Cosmetic composition based on ellagic acid or a derivative thereof
and on a particular mixture of surfactants
The present invention relates to a cosmetic composition
5 compnsmg, in particular proportions, at least one compound selected
from ellagic acid, ethers thereof, the salts of these compounds, and
mixtures thereof, and a system of particular surfactants.
The present invention also relates to a cosmetic treatment
method using said composition and to the use of said composition for
10 washing keratin fibres, in particular human keratin fibres such as the
hair.
Ellagic acid is known in the pnor art for its use as an active
agent for preventing hair turning grey, or an antioxidant, depigmenting
or else anti-pollution active agent. It can also be used as an anti-
IS dandruff agent.
The problems of dandruff affect up to 50% of the world's
population. They affect both men and women and are perceived as
having a very negative psychosocial impact. The appearance of
dandruff is bothersome both from an aesthetic point of view and
20 because of the annoyances that it causes (itching, redness, etc.), with
the result that many people confronted with this problem to varying
degrees wish to be free of it in an effective and permanent manner.
Dandruff corresponds to excessive and visible desquamation of
the scalp resulting from excessively rapid multiplication of the
25 epidermal cells and their abnormal maturation. This phenomenon can
be caused in particular by microtraumas of physical or chemical
nature, such as hair treatments which are too aggressive, extreme
climatic conditions, nervousness, diet, fatigue or pollution, but it has
been demonstrated that dandruff conditions most commonly result
30 from a disorder of the microflora of the scalp, and more particularly
from excessive colonization by a fungus which belongs to the family
of yeasts of the Malassezia genus (formerly known as Pytirosporum)
and which is naturally present on the scalp.
It has been observed that since ellagic acid and derivatives
5
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thereof have very low solubility in water and in the solvents and oils
commonly used in cosmetic compositions, these compounds have the
drawback that they can be formulated virtually solely m dispersed
form.
It is therefore difficult to homogeneously incorporate ellagic
acid and derivatives thereof into cosmetic compositions, in particular
into washing compositions which comprise an aqueous medium,
without creating the formation of aggregates that can cause instability
of the composition over time and a loss of effectiveness.
10 Thus, there is a need to have a washing base which promotes
the dispersion of ellagic acid and of derivatives thereof by limiting the
formation of aggregates, and which allows a very good distribution of
these compounds during application and therefore optimum
effectiveness, while at the same time retaining good detergence, good
15 usage properties and good cosmetic properties.
Washing bases based on soaps of fatty acids or isolated
surfactants do not make it possible to obtain completely satisfactory
dispersions of ellagic acid or of derivatives thereof and/or result in
insufficient effectiveness and/or usage properties and/or cosmetic
20 properties.
The applicant has now found, surprisingly, that by combining,
in particular proportions, at least one compound selected from ellagic
acid, ethers thereof, ellagic acid salts and ellagic acid ether salts, with
a particular mixture of anionic surfactants or of amomc and
25 amphoteric or zwitterionic surfactants, it is possible to obtain a
washing composition for keratin fibres which is stable over time,
which exhibits a good dispersion of ellagic acid and/or of derivatives
thereof, and good usage and detergence properties, which confers good
distribution of the ellagic acid and derivatives thereof on the hair and
30 the scalp, and which is particularly effective, in particular as an antidandruff
composition.
In particular, it has been found that, when such a composition
is used, it distributes easily on the hair and the scalp, and generates an
abundant and soft foam that can be readily removed with water,
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resulting in soft, smooth, shiny clean hair. The composition according
to the invention also exhibits a particularly notable anti-dandruff
effectiveness, especially with repeated applications.
The composition according to the invention is stable over time
5 and does not result in the formation of aggregates. In particular, it has
a satisfactory storage stability both at ambient temperature (25°C) and
at higher temperature (37 or 45°C, for example).
A subject of the present invention is therefore a cosmetic
composition comprising, in a cosmetically acceptable medium:
10 (i) from 0.2% to 10% by weight of one or more compounds
selected from ellagic acid, ethers thereof, ellagic acid salts and ellagic
acid ether salts, and mixtures thereof, and
(ii) a system of surfactants selected from the following
mixtures comprising:
15 - (iii) one or more amomc surfactants selected from
ethoxylated alkyl sulphates, the corresponding acids, and mixtures
thereof, and (iv) one or more anionic surfactants different from the
abovementioned anionic surfactant(s) (iii), and
- (v) one or more anionic surfactants and (vi) one or more
20 amphoteric or zwitterionic surfactants, in a weight ratio of the amount
of anionic surfactant(s) to the amount of amphoteric or zwitterionic
surfactant(s) of greater than 3.
Another subject of the invention relates to a cosmetic treatment
method for keratin fibres, in particular for washing keratin fibres,
25 using said composition.
A subject of the invention IS also the use of said composition
for washing keratin fibres.
Other features, aspects, subjects and advantages of the present
invention will emerge more clearly on reading the description and the
30 examples which follow.
The composition according to the invention comprises one or
more compounds (i) selected from ellagic acid, ethers thereof, ellagic
acid salts, and ellagic acid ether salts.
Ellagic acid, also known as: 2,3, 7 ,8-tetrahydroxy( 1 )benzo5
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pyrano(5 ,4,3-cde )( 1 )benzopyran-5, 1 0-dione, is a well-known molecule
present in the plant kingdom. Reference may be made to the
publication ofthe Merck Index 20th edition (1996), No. 3588.
Ellagic acid has the following chemical formula:
HO
OH
HO
OH
0
which comprises four fused rings.
Ellagic acid is commercially available, especially from the
company Sigma, France.
10 Document FR-A-1 4 78 523 discloses a process for purifying
ellagic acid and also the purified ellagic acids obtained via such a
process.
The ellagic acid ether(s) that can be used according to the
invention is (are) preferably selected from the mono-, di-, tri- or
15 polyethers obtained by etherification of one or more hydroxyl groups
(one of the four OH groups of ellagic acid) of ellagic acid to give one
or more OR groups, R being selected from C2-C20 alkyl groups,
polyoxyalkylene groups, and in particular polyoxyethylene and/or
polyoxypropylene groups, and groups derived from one or more
20 monosaccharides or polysaccharides, such as, for example, the group
having the following formula:
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CH20H
H I c 0 H2C 0--CH 2
/~ \ I 0 H2C c \?H ~I c 1c /t \ c
OH C c H \9H H/] I I I H
H OH OH c c I H I OH
In the case of the di-, tri- or polyethers of ellagic acid, the R
groups as defined above may be identical or different.
Such ethers are described in Patent US 5,073,545. Preferably,
5 these ellagic acid ethers are selected from 3,4-di-0-methyl ellagic
acid, 3,3 ',4-tri-0-methyl ellagic acid and 3,3 '-di-0-methyl ellagic
acid.
The ellagic acid salt(s) and/or the ellagic acid ether salt(s) that
can be used according to the invention are preferably selected from the
10 salts of alkali or alkaline-earth metals, such as sodium, potassium,
calcium and magnesium, the ammonium salt and the amine salts, such
as the salts of triethanolamine, of monoethanolamine, of arginine and
of lysine. Preferably, the ellagic acid salt(s) and/or the ellagic acid
ether salt(s) that can be used according to the invention are selected
15 from the alkali or alkaline-earth metal salts, in particular the sodium,
potassium, calcium or magnesium salts.
Among all the compounds (i) mentioned, ellagic acid or a salt
thereof is preferably used.
