethyl)-paraphenylenediamine,
4-N, N-bis(l3-hydroxyethyl)amino-2-methylaniline, 4-N, N-bis(l3-
hydroxyethyl)amino-2-chloroaniline, 2-13-hydroxyethyl-para-phenylenediamine,
15 2-methoxymethyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine,
2-isopropyl-para-phenylenediamine, N-(13-hydroxypropyl)-para-phenylenediamine,
2-hydroxymethyl-para-phenylenediamine, N, N-dimethyl-3-methyl-paraphenylenediamine,
N-ethyi-N-(13-hydroxyethyl)-para-phenylenediamine, N-(13.vd
i hyd roxypropyl)-para-phenylenediam i ne, N-( 4' -ami nophenyl)-para-phenylenediam i ne,
20 N-phenyl-para-phenylenediamine, 2-13-hydroxyethyloxy-para-phenylenediamine,
2-13-acetylaminoethyloxy-para-phenylenediamine, N-(13-methoxyethyl)-paraphenylenediamine,
4-aminophenylpyrrolidine, 2-thienyl-para-phenylenediamine,
2-13-hydroxyethylamino-5-aminotoluene and 3-hydroxy-1-(4'-aminophenyl)pyrrolidine,
and the corresponding addition salts with an acid.
25 Among the para-phenylenediamines mentioned above, para-phenylenediamine, paratoluenediamine,
2-isopropyl-para-phenylenediamine, 2-13-hydroxyethyl-paraphenylenediamine,
2-13-hydroxyethyloxy-para-phenylenediamine, 2,6-dimethyl-paraphenylenediamine,
2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-paraphenylenediam
ine, N, N-bis(l3-hydroxyethyl)-para-phenylenediamine, 2-chloro-para-
30 phenylenediamine and 2-13-acetylaminoethyloxy-para-phenylenediamine, and the
corresponding addition salts with an acid, are particularly preferred.
Among the bis(phenyl)alkylenediamines that may be mentioned, for example, are N,N'bis(~-
hydroxyethyi)-N, N' -bis(4' -aminophenyl)-1 ,3-diaminopropanol, N, N' -bis(~hydroxyethyi)-
N, N' -bis(4' -aminophenyl)ethylenediamine, N, N' -bis(4-aminophenyl)-
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tetramethylenediamine, N, N' -bis(~-hydroxyethyi)-N, N' -bis(4-aminophenyl)tetramethylenediamine,
N, N' -bis(4-methylaminophenyl)-tetramethylenediamine, N, N'bis(
ethyi)-N, N' -bis(4' -amino-3' -methylphenyl)ethylenediamine and 1 ,8-bis(2,5-
diaminophenoxy)-3,6-dioxaoctane, and the corresponding addition salts.
5 Among the para-aminophenols that are mentioned are, for example, para-aminophenol,
4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-chlorophenol, 4-amino-3-
hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol,
4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(13-
hydroxyethylaminomethyl)phenol and 4-amino-2-fluorophenol, and the corresponding
10 addition salts with an acid.
Among the ortho-aminophenols that may be mentioned, for example, are
2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and 5-acetamido-2-
aminophenol, and the corresponding addition salts.
Among the heterocyclic bases that may be mentioned, for example, are pyridine,
15 pyrimidine and pyrazole derivatives.
Among the pyridine derivatives that may be mentioned are the compounds described,
for example, in patents GB 1 026 978 and GB 1 153 196, for example
2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine and 3,4-
diaminopyridine, and the corresponding addition salts.
20 Other pyridine oxidation bases that are useful in the present invention are the
3-aminopyrazolo[1 ,5-a]pyridine oxidation bases or the corresponding addition salts
described, for example, in patent application FR 2 801 308. Examples that may be
mentioned include pyrazolo[1 ,5-a]pyrid-3-ylamine, 2-acetylaminopyrazolo[1 ,5-a]pyrid-3-
ylamine, 2-(morpholin-4-yl)pyrazolo[1 ,5-a]pyrid-3-ylamine, 3-aminopyrazolo[1 ,5-
25 a]pyridine-2-carboxylic acid, 2-methoxypyrazolo[1 ,5-a]pyrid-3-ylamine, (3-
aminopyrazolo[1 ,5-a]pyrid-7 -yl)methanol, 2-(3-aminopyrazolo[1 ,5-a]pyrid-5-yl)ethanol,
2 -(3-am i nopyrazol o[ 1 , 5-a] pyrid-7 -yl)ethanol, (3-am i nopyrazol o[ 1 , 5-a] pyrid-2-
yl)methanol, 3,6-diaminopyrazolo[1 ,5-a]pyridine, 3,4-diaminopyrazolo[1 ,5-a]pyridine,
pyrazolo[1 ,5-a]pyridine-3, 7 -diamine, 7 -(morpholin-4-yl)pyrazolo[1 ,5-a]pyrid-3-ylamine,
30 pyrazolo[1 ,5-a]pyridine-3,5-diamine, 5-(morpholin-4-yl)pyrazolo[1 ,5-a]pyrid-3-ylamine,
2-[(3-aminopyrazolo[1 ,5-a]pyrid-5-yl)(2-hydroxyethyl)amino]ethanol,
2-[(3-aminopyrazolo[1 ,5-a]pyrid-7 -yl)(2-hydroxyethyl)amino]ethanol,
3-am i nopyrazol o[ 1 , 5-a ]pyrid i n-5-ol, 3-am i nopyrazol o[ 1 , 5-a ]pyrid i n-4-ol,
3-am i nopyrazol o[ 1 , 5-a ]pyrid i n-6-ol, 3-am i nopyrazol o[ 1 , 5-a ]pyrid i n-7 -ol,
wo 2022/003039 PCT/EP2021/068033
28
2-13-hydroxyethoxy-3-aminopyrazolo[1 ,5-a]pyridine and 2-(4-dimethylpiperazinium-1-yl)-
3-aminopyrazolo[1 ,5-a]pyridine, and the corresponding addition salts.
More particularly, the oxidation bases that are useful in the present invention are chosen
from 3-aminopyrazolo[1 ,5-a]pyridines and are preferably substituted on carbon atom 2
5 with:
a) a (di)(C1-C5)(alkyl)amino group, said alkyl group possibly being substituted with at
least one hydroxyl, amino or imidazolium group;
b) an optionally cationic 5- to ?-membered heterocycloalkyl group comprising from 1 to
3 heteroatoms, optionally substituted with one or more (C1-C5)alkyl groups such as a
10 di(C1-C4)alkylpiperazinium group; or
c) a (C1-C5)alkoxy group optionally substituted with one or more hydroxyl groups, such
as a 13-hydroxyalkoxy group, and the corresponding addition salts.
Among the pyrimidine derivatives that may be mentioned are the compounds described,
for example, in patents DE 2359399; JP 88-169571; JP 05-63124; EP 0770375 or patent
15 application WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-
triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-
diaminopyrimidine, 2,5,6-triaminopyrimidine and the addition salts thereof and the
tautomeric forms thereof, when a tautomeric equilibrium exists.
Among the pyrazole derivatives that may be mentioned are the compounds described in
20 patents DE 3843892 and DE 4133957 and patent applications WO 94/08969, WO
94/08970, FR-A-2 733 749 and DE 195 43 988, for instance 4,5-diamino-1-
methylpyrazole, 4,5-diamino-1-(13-hydroxyethyl)pyrazole, 3,4-diaminopyrazole, 4,5-
diamino-1-(4'-chlorobenzyl)pyrazole, 4,5-diamino-1 ,3-dimethylpyrazole, 4,5-diamino-3-
methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1 ,3-
25 dimethyl-5-hydrazinopyrazole, 1-benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-
tert-butyl-1-methylpyrazole, 4,5-diamino-1-tert-butyl-3-methylpyrazole, 4,5-diamino-1-
(13-hydroxyethyl)-3-methylpyrazole, 4, 5-diamino-1-ethyl-3-methylpyrazole, 4, 5-diamino-
1-ethyl-3-( 4' -methoxyphenyl)pyrazole, 4, 5-diamino-1-ethyl-3-hydroxymethylpyrazole,
4, 5-diamino-3-hydroxymethyl-1-methylpyrazole, 4,5-diamino-3-hydroxymethyl-1-
30 isopropylpyrazole, 4,5-diamino-3-methyl-1-isopropylpyrazole, 4-amino-5-(2'-
aminoethyl)amino-1 ,3-dimethylpyrazole, 3,4,5-triaminopyrazole, 1-methyl-3,4,5-
triaminopyrazole, 3,5-diamino-1-methyl-4-methylaminopyrazole and 3,5-diamino-4-(13-
hydroxyethyl)amino-1-methylpyrazole, and the corresponding addition salts. Use may
also be made of 4,5-diamino-1-(13-methoxyethyl)pyrazole.