The composition according to the invention preferably
20 comprises from 0.2% to 5% by weight, and even better still from 0.2%
to 2% by weight of compound(s) (i), relative to the total weight of the
composition.
25
The composition according to the invention comprises a system
of particular surfactants (ii) as mentioned above.
The term "anionic surfactant" means a surfactant comprising,
5
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as wmc or ionizable groups, only amomc groups. These amomc
groups are preferably selected from COzH, COz-. S03H, S03-, OS03H,
OS03 -. OzPOzH, OzPOzH- and OzPOz2
- groups.
According to a first embodiment, the composition according to
the invention comprises as system of surfactants, (iii) one or more
anionic surfactants selected from ethoxylated alkyl sulphates, the
corresponding acids, and mixtures thereof, and (iv) one or more
amomc surfactants different from the abovementioned amomc
10 surfactant(s) (iii). The ethoxylated alkyl sulphate(s) that can be used
in the composition according to the invention can be preferably
selected from ethoxylated (C6-C24)alkyl sulphates, in particular from
ethoxylated (C 8-C20)alkyl sulphates, and even better still ethoxylated
(C 12-C 14)alkyl sulphates, such as ethoxylated lauryl sulphate.
15 The alkyl group of these compounds may be linear or branched.
The alkyl group is preferably linear.
The number of ethylene oxide groups per molecule of
ethoxylated alkyl sulphate will preferably range from 1 to 50, better
still from 1 to 10, and even better still from 1 to 5. Even more
20 preferably, this number ranges from 2 to 3.
25
30
The constituent salt(s) of the ethoxylated alkyl sulphate can be
selected from alkali metal salts, such as the sodium salt, ammonium
salts, amine salts, and in particular aminoalcohol salts, and alkalineearth
metal salts, such as the magnesium salt.
By way of example of aminoalcohol salts, mention may m
particular be made of monoethanolamine, diethanolamine and
triethanolamine salts, monoisopropanolamine, diisopropanolamine or
triisopropanolamine salts, and 2-amino-2-methyl-1-propanol, 2-amino-
2-methyl-1 ,3-propanediol and tris(hydroxymethyl)aminomethane salts.
Alkali metal or alkaline-earth metal salts, and in particular
sodium or magnesium salts, are preferably used.
Among all the anionic surfactants (iii) mentioned, ethoxylated
sodium lauryl sulphate comprising from 2 to 3 mol of ethylene oxide is
preferably used.
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In this embodiment, the composition according to the invention
preferably comprises from 0.1% to 50% by weight, in particular from
2% to 20% by weight, even better still from 4% to 15%, and even
better still from 5% to 15% by weight of anionic surfactant(s) (iii),
5 relative to the total weight of the composition.
The anionic surfactant(s) (iv) different from the ethoxylated
alkyl sulphates and from their corresponding acids, that can be used
according to the invention, can be selected from the amomc
surfactants normally used in the cosmetics industry, other than the
10 ethoxylated alkyl sulphates and their corresponding acid forms (iii).
By way of example of anionic surfactants (iv) that can be used
in the composition according to the invention, mention may be made of
nonethoxylated alkyl sulphates, alkylamido ether sulphates, alkylaryl
polyether sulphates, monoglyceride sulphates, alkyl sulphonates,
15 alkylamide sulphonates, alkylarylsulphonates, alpha-olefin
sulphonates, paraffin sulphonates, alkylsulphosuccinates, alkyl ether
sulphosuccinates, alkylamide sulphosuccinates, alkyl sulphoacetates,
acylsarcosinates, acylglutamates, alkyl sulphosuccinamates, acyl
isethionates and N -acyltaurates; salts of alkyl mono esters of
20 polyglycoside-polycarboxylic acids, acyllactylates, salts of
D-galactosiduronic acids, salts of alkyl ether carboxylic acids, salts of
alkyl aryl ether carboxylic acids, salts of alkylamido ether carboxylic
acids; and the corresponding non-salified forms of all these
compounds; the alkyl and acyl groups of all these compounds
25 containing from 6 to 24 carbon atoms and the aryl group denoting a
phenyl group.
Some of these compounds may be oxyethylenated and then
preferably comprise from 1 to 50 ethylene oxide units, more
particularly from 1 to 10.
30 The salts of C6 _24 alkyl monoesters of polyglycosidepolycarboxylic
acids can be selected from C6 _24 alkyl polyglycosidecitrates,
c6-24 alkyl polyglycoside-tartrates and c6-24 alkyl
polyglycoside-sul phosuccinates.
When the anionic surfactant(s) (iv) IS (are) m salt form, it
5
10
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(they) can be selected from alkali metal salts, such as the sodium or
potassium salt, and preferably the sodium salt, ammonium salts
+
(NH4 ), amine salts, and in particular aminoalcohol salts, and alkalineearth
metal salts such as the magnesium salt.
By way of example of aminoalcohol salts, mention may in
particular be made of monoethanolamine, diethanolamine and
triethanolamine salts, monoisopropanolamine, diisopropanolamine or
triisopropanolamine salts, and 2-amino-2-methyl-1-propanol, 2-amino-
2-methyl-1 ,3-propanediol and tris(hydroxymethyl)aminomethane salts.
The alkali metal or alkaline-earth metal salts and in particular
the sodium or magnesium salts are preferably used.
Among all the anionic surfactants (iv) mentioned, the salts of
(C6_Cz4 alkyl) ether carboxylic acids and nonethoxylated (C6_Cz4)alkyl
sulphates are preferably used.
15 In particular, nonethoxylated (C6-C24)alkyl sulphates are
preferably used, and in particular sodium lauryl sulphate, magnesium
lauryl sulphate or ammonium lauryl sulphate. More preferably, sodium
lauryl sulphate is used.
In this embodiment, the composition according to the invention
20 preferably comprises from 0.1% to 30% by weight, in particular from
1% to 20% by weight, and better still from 2% to 15% by weight of
amomc surfactant(s) (iv), relative to the total weight of the
composition.
In one preferred embodiment, the amomc surfactant(s) (iii) is
25 (are) selected from ethoxylated (C6-C24 )alkyl sulphates comprising
from 1 to 50, preferably from 1 to 10, in particular from 1 to 5, and
even better still from 2 to 3 ethylene oxide units; and the anionic
surfactant(s) (iv) is (are) selected from (C 6-C24)alkyl sulphates.
In this preferred embodiment, the concentrations of amomc
30 surfactants (iii) and (iv) can be as described above.
Advantageously, in the composition according to the invention,
the weight ratio of the amount of anionic surfactant(s) (iii) to the amount
of anionic surfactant(s) (iv) ranges from 0.25 to 20, preferably from 0.5
to 10, better still from 1 to 5 and even better still from 1 to 2.5.
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In this embodiment, the composition according to the invention
can also comprise one or more additional surfactants selected from
amphoteric or zwitterionic surfactants.
By way of amphoteric or zwitterionic surfactants that can be
5 used, mention may be made of those described in the embodiment
below.
While they are present, the amount of the amphoteric or
zwitterionic surfactant(s) is preferably included in the range of from
0.01% to 20% by weight, even better still from 0.5% to 10% by
10 weight, relative to the total weight of the composition.
According to a second embodiment, the composition according
to the invention comprises, by way of system of surfactants, (v) one or
more anionic surfactants, and (vi) one or more amphoteric or
15 zwitterionic surfactants, in a weight ratio of the amount of anionic
surfactant(s) to the amount of amphoteric or zwitterionic surfactant(s)
of greater than 3.
By way of examples of anionic surfactants (v) that can be used in
the composition according to the invention mention may be made of alkyl
20 sulphates, alkyl ether sulphates, alkylamido ether sulphates, alkylaryl
polyether sulphates, monoglyceride sulphates, alkyl sulphonates,
alkylamide sulphonates, alkylarylsulphonates, alpha-olefin sulphonates,
paraffin sulphonates, alkylsulphosuccinates, alkyl ether sulphosuccinates,
alkylamide sulphosuccinates, alkyl sulphoacetates, acylsarcosinates,
25 acylglutamates, alkyl sulphosuccinamates, acyl isethionates and
N-acyltaurates; salts of alkyl monoesters of polyglycoside-polycarboxylic
acids, acyllactylates, salts of D-galactosiduronic acids, salts of alkyl ether
carboxylic acids, salts of alkyl aryl ether carboxylic acids, salts of
alkylamido ether carboxylic acids; and the corresponding non-salified
30 forms of all these compounds; the alkyl and acyl groups of all these
compounds containing from 6 to 24 carbon atoms and the aryl group
denoting a phenyl group.
Some of these compounds may be oxyethylenated and then
preferably comprise from 1 to 50 ethylene oxide units.
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The salts of C6 _24 alkyl monoesters of polyglycosidepolycarboxylic
acids can be selected from C6 _24 alkyl polyglycosidecitrates,
c6-24 alkyl polyglycoside-tartrates and c6-24 alkyl
polyglycoside-sul phosuccinates.
5 When the anionic surfactant(s) (v) is (are) in salt form, it
10
15
(they) can be selected from alkali metal salts, such as the sodium or
potassium salt, preferably the sodium salt, ammonium salts, amine
salts, and in particular aminoalcohol salts, or alkaline-earth metal salts
such as the magnesium salt.
By way of example of aminoalcohol salts, mention may in
particular be made of monoethanolamine, diethanolamine and
triethanolamine salts, monoisopropanolamine, diisopropanolamine or
triisopropanolamine salts, and 2-amino-2-methyl-1-propanol, 2-amino-
2-methyl-1 ,3-propanediol and tris(hydroxymethyl)aminomethane salts.
The alkali metal or alkaline-earth metal salts and in particular
the sodium or magnesium salts are preferably used.
Among all the anionic surfactants (v) mentioned, (C6 _C 24)alkyl
sulphates, (C6-C24)alkyl ether sulphates comprising from 2 to 50
ethylene oxide units, in particular in the form of alkali-metal,
20 ammonium, aminoalcohol and alkaline-earth metal salts, or a mixture
of these compounds, is preferably used.
In particular, (C 12-C20)alkyl sulphates, (C 12-C20)alkyl ether
sulphates comprising from 2 to 20 ethylene oxide units, in particular
in the form of alkali metal, ammonium, aminoalcohol and alkaline-
25 earth metal salts, or a mixture of these compounds, is preferably used.
Even better still, sodium lauryl ether sulphate comprising 2.2 mol of
ethylene oxide is preferably used.
In this embodiment, the composition according to the invention
preferably comprises from 0.1% to 50% by weight, in particular from
30 4% to 30% by weight, and even better still from 8% to 20% by weight
of anionic surfactant(s) (v), relative to the total weight of the
composition.
The amphoteric or zwitterionic surfactant(s) (vi) that can be
used in the present invention can in particular be derivatives of
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secondary or tertiary aliphatic ammes, which are optionally
quaternized, in which the aliphatic group is a linear or branched chain
containing from 8 to 22 carbon atoms, said amine derivatives
containing at least one anionic group such as, for example, a
5 carboxylate, sulfonate, sulphate, phosphate or phosphonate group.
Mention may in particular be made of (C 8 _ 20 )alkylbetaines,
sulphobetaines, (C 8 - 20 alkyl)amido(C2_8 alkyl)betaines or
(C 8 _20 alkyl)amido(C2_8 alkyl)sulphobetaines. Preferably, the betaine
amphoteric or zwitterionic surfactant(s) (vi) are selected from
10 (Cs-2o)alkylbetaines and (Cs-2o alkyl)amido(C2-s alkyl)betaines.
15
Among the optionally quaternized secondary or teriary
aliphatic amine derivatives that can be used, as defined above, mention
may also be made of the products of respective structures (A2) and
(A3) below:
in which:
Ra represents a C10-C30 alkyl or alkenyl group derived from an acid
Ra-COOH preferably present in hydrolysed coconut oil, a heptyl group,
20 a nonyl group or an undecyl group,
25
Rb represents a beta-hydroxyethyl group, and
Rc represents a carboxymethyl group;
and
Ra·-CONHCH2CH2-N(B)(B')
in which:
B represents -CH2CH20X',
B' represents -(CH2)z-Y', with z = 1 or 2,
(A3)
X' represents the -CH2-COOH, CH2-COOZ', -CH2CH2-COOH or
30 -CH2CH2-COOZ' group, or a hydrogen atom,
Y' represents -COOH, -COOZ', or the -CH2-CHOH-S03H or
-CH2-CHOH-S03Z' group,
Z' represents an ion derived from an alkali or alkaline-earth metal,
such as sodium, potassium or magnesium; an ammonium ion; or an ion
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derived from an organic amine and in particular from an aminoalcohol,
such as mono-, di- and triethanolamine, mono-, di- or
triisopropanolamine, 2-amino-2-methyl-1-propanol, 2-amino-2-methyl-
1 ,3-propanediol and tris(hydroxymethyl)aminomethane,
5 Ra· represents a C1o-C3o alkyl or alkenyl group of an acid Ra·COOH
preferably present in hydrolysed linseed oil or coconut oil, an alkyl
group, which is in particular C17 , and its iso form, or an unsaturated
cl7 group.
The compounds corresponding to formula (A3) are preferred.
10 These compounds are also classified in the CTF A dictionary,
5th edition, 1993, under the names disodium cocoamphodiacetate,
disodium lauroamphodiacetate, disodium caprylamphodiacetate,
disodium capryloamphodiacetate, disodium cocoamphodipropionate,
disodium lauroamphodipropionate, disodium caprylamphodipropionate,
15 disodium capryloamphodipropionate, lauroamphodipropionic acid and
cocoamphodipropionic acid.
By way of example, mention may be made of the
cocoamphodiacetate sold by the company Rhodia under the trade name
Miranol® C2M concentrate.
20 Among all the amphoteric or zwitterionic surfactants (vi)
mentioned above, (Cs-2o alkyl)betaines, (Cs-2o alkyl)amido(C2-s alkyl)betaines,
and mixtures thereof, are preferably used. More preferably,
the amphoteric or zwitterionic surfactant(s) is (are) selected from
cocoylamidopropylbetaine and cocoylbetaine.
25 In this embodiment, the composition according to the invention
preferably comprises from 0.01% to 20% by weight, in particular from
0.5% to 10% by weight, and even better still from 1% to 5% by weight
of amphoteric or zwitterionic surfactant(s) (vi), relative to the total
weight of the composition.
30 In one preferred embodiment, the amomc surfactant(s) (v) is
(are) selected from (C6-C24)alkyl sulphates and (C6-C24)alkyl ether
sulphates comprising from 2 to 50 ethylene oxide units; and the
amphoteric or zwitterionic surfactant(s) (vi) is (are) selected from
(Cs-2o alkyl)betaines, (Cs-2o alkyl)amido(C2-s alkyl)betaines and
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cocoamphodiacetates.
In one particularly preferred embodiment, the amomc
surfactant(s) (v) is (are) selected from (C 16)alkyl sulphates and
(C 16)alkyl ether sulphates in particular in the form of sodium salts
5 comprising from 2 to 10 ethylene oxide units; and the amphoteric or
zwitterionic surfactant(s) (vi) IS (are) selected from
cocoylamidopropylbetaine and cocoylbetaine.
In each of the preferred and particularly preferred embodiments
described above, the concentration of anionic surfactant(s) (v) and of
10 amphoteric or zwitterionic surfactant(s) (vi) can be as described
above.
Advantageously, the composition according to the invention
can comprise a weight ratio of the amount of anionic surfactant(s) (v)
to the amount of amphoteric or zwitterionic surfactant(s) (vi) of less
15 than or equal to 100, better still less than or equal to 50, and even
better still less than or equal to 20 and even more preferably less than
10.
The composition according to the invention may also comprise
one or more thickeners.
20 For the purpose of the present invention, the term "thickener"
means an agent which, introduced at 1% by weight into an aqueous
solution or aqueous-alcoholic solution containing 30% by weight of
ethanol, at pH = 7, makes it possible to achieve a viscosity of at least
100 cPs, preferably of at least 500 cPs, at 25°C and at a shear rate of
25 1 s- 1
. This viscosity may be measured using a cone/plate viscometer
(Haake R600 rheometer or the like).
The thickener(s) can be selected from sodium chloride, fatty
acid amides obtained from a C10-C30 carboxylic acid (coconut acid
monoisopropanolamide, diethanolamide or monoethanolamide,
30 oxyethylenated carboxylic acid monoethanolamide alkyl ether), nonionic
cellulosic thickeners (hydroxyethylcellulose, hydroxypropylcellulose,
carboxymethylcellulose), guar gum and non-wmc
derivatives thereof (hydroxypropylguar), gums of microbial origin
(xanthan gum, scleroglucan gum), crosslinked or non-crosslinked
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14
homopolymers and copolymers based on acrylic acid, on methacrylic
acid or on acrylamidopropanesulphonic acid, and the associative
polymers as described below, and mixtures thereof.
The associative polymer(s) that can be used according to the
5 invention are water-soluble polymers capable, in an aqueous medium,
of reversibly associating with one another or with other molecules.
Their chemical structure comprises hydrophilic zones and
hydrophobic zones characterized by at least one fatty chain preferably
comprising from 10 to 30 carbon atoms.
10 The associative polymer(s) that can be used according to the
invention may be of anionic, cationic, amphoteric or non-ionic type,
such as the polymers sold under the names Pemulen TR1 or TR2 by the
company Goodrich (INCI: Acrylates/C 10_30 Alkyl Acrylate
Crosspolymef), Salcare SC90 by the company Ciba, Aculyn 22, 28, 33,
15 44 or 46 by the company Rohm & Haas, and Elfacos T21 0 and T212 by
the company Akzo.
Among all the thickeners mentioned, the thickener(s) is (are)
preferably selected from acrylic acid-based or methacrylic acid-based
homopolymers and copolymers, which are preferably crosslinked,
20 and/or fatty acid amides obtained from a C10-C30 carboxylic acid.
Preferably, the cosmetic composition comprises from 0.1% to
20% by weight, and even better still from 0.2% to 10% by weight of
thickener(s), relative to the total weight of the composition.
The composition according to the invention may also comprise
25 one or more conditioning agents.
According to the present invention, the term "conditioning
agent" denotes any compound that can improve the cosmetic properties
of the hair, in particular the softness, disentangling, feel and static
electricity.
30 Preferably, the conditioning agent is selected from the group
comprising cationic polymers, cationic surfactants, silicones, such as
organosiloxanes, linear or branched C8-C 30 hydrocarbons, linear or
branched Cs-C3o fatty alcohols, esters of Cs-C3o fatty acid and of
C1-C3o alcohol, and in particular esters of Cs-C3o fatty acid and of
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15
Cs-C3o fatty alcohol, esters of C1-C7 acid or diacid and of Cs-C3o fatty
alcohol, ceramides or ceramide analogues, and mixtures of these
compounds.
The term "cationic polymer" means a polymer that is positively
5 charged when it is contained in the composition according to the
invention. This polymer may bear one or more positive permanent
charges or may contain one or more functions that are cationizable in
the composition according to the invention.
The cationic polymer(s) that may be used as conditioning
10 agents according to the present invention are preferably selected from
polymers comprising primary, secondary, tertiary and/or quaternary
amine groups forming part of the polymer chain or directly attached
thereto, and having a molecular weight of between 500 and about
5 000 000 and preferably between 1000 and 3 000 000.
15 When the conditioning agent is a cationic polymer, it is
preferably selected from those that contain units comprising 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 attached thereto.
20 Among the cationic polymers that may be mentioned more
25
particularly are polymers of the polyamine, polyamino amide and
polyquaternary ammonium type. These are known products. They are
described, for example, in French patents Nos. 2 505 348 and 2 542
997.
Among these polymers, mention may be made of:
( 1) homopolymers or copolymers derived from acrylic or
methacrylic esters or amides and comprising at least one of the units
of the following formulae:
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5 in which:
Rs
I -c-c-
H2 I
C=O
I
NH
I
A
I
/N""
R3 R4
16
(III)
PCT/EP2011/053013
Rs
I
-c-c-
H2 I
C=O
I
0
I X
A
I+
R-N-R
6 I 8
Ry
(II)
Rs
I -c-c-
H2 I
C=O
I
NH
I X
A
I+
R-N-R
6 I 8
Ry
(IV)
R3 and R4 , which may be identical or different, represent a
hydrogen atom or an alkyl group containing from 1 to 6 carbon atoms,
and preferably methyl or ethyl;
R5 , which may be identical or different, denote a hydrogen
10 atom or a CH3 group;
A, which may be identical or different, represent a linear or
branched alkyl group containing from 1 to 6 carbon atoms, preferably
2 or 3 carbon atoms, or a hydroxyalkyl group containing from 1 to 4
carbon atoms;
15 R6 , R7 and R8 , which may be identical or different, represent an
wo 2011/107467 PCT/EP2011/053013
17
alkyl group containing from 1 to 18 carbon atoms or a benzyl group,
and preferably an alkyl group containing from 1 to 6 carbon atoms;
x- denotes an anion derived from a mineral or organic acid,
such as a methosulphate anion or a halide such as chloride or bromide.
5 The copolymers of family (1) can also contain one or more
units derived from comonomers which may be selected from the family
of acrylamides, methacrylamides, diacetone acrylamides, acrylamides
and methacrylamides substituted on the nitrogen with lower (C 1-C4 )
alkyls, acrylic or methacrylic acids or esters thereof, vinyllactams
10 such as vinylpyrrolidone or vinylcaprolactam, and vinyl esters.
Thus, among these copolymers of family (1), mention may be
made of:
copolymers of acrylamide and of dimethylaminoethyl
methacrylate quaternized with dimethyl sulphate or with a dimethyl
15 halide, such as the product sold under the name Hercofloc by the
company Hercules,
- the copolymers of acrylamide and of methacryloyloxyethyltrimethylammonium
chloride described, for example, m Patent
Application EP-A-080 97 6 and sold under the name Bina Quat P 100
20 by the company Ciba Geigy,
-the copolymer of acrylamide and of
methacryloyloxyethyltrimethylammonium methosulphate sold under
the name Reten by the company Hercules,
- quaternized or non-quaternized vinylpyrrolidone/dialkyl-
25 aminoalkyl acrylate or methacrylate copolymers, such as the products
sold under the name Gafquat by the company ISP, such as, for
example, Gafquat 734 or Gafquat 755, or alternatively the products
known as Copolymer 845, 958 and 937. These polymers are described
in detail in French patents 2 077 143 and 2 393 573,
30 - dimethylamino ethy 1 methacrylate/vinylcaprolactam/vinylpyrrolidone
terpolymers, such as the product sold under the name
Gaffix VC 713 by the company ISP,
- vinylpyrrolidone/methacrylamidopropyldimethylamine
copolymers sold in particular under the name Styleze CC 10 by ISP,
wo 2011/107467 PCT/EP2011/053013
18
- quaternized vinylpyrrolidone/ dimethy laminopropylmethacrylamide
copolymers, such as the product sold under the name Gafquat
HS 100 by the company ISP, and
- crosslinked polymers of
5 methacryloyloxy(C 1-C4 )alkyl(C 1-C4 )trialkylammonium salts, such as
the polymers obtained by homopolymerization of dimethylaminoethyl
methacrylate quaternized with methyl chloride, or by copolymerization
of acrylamide with dimethylaminoethyl methacrylate quaternized with
methyl chloride, the homopolymerization or copolymerization being
10 followed by crosslinking with a compound comprising an olefinic
unsaturation, in particular methylenebisacrylamide. Use may more
particularly be made of an
acrylamide/methacryloyloxyethyltrimethylammonium chloride
crosslinked copolymer (20/80 by weight) in the form of a dispersion
15 containing 50% by weight of said copolymer in mineral oil. This
dispersion is sold under the name Salcare® SC 92 by the company
Ciba. A crosslinked methacryloyloxyethyltrimethylammonium chloride
homopolymer, for example as a dispersion in mineral oil or in a liquid
ester, can also be used. These dispersions are sold under the names
20 Salcare® SC 95 and Salcare® SC 96 by the company Ciba;
(2) polymers constituted of piperazinyl units and of
divalent alkylene or hydroxyalkylene groups containing straight or
branched chains, optionally interrupted with oxygen, sulphur or
nitrogen atoms or with aromatic or heterocyclic rings, and also the
25 oxidation and/or quaternization products of these polymers. Such
polymers are described, in particular, in French patents 2 162 025 and
2280361;
(3) water-soluble polyamino amides prepared in particular
by polycondensation of an acidic compound with a polyamine; these
30 polyamino amides can be crosslinked with an epihalohydrin, a
diepoxide, a dianhydride, an unsaturated dianhydride, a
his-unsaturated derivative, a bis-halohydrin, a bis-azetidinium, a bishaloacyldiamine,
a bis-alkyl halide or alternatively with an oligomer
resulting from the reaction of a bifunctional compound which is
wo 2011/107467 PCT/EP2011/053013
19
reactive with a bis-halohydrin, a bis-azetidinium, a bishaloacyldiamine,
a bis-alkyl halide, an epihalohydrin, a diepoxide or a
his-unsaturated derivative; the crosslinking agent being used in
proportions ranging from 0.025 to 0.35 mol per amine group of the
5 polyamino amide; these polyamino amides can be alkylated or, if they
contain one or more tertiary amine functions, they can be quaternized.
Such polymers are described, m particular, m French patents
2 252 840 and 2 368 508;
( 4) the polyamino amide derivatives resulting from the
10 condensation of polyalkylene polyamines with polycarboxylic acids,
followed by alkylation with bifunctional agents. Mention may be
made, for example, of adipic acid/dialkylaminohydroxyalkyldialkylenetriamine
polymers in which the alkyl groups contain from 1
to 4 carbon atoms and preferably denote a methyl, ethyl or propyl
15 group, and the alkylene groups contain from 1 to 4 carbon atoms and
preferably denote the ethylene group. Such polymers are in particular
described in French patent 1 583 363.
Among these derivatives, mention may be made more
particularly of the adipic acid/dimethylaminohydroxypropyldiethylene-
20 triamine polymers sold under the name Cartaretine F, F4 or F8 by the
company Sandoz.
(5) The polymers obtained by reaction of a polyalkylene
polyamine containing two primary amine groups and at least one
secondary amine group with a dicarboxylic acid selected from
25 diglycolic acid and saturated aliphatic dicarboxylic acids having from
3 to 8 carbon atoms. The molar ratio between the polyalkylene
polyamine and the dicarboxylic acid is between 0.8:1 and 1.4:1; the
polyamino amide resulting therefrom being reacted with
epichlorohydrin in a molar ratio of epichlorohydrin relative to the
30 secondary amine group of the polyamino amide of between 0.5:1 and
1. 8:1. Such polymers are described m particular m
US patents 3 227 615 and 2 961 347.
Polymers of this type are sold m particular under the name
Hercosett 57 by the company Hercules Inc. or alternatively under the
wo 2011/107467 PCT/EP2011/053013
20
name PD 170 or Delsette 101 by the company Hercules in the case of
the adipic acid/epoxypropyldiethylenetriamine copolymer.
(6) cyclopolymers of alkyldiallylamine or of
dialkyldiallylammonium, such as homopolymers or copolymers
5 containing, as main constituent of the chain, units corresponding to
formula (V) or (VI):
(V) (VI)
m which formulae 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; Rio
10 and RII, independently of each other, denote an alkyl group having
from 1 to 6 carbon atoms, a hydroxyalkyl group in which the alkyl
group preferably has 1 to 5 carbon atoms, a lower (CI-C4 ) amidoalkyl
group, or Rio and RII can denote, together with the nitrogen atom to
which they are attached, heterocyclic groups such as piperidinyl or
15 morpholinyl; y- is an anion such as bromide, chloride, acetate, borate,
citrate, tartrate, bisulphate, bisulphite, sulphate or phosphate. These
polymers are described in particular in French patent 2 080 759 and in
its Certificate of Addition 2 190 406.
Rio and RII, independently of each other, preferably denote an
20 alkyl group containing from 1 to 4 carbon atoms.
Among the polymers defined above, mention may be made
more particularly of the dimethyldiallylammonium chloride
homopolymer sold under the name Merquat 100 by the company Nalco
(and its homologues of low weight-average molecular mass) and the
25 copolymers of diallyldimethylammonium chloride and of acrylamide,
sold under the name Merquat 550.
wo 2011/107467 PCT/EP2011/053013
21
(7) the quaternary diammonium polymer containing
repeating units corresponding to formula (VII):
R13 R1s
I + I +
-N-A-N-B-
1 _1 I _1
X X
R14 R16 (VII)
in which formula (VII):
5 R13 , R14 , R15 et R16 , which may be identical or different,
represent aliphatic, alicyclic or arylaliphatic groups containing from 1
to 20 carbon atoms or lower (C 1-C4 ) hydroxyalkyl aliphatic groups, or
alternatively R13 , R14 , R15 and R16 , together or separately, constitute,
with the nitrogen atoms to which they are attached, heterocycles
10 optionally containing a second heteroatom other than nitrogen, or
alternatively R13, R14, R1s and R16 represent a linear or branched C1-C6
alkyl group substituted with a nitrile, ester, acyl or amide group or a
group -CO-O-R17-D or -CO-NH-R17-D or R17 is an alkylene having
from 1 to 10 carbon atoms and D a quaternary ammonium group;
15 A1 and B1 represent polymethylene groups containing from 2 to
20 carbon atoms which may be linear or branched, saturated or
unsaturated, and which may contain, linked to or intercalated in the
main chain, one or more aromatic rings or one or more oxygen, or
sulphur atoms or sulphoxide, sulphone, disulphide, amino, alkylamino,
20 hydroxyl, quaternary ammonium, ureido, amide or ester groups, and
x- denotes an anion derived from a mineral or organic acid;
A1, R13 and R15 can form, with the two nitrogen atoms to which
they are attached, a piperazine ring; in addition, if A1 denotes a linear
or branched, saturated or unsaturated alkylene or hydroxyalkylene
25 group, B1 can also denote a group
30
-(CHz)n-CO-D-OC-(CHz)pin
which:
n and p are integers ranging from 2 to 20 approximately,
D denotes:
a) a glycol residue of formula: -0-Z-0-, where Z denotes a
wo 2011/107467 PCT/EP2011/053013
22
linear or branched hydrocarbon-based group or a group corresponding
to one of the following formulae:
-(CHz-CHz-O)x -CHz-CHz-
- [ CHz -CH( CH3 )-0] y-CHz-CH( CH3 )-
5 where x and y denote an integer from 1 to 4, representing a
10
defined and unique degree of polymerization or any number from 1 to
4 representing an average degree of polymerization;
b) a bis-secondary diamine residue such
derivative;
0 0 as a p1perazme
c) a bis-primary diamine residue of formula: -NH-Y -NH-,
where Y denotes a linear or branched hydrocarbon-based group, or
alternatively the divalent group -CHz-CHz-S-S-CHz-CHz-;
d) a ureylene group of formula: -NH-CO-NH-.
Preferably, x- is an anion such as chloride or bromide.
15 These polymers generally have a number-average molecular
mass of between 1000 and 100 000.
Polymers of this type are described m particular in French
patents 2 320 330, 2 270 846, 2 316 271, 2 336 434 and 2 413 907 and
US patents 2 273 780, 2 375 853, 2 388 614, 2 454 547, 3 206 462,
20 2 261 002, 2 271 378, 3 874 870, 4 001 432, 3 929 990, 3 966 904,
4 005 193, 4 025 617, 4 025 627, 4 025 653, 4 026 945 and 4 027 020.
Use may more particularly be made of polymers which are
constituted of repeating units corresponding to formula (VIII):
1:8 ~~0
-NI (CH )-N-(CH) - 2 r I 2 s
R19 X R21 X
(VIII)
25 m which: R1s, R19, Rzo and Rz1, which may be identical or
30
different, denote an alkyl or hydroxyalkyl group containing from 1 to
4 carbon atoms approximately, r and s are integers ranging from 2 to
20 approximately, and x- is an anion derived from a mineral organic
acid.
A compound of formula (VIII) which is particularly preferred
wo 2011/107467 PCT/EP2011/053013
23
is the compound for which R1s, R19, Rzo and R21 representent a methyl
group and r = 3, s = 6 and X = Cl, referred to as hexadimethrine
chloride according to the INCI nomenclature (CTFA).
(8) Polyquaternary ammonium polymers constituted of units of
5 formula (IX):
~~ ~~ -N-(CH2)t-NH-CO-(CH2)u-CO-NH-(CH2)v-N-AI
x- I x-
R23 R2s
(IX)
in which formula:
Rn, R23, R24 and Rzs, which may be identical or different,
10 represent a hydrogen atom or a methyl, ethyl, propyl, ~-hydroxyethyl,
~-hydroxypropyl or -CHzCHz(OCHzCHz)pOH group, where p is equal
to 0 or to an integer ranging from 1 to 6, with the proviso that R22 ,
R23, R24 and Rzs do not simultaneously represent a hydrogen atom,
t and u, which may be identical or different, are integers
15 between 1 and 6,
v is equal to 0 or to an integer between 1 and 34,
x- denotes an anion such as a halide;
A denotes a group of a dihalide or preferably represents
-CHz-CHz-0-CHz-CHz-.
20 Compounds of this kind are described m particular in Patent
Application EP-A-122 324.
Among these products, mention may, for example, be made of
the products Mirapol® A 15, Mirapol® AD 1, Mira pol® AZ 1 and
Mirapol® 175 sold by the company Miranol.
25 (9) quaternary polymers of vinylpyrrolidone and of
vinylimidazole, such as, for example, the products sold under the
names Luviquat® FC 905, FC 550 and FC 370 by the company
B.A.S.F.
( 1 0) cationic polysaccharides, m particular cationic
30 celluloses and cationic cellulose derivatives and cationic
galactomannan gums.
wo 2011/107467 PCT/EP2011/053013
24
Among the cationic polysaccharides, mention may more
particularly be made of cellulose ether derivatives compnsmg
quaternary ammonmm
cellulose derivatives
groups,
grafted
cationic cellulose copolymers or
with a water-soluble quaternary
5 ammonium monomer and cationic galactomannan gums.
The cellulose ether derivatives compnsmg quaternary
ammonium groups are described in French patent 1 492 5 97. These
polymers are also defined in the CTF A dictionary as quaternary
ammoniums of hydroxyethylcellulose having reacted with an epoxide
10 substituted with a trimethylammonium group.
The cationic cellulose copolymers or the cellulose derivatives
grafted with a water-soluble quaternary ammonium monomer are
described especially m Patent US 4 131 576, such as
hydroxyalkylcelluloses, for instance hydroxymethyl-, hydroxyethyl- or
15 hydroxypropylcelluloses grafted especially with a
methacryloylethyltrimethylammonium, methacrylamidopropyltrimethylammonium
or dimethyldiallylammonium salt.
The cationic galactomannan gums are described more
particularly in Patents US 3 589 578 and 4 031 307, in particular guar
20 gums containing trialkylammonium cationic groups. Use is made, for
example, of guar gums modified with a salt (e.g. chloride) of
2,3-epoxypropyltrimethylammonium.
Other cationic polymers that can be used in the context of the
invention are cationic proteins or cationic protein hydrolysates,
25 polyalkyleneimines, m particular polyethyleneimines, polymers
containing vinyl pyridine or vinylpyridinium units, condensates of
polyamines and of epichlorohydrin, quaternary polyureylenes and
chitin derivatives.
The cationic proteins or protein hydrolysates are, in particular,
30 chemically modified polypeptides bearing quaternary ammomum
groups at the end of the chain, or grafted thereon. Their molecular
mass may vary, for example, from 1500 to 10 000 and in particular
from 2000 to 5000 approximately. Among these compounds, mention
may be made especially of:
5
wo 2011/107467 PCT/EP2011/053013
25
- hydrolysates of collagen bearing triethylammonium groups,
such as the products sold under the name Quat-Pro E by the company
Maybrook and called, m the CTFA dictionary, Triethonium
Hydrolyzed Collagen Ethosulphate;
- hydrolysates of collagen bearing trimethylammonium and
trimethylstearylammonium chloride groups, sold under the name QuatPro
S by the company Maybrook and called, in the CTFA dictionary,
Steartrimonium Hydrolyzed Collagen;
- hydrolysates of animal proteins bearing
10 trimethylbenzylammonium groups, such as the products sold under the
name Crotein BTA by the company Croda and called, in the CTFA
dictionary, Benzyltrimonium hydrolyzed animal protein;
- hydrolysates of proteins bearing, on the polypeptide chain,
quaternary ammonium groups comprising at least one alkyl group
15 containing from 1 to 18 carbon atoms.
20
Among these protein hydrolysates, mention may be made, inter
alia, of:
- Croquat L, the quaternary ammomum groups of which
comprise a cl2 alkyl group;
- Croquat M, the quaternary ammomum groups of which
comprise C1o-C1s alkyl groups;
- Croquat S, the quaternary ammonmm groups of which
comprise a C1s alkyl group;
- Crotein Q, the quaternary ammonmm groups of which
25 comprise at least one alkyl group containing from 1 to 18 carbon
atoms.
30
These various products are sold by the company Croda.
Other quaternized proteins or hydrolysates are, for example,
those corresponding to formula (X):
CH3
I +
R29-N-R3QNH-A
I
CH
3
X-
(X)
wo 2011/107467 PCT/EP2011/053013
26
m which x- is an amon of an orgamc or mineral acid, A
denotes a protein residue derived from collagen protein hydrolysates,
R29 denotes a lipophilic group containing up to 30 carbon atoms, R30
represents an alkylene group containing from 1 to 6 carbon atoms.
5 Mention may, for example, be made of the products sold by the
company Inolex, under the name Lexein QX 3000, called, in the CTFA
dictionary, Cocotrimonium Collagen Hydrolysate.
Mention may also be made of quaternized plant proteins, such
as wheat, corn or soya proteins: as quaternized wheat proteins,
10 mention may be made of those sold by the company Croda under the
names Hydrotriticum WQ or QM, called, in the CTFA dictionary,
Cocodimonium hydrolysed wheat protein, Hydrotriticum QL, called, in
the CTF A dictionary, Laurdimonium hydrolysed wheat protein, or else
Hydrotriticum QS, called, in the CTFA dictionary, Steardimonium
15 hydrolysed wheat protein.
Among all the cationic polymers that may be used in the
context of the present invention, it is preferred to use the cationic
cyclopolymers as defined above, m particular the
dimethyldiallylammonium chloride homopolymers or copolymers sold
20 under the names Merquat 100, Merquat 5 50 and Merquat S by the
company Nalco, quaternary vinylpyrrolidone and vinylimidazole
polymers, cationic polysaccharides and mixtures thereof.
25
The conditioning agent(s) that can be used according to the
invention can be selected from cationic surfactants.
The term "cationic surfactant" means a surfactant which is
positively charged when it is contained in the composition according
to the invention. This surfactant may bear one or more positive
permanent charges or may contain one or more functions that are
cationizable in the composition according to the invention.
30 The cationic surfactant(s) that may be used as conditioning
agents according to the present invention are preferably selected from
primary, secondary or tertiary fatty ammes, optionally
polyoxyalkylenated, or salts thereof, and quaternary ammonium salts,
and mixtures thereof.
5
wo 2011/107467 PCT/EP2011/053013
27
The fatty ammes generally compnse at least one C8-C 30
hydrocarbon-based chain. Among the fatty amines that may be used
according to the invention, examples that may be mentioned include
stearylamidopropyldimethylamine and distearylamine.
Examples of quaternary ammonium salts that may especially be
mentioned include:
- those corresponding to general formula (XI) below:
+
X
(XI)
m which the groups R8 to R11 , which may be identical or
10 different, represent a linear or branched aliphatic group containing
from 1 to 3 0 carbon atoms, or an aromatic group such as an aryl or an
alkylaryl group, at least one of the groups R8 to R11 denoting a group
containing from 8 to 30 carbon atoms, preferably from 12 to 24 carbon
atoms. The aliphatic groups can comprise heteroatoms such as, in
15 particular, oxygen, nitrogen, sulphur and halogens. The aliphatic
groups are, for example, selected from C1-C3o alkyl, C1-C3o alkoxy,
polyoxy(Cz-C6)alkylene, C1-C3o alkylamide,
(Cl2-Cn)alkylamido(Cz-C6)alkyl, (C12-Cn)alkyl acetate and C1-C3o
hydroxyalkyl groups; x- is an anion selected from the group of
20 halides, phosphates, acetates, lactates, (C 1-C4)alkyl sulphates and (C 1-
C4)alkyl or (C 1-C4)alkylaryl sulphonates.
Among the quaternary ammonium salts of formula (XI), those
that are preferred are, on the one hand, tetraalkylammonium salts, for
instance dialkyldimethylammonium or alkyltrimethylammonium salts
25 in which the alkyl group contains approximately from 12 to 22 carbon
30
atoms, m particular behenyltrimethylammonium,
distearyldimethylammonium, cetyltrimethylammonium or
benzyldimethylstearylammonium salts, or, on the other hand, the
palmitylamidopropyltrimethylammonium salt, the
stearamidopropyltrimethylammonium salt, the
wo 2011/107467 PCT/EP2011/053013
28
stearamidopropyldimethylcetearylammonium salt, or the
stearamidopropyldimethyl(myristyl acetate)ammonium salt sold under
the name Ceraphyl® 70 by the company Van Dyk. It is particularly
preferred to use the chloride salts of these compounds;
5 - quaternary ammonium salts of imidazoline, such as, for
example, those of formula (XII) below:
+
(XII)
m which R12 represents an alkenyl or alkyl group containing
from 8 to 30 carbon atoms, for example tallow fatty acid derivatives,
10 R13 represents a hydrogen atom, a C1-C4 alkyl group or an alkenyl or
alkyl group containing from 8 to 30 carbon atoms, R14 represents a C1-
C4 alkyl group, R15 represents a hydrogen atom or a C1-C4 alkyl group,
x- is an anion selected from the group of halides, phosphates, acetates,
lactates, alkyl sulphates, alkyl sulphonates or alkylaryl sulphonates,
15 the alkyl and aryl groups of which preferably comprise, respectively,
from 1 to 20 carbon atoms and from 6 to 30 carbon atoms. Preferably,
R12 and R13 denote a mixture of alkenyl or alkyl groups containing
from 12 to 21 carbon atoms, for example tallow fatty acid derivatives,
R14 denotes a methyl group and R15 denotes a hydrogen atom. Such a
20 product is, for example, sold under the name Rewoquat® W 75 by the
company Rewo;
diquaternary or triquaternary ammonmm salts of formula
(XIII):
wo 2011/107467 PCT/EP2011/053013
29
++ 117 119
R16~-(CH2)s-~-R21 2X
R1s R2o
(XIII)
m which R16 denotes an alkyl group containing from
approximately 16 to 30 carbon atoms, which IS optionally
hydroxylated and/or interrupted with one or more oxygen atoms, R17 is
5 selected from hydrogen or an alkyl group containing from 1 to 4
carbon atoms or the following group:
R'17
I +
R'16-N-(CH2)sl
R'1s YR'
16, R'17, R'1s, R1s, R19, Rzo and Rz1, which may be identical
or different, are selected from hydrogen or an alkyl group containing
10 from 1 to 4 carbon atoms, and x- and y- are anions in particular
selected from the group of halides, acetates, phosphates, nitrates and
(C 1-C6)alkyl sulphates, in particular methyl sulphate or ethyl sulphate.
Such compounds are, for example, Finquat CT -P offered by the
company Finetex (Quaternium-89), Finquat CT offered by the
15 company Finetex (Quaternium 75) and Condicate CT offered by the
company Innospec Active Chemicals (Quaternium-75);
20
- quaternary ammonium salts containing
function, such as those of formula (XIV) below:
0 (CsH2sO)z-R25
II I +
R2~C-(OCrH2r)y -N-(CtH2P)x-R23
I
R22
in which:
at least one ester
X
(XIV)
Rn is selected from C1-C6 alkyl groups and C1-C6 hydroxyalkyl
or dihydroxyalkyl groups;
- R23 is selected from:
5
wo 2011/107467
0
II
R26-c-
the group
PCT/EP2011/053013
30
- the groups R27 which are linear or branched, saturated or
unsaturated C 1-C22 hydrocarbon-based groups,
- a hydrogen atom,
- Rzs is selected from:
0
II
R-c-
the group 28
- the groups R29 which are linear or branched, saturated or
unsaturated C1-C6 hydrocarbon-based groups,
- a hydrogen atom,
10 Rz4, R26 and R28, which may be identical or different, are
15
selected from linear or branched, saturated or unsaturated C7-C21
hydrocarbon-based groups;
r, s and t, which may be identical or different, are integers
ranging from 2 to 6;
y is an integer ranging from 1 to 1 0;
x and z, which may be identical or different, are integers
ranging from 0 to 1 0;
x- is a simple or complex, organic or inorganic anion;
with the proviso that the sum x + y + z is from 1 to 15, that
20 when x is 0, then R23 denotes R27 and that when z is 0, then R25 denotes
The R22 alkyl groups may be linear or branched and more
particularly linear.
Preferably, R22 denotes a methyl, ethyl, hydroxyethyl or
25 dihydroxypropyl group, and more particularly a methyl or ethyl group.
30
Advantageously, the sum x + y + z is from 1 to 10.
When R23 is a hydrocarbon-based group R27 , it may be long and
contain from 12 to 22 carbon atoms, or short and contain from 1 to 3
carbon atoms.
When Rzs IS a hydrocarbon-based group R29, it preferably
wo 2011/107467 PCT/EP2011/053013
31
contains from 1 to 3 carbon atoms.
Advantageously, Rz4, R26 and R28, which may be identical or
different, are selected from linear or branched, saturated or
unsaturated C11 -C21 hydrocarbon-based groups, and more particularly
5 from linear or branched, saturated or unsaturated C11 -C21 alkyl and
alkenyl groups.
10
Preferably, x and z, which may be identical or different, are 0
or 1.
Advantageously, y is equal to 1.
Preferably, r, s and t, which may be identical or different, are
equal to 2 or 3, and even more particularly are equal to 2.
The anion x- is preferably a halide (chloride, bromide or
iodide) or an alkyl sulphate, more particularly methyl sulphate.
However, methanesulphonate, phosphate, nitrate, tosylate, an amon
15 derived from an organic acid, such as acetate or lactate, or any other
20
25
30
anion compatible with the ammonium containing an ester function,
may be used.
The amon x- is even more particularly chloride or methyl
sulphate.
The ammonium salts more particularly used in the composition
according to the invention are the ammonium salts of formula (XIV) in
which:
R22 denotes a methyl or ethyl group,
x and y are qeual to 1;
z is equal to 0 or 1;
r, s and t are equal to 2;
- R23 is selected from:
0
II
R26-c-
the group
-methyl, ethyl or C14-Cn hydrocarbon-based groups,
- a hydrogen atom;
- Rzs is selected from:
wo 2011/107467
0
II
R-c-
the group 28
- a hydrogen atom;
PCT/EP2011/053013
32
Rz4, Rz6 and R28, which may be identical or different, are
selected from linear or branched, saturated or unsaturated C13 -C 17
5 hydrocarbon-based groups, and are preferably from linear or branched,
saturated or unsaturated C13 -C 17 alkyl or alkenyl groups.
The hydrocarbon-based groups are advantageously linear.
Mention may be made, for example, of the compounds of
formula (XIV) such as the diacyloxyethyldimethylammonium,
10 diacyloxyethylhydroxyethylmethylammonium, monoacyloxyethyldihydroxyethylmethylammonium,
triacyloxyethylmethylammonium and
monoacyloxyethylhydroxyethyldimethylammonium salts (chloride or
methyl sulphate in particular), and mixtures thereof. The acyl groups
preferably contain 14 to 18 carbon atoms and are obtained more
15 particularly from a plant oil such as palm oil or sunflower oil. When
the compound contains several acyl groups, these groups may be
identical or different.
These products are obtained, for example, by direct
esterification of triethanolamine, triisopropanolamine, an alkyldi-
20 ethanolamine or an alkyldiisopropanolamine, which are optionally
oxyalkylenated, with C1o-C3o fatty acids or with mixtures of C1o-C3o
fatty acids of plant or animal origin, or by transesterification of the
methyl esters thereof. This esterification IS followed by a
quaternization using an alkylating agent such as an alkyl halide
25 (preferably a methyl or ethyl halide), a dialkyl sulphate (preferably
dimethyl or diethyl sulphate), methyl methanesulphonate, methyl paratoluenesulphonate,
glycol chlorohydrin or glycerol chlorohydrin.
Such compounds are sold, for example, under the names
Dehyquart® by the company Henkel, Stepanquat® by the company
30 Stepan, N oxamium® by the company CECA or Rewoquat® WE 18 by
the company Rewo- Witco.
The composition according to the invention may contain, for
wo 2011/107467 PCT/EP2011/053013
33
example, a mixture of quaternary ammomum salts of mono-, di- and
triesters with a weight majority of diester salts.
Mixtures of ammonium salts that can be used include, for
example, the mixture contammg 15% to 30% by weight of
5 acyloxyethyldihydroxyethylmethylammonium methyl sulphate, 45% to
60% of diacyloxyethylhydroxyethylmethylammonium methyl sulphate
and 15% to 3 0% of triacyloxyethylmethylammonium methyl sulphate,
the acyl groups containing from 14 to 18 carbon atoms and being
obtained from palm oil, which is optionally partially hydrogenated.
10 It is also possible to use the ammonium salts containing at least
one ester function that are described in patents US-A-4874554 and USA-
4137180.
The particularly preferred cationic surfactant(s) that can be
used according to the invention is (are) selected from the compounds
15 of formula (XI) or of formula (XIV), methyl (C9-C 19)alkyl(C 10 -
C20)alkylaminoethylimidazolium salts and stearamidopropyldimethylamine.
Among all the cationic surfactants that may be present in the
composition according to the invention, cetyltrimethylammonium,
20 behenyltrimethylammonium, di(palmitoyloxyethyl)hydroxyethylmethylammonium,
di(stearoyloxyethyl)hydroxyethylmethylammonium
and methyl(C9-C 19 )alkyl(C 1 o-Czo)alkylamidoethylimidazolium salts,
the stearamidopropyltrimethylammonium salt, the stearamidopropyldimethylamine
salt and the stearamidopropyldimethylcetearyl-
25 ammonium salt, and mixtures thereof, are preferably selected.
30
Among the silicones that can be used as conditioning agents in
accordance with the present invention, mention may be made, in a
nonlimiting manner, of:
I. Volatile silicones:
These silicones have a boiling point of between 60°C and
260°C. Among the silicones of this type that are mentioned are:
(a) cyclic silicones containing from 3 to 7 silicon atoms,
and preferably 4 to 5.
These are, for example, octamethylcyclotetrasiloxane sold