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29
A 4,5-diaminopyrazole will preferably be used and even more preferentially 4,5-diamino-
1-(13-hydroxyethyl)pyrazole and/or a corresponding salt.
The pyrazole derivatives that may also be mentioned comprise diamino-N,Ndihydropyrazolopyrazolones
and in particular those described in patent application FRS
A-2 886 136, such as the following compounds and the corresponding addition salts:
2,3-diamino-6, 7 -dihydro-1 H ,5H-pyrazolo[1 ,2-a]pyrazol-1-one, 2-amino-3-ethylamino-
6, 7 -dihydro-1 H ,5H-pyrazolo[1 ,2-a]pyrazol-1-one, 2-amino-3-isopropylamino-6, 7-
dihydro-1 H ,5H-pyrazolo[1 ,2-a]pyrazol-1-one, 2-amino-3-(pyrrolidin-1-yl)-6, 7 -dihydro-
1 H ,5H-pyrazolo[1 ,2-a]pyrazol-1-one, 4,5-diamino-1 ,2-dimethyl-1 ,2-dihydropyrazol-3-
10 one, 4,5-diamino-1 ,2-diethyl-1 ,2-dihydropyrazol-3-one, 4,5-diamino-1 ,2-bis(2-
hyd roxyethyl)-1 , 2 -d i hyd ropyrazol-3-one, 2 -ami no-3-(2 -hyd roxyethyl) ami no-6, 7 -d i hydro-
1 H ,5H-pyrazolo[1 ,2-a]pyrazol-1-one, 2-amino-3-dimethylamino-6, 7 -dihydro-1 H ,5Hpyrazolo[
1 ,2-a]pyrazol-1-one, 2,3-diamino-5,6,7,8-tetrahydro-1 H,6H-pyridazino[1 ,2-
a] pyrazol-1-one, 4-am i no-1 , 2 -d iethyl-5-(pyrrol id i n-1-yl)-1 , 2 -d i hyd ropyrazol-3-one,
15 4-amino-5-(3-dimethylaminopyrrolidin-1-yl)-1 ,2-diethyl-1 ,2-dihydropyrazol-3-one and
2,3-diamino-6-hydroxy-6, 7 -dihydro-1 H ,5H-pyrazolo[1 ,2-a]pyrazol-1-one.
Use will preferably be made of 2,3-diamino-6,7-dihydro-1 H,5H-pyrazolo[1 ,2-a]pyrazol-1-
one and/or a corresponding salt.
Heterocyclic bases that will preferably be used are 4,5-diamino-1-(13-
20 hydroxyethyl)pyrazole and/or 2,3-diamino-6, 7 -dihydro-1 H ,5H-pyrazolo[1 ,2-a]pyrazol-1-
one and/or a corresponding salt.
Coupling agents
The dye composition may optionally comprise one or more coupling agents
25 advantageously chosen from those conventionally used in the dyeing of keratin fibers.
Among these coupling agents, mention may be made in particular of metaphenylenediamines,
meta-aminophenols, meta-diphenols, naphthalene-based coupling
agents and heterocyclic coupling agents, and also the corresponding addition salts.
Mention may be made, for example, of 1 ,3-dihydroxybenzene, 1 ,3-dihydroxy-2-
30 methylbenzene, 4-chloro-1 ,3-dihydroxybenzene, 2,4-diamino-1-(13-
hydroxyethyloxy)benzene, 2-amino-4-(13-hydroxyethylamino )-1-methoxybenzene, 1 ,3-
diaminobenzene, 1 ,3-bis(2,4-diaminophenoxy)propane, 3-ureidoaniline, 3-ureido-1-
dimethylaminobenzene, sesamol, 1-13-hydroxyethylamino-3,4-methylenedioxybenzene,
a-naphthol, 2-methyl-1-naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-Nwo
2022/003039 PCT/EP2021/068033
30
methylindole, 2-amino-3-hydroxypyridine, 6-hydroxybenzomorpholine, 3,5-diamino-2,6-
dimethoxypyridine, 1-N-(13-hydroxyethyl)amino-3,4-methylenedioxybenzene, 2,6-bis(l3-
hydroxyethylamino)toluene, 6-hydroxyindoline, 2,6-dihydroxy-4-methylpyridine, 1-H-3-
methylpyrazol-5-one, 1-phenyl-3-methylpyrazol-5-one, 2,6-dimethylpyrazolo[1 ,5-b]-
5 1 ,2,4-triazole, 2,6-dimethyl[3,2-c]-1 ,2,4-triazole and 6-methylpyrazolo[1 ,5-
a]benzimidazole, 2-methyl-5-aminophenol, 5-N-(13-hydroxyethyl)amino-2-methylphenol,
3-aminophenol and 3-amino-2-chloro-6-methylphenol, the corresponding addition salts
with an acid and the corresponding mixtures.

CLAIMS
1. A composition (A) comprising:
i) at least 5% by weight, relative to the total weight of composition (A), of one or more
5 amino acids chosen from the compounds of formula (l1), salts thereof and mixtures
thereof:
COOH
I
H- C- N(H)
I p
R
(11)
in which formula (l1):
· p is an integer equal to 1 or 2;
10 • when p = 1, R forms with the nitrogen atom a saturated 5- to 8-membered, preferably
5-membered, heterocycle, this ring possibly being optionally substituted with at least one
group chosen from hydroxyl or (C1-C4)alkyl;
• when p = 2, R represents:
- a hydrogen atom; or
15 - a (C1-C12)alkyl group, preferably a (C1-C4)alkyl group, interrupted with at least one
heteroatom or group chosen from -S-, -N H- or -C(N H)- and/or substituted with at least
one group chosen from hydroxyl, amino or -NH-C(NH)-NH2; and
20
ii) at least 5% by weight, relative to the total weight of composition (A), of one or more
monoalcohols.
2. The composition (A) as claimed in claim 1, in which the amino acid(s) are chosen from
glycine, proline, methionine, serine, arginine, lysine, salts thereof and mixtures thereof,
preferably from glycine, proline, methionine, serine, salts thereof and mixtures thereof,
more preferentially from glycine, salts thereof and mixtures thereof; even more
25 preferentially, the amino acid is glycine.
3. The composition (A) as claimed in claim 1 or 2, in which the amino acid(s) are present
in composition (A) in a total content ranging from 5% to 20% by weight, preferably
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54
ranging from 5% to 15% by weight and more preferentially ranging from 8% to 12% by
weight, relative to the total weight of composition (A).
4. The composition (A) as claimed in any one of the preceding claims, in which the
5 monoalcohol(s) are chosen from c2 to c6 monoalcohols, preferably from c2 to c4
monoalcohols, more preferentially from ethanol, isopropanol, tert-butyl, n-butanol and
mixtures thereof; even more preferentially, the monoalcohol is ethanol.
5. The composition (A) as claimed in any one of the preceding claims, in which the
10 monoalcohol(s) are present in composition (A) in a total content ranging from 5% to 20%
by weight, preferably ranging from 5% to 15% by weight and more preferentially ranging
from 8% to 12% by weight, relative to the total weight of composition (A).
6. The composition (A) as claimed in any one of the preceding claims, in which the pH
15 of composition (A) is from 2 to 11, preferably from 4 to 10 and more preferentially from
8 to 10.
7. The composition (A) as claimed in any one of the preceding claims, in which
composition (A) comprises one or more cationic polymers, preferably chosen from
20 homopolymers or copolymers including in their structure one or more units
corresponding to formula (I) or (II):
in which:
(CH2 )k
/ ~
-(CH )t-- CR C(R12}-CH2-
2 I 12 I
H2C CH2
~ /
N
I
R,o
25 • k and t are equal to 0 or 1, the sum k + t being equal to 1;
• R12 denotes a hydrogen atom or a methyl group;
• R1o and R11, independently of each other, denote a (C1-C5)alkyl group, a C1-Cs
hydroxyalkyl group, a C1-C4 amidoalkyl group; or alternatively R1o and R11 denote,
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55
together with the nitrogen atom to which they are attached, a heterocyclic group such as
piperidyl or morpholinyl; preferably, R1o and R11, independently of each other, denote a
(C1-C4)alkyl group;
• y- is an anion preferably chosen from bromide, chloride, acetate, borate, citrate,
5 tartrate, bisulfate, bisulfite, sulfate and phosphate; more preferentially, the cationic
polymer(s) being chosen from homopolymers or copolymers including in their structure
one or more units corresponding to formula (I) as defined previously; even more
preferentially, the cationic polymer(s) being chosen from homopolymers of
diallyldimethylammonium salts and copolymers of diallyldimethylammonium salts and of
10 acrylamide; most preferentially, the cationic polymer(s) being chosen from copolymers
of diallyldimethylammonium salts and of acrylamide.
8. The composition (A) as claimed in the preceding claim, in which the cationic
polymer(s) are present in composition (A) in a total content ranging from 0.00001% to
15 5% by weight, preferably ranging from 0.00005% to 1% by weight and more preferentially
ranging from 0.00007% to 0.5% by weight, relative to the total weight of composition (A).
9. The composition (A) as claimed in any one of the preceding claims, in which
composition (A) comprises one or silicones, preferably chosen from amino silicones,
20 more preferentially chosen from the amino silicones of formula (F) below:
CH3 c CH3
I I I
-Si 0 R2
I
(F)
CH3
p
I
N
in which:
• p and q are numbers such that the sum (p+q) ranges from 1 to 1000, in particular from
50 to 350 and more particularly from 150 to 250; p possibly denoting a number from 0 to
25 999, notably from 49 to 349 and more particularly from 159 to 239, and q possibly
5
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56
denoting a number from 1 to 1000, notably from 1 to 10 and more particularly from 1 to
s· ,
• R1 and R2, which are different, represent a hydroxyl or C1-C4 alkoxy radical, at least
one of the radicals R1 or R2 denoting an alkoxy radical.
10. The composition (A) as claimed in the preceding claim, in which the silicone(s) are
present in composition (A) in a total content ranging from 0.001% to 10% by weight,
preferably ranging from 0.01% to 5% by weight, more preferentially from 0.02% to 1%
by weight and better still from 0.05% to 0.5% by weight relative to the total weight of
10 composition (A).
11. The composition (A) as claimed in any one of the preceding claims, in which
composition (A) comprises a total content of coloring agents and/or reducing agents of
less than 0.1% by weight, preferably less than 0.01% by weight, more preferentially less
15 than 0.001% by weight relative to the total weight of composition (A); even more
preferentially, composition (A) is free of coloring agents and/or reducing agents.
12. The composition (A) as claimed in any one of the preceding claims, in which
composition (A) comprises a total content of anionic surfactants of less than 0.1% by
20 weight, preferably less than 0.01% by weight, more preferentially less than 0.001% by
weight relative to the total weight of composition (A); even more preferentially,
composition (A) is free of anionic surfactants.
13. A process for dyeing or bleaching keratin fibers, comprising the following successive
25 steps:
i) applying to the keratin fibers a composition (A) as defined in any one of claims 1 to 12;
ii) applying to the keratin fibers a dyeing or bleaching composition.
14. The process as claimed in the preceding claim, in which the dyeing or bleaching
30 composition comprises at least one chemical oxidizing agent, preferably chosen from
hydrogen peroxide, urea peroxide, alkali metal bromates, peroxygenated salts, peracids
and precursors thereof, and mixtures thereof, more preferentially from hydrogen
peroxide, peroxygenated salts and mixtures thereof, even more preferentially from
hydrogen peroxide, persulfates, perborates or percarbonates of alkali metals or alkalinewo
2022/003039 PCT/EP2021/068033
57
earth metals or of ammonium and mixtures thereof, most preferentially hydrogen
peroxide.
15. The process as claimed in claim 13 or 14, in which the composition applied during
5 step ii) is a dye composition comprising at least one coloring agent chosen from oxidation
dyes, direct dyes and mixtures thereof, preferably from oxidation dyes.
16. The process as claimed in any one of claims 13 to 15, also comprising, between
steps i) and ii), a step i') consisting in leaving composition (A) to stand on the keratin
10 fibers for a time ranging from 1 min to 60 min, preferably ranging from 3 min to 40 min
and more preferentially ranging from 3 min to 20 min.
17. The process as claimed in any one of claims 13 to 16, also comprising, after step i)
or i') and before step ii), a step of rinsing and/or drying the keratin fibers, preferably a
15 step of drying the keratin fibers.
18. The process as claimed in any one of claims 13 to 17, in which the process does not
comprise a rinsing step between step i) or i') and step ii).
20 19. The use of a composition (A) as defined in any one of claims 1 to 12, as a
pretreatment composition for a dyeing or bleaching process.
20. The use of a composition (A) as defined in any one of claims 1 to 12, for protecting
keratin fibers, preferably for protecting them from breakage, during a dyeing or bleaching
25 treatment.
21. A multi-compartment device comprising:
• a first compartment containing a composition (A) as defined in any one of claims 1 to
12; and
30 • a second compartment containing a composition comprising at least one chemical
oxidizing agent; and
• optionally a third compartment containing a composition compns1ng at least one
coloring agent chosen from oxidation dyes, direct dyes and mixtures thereof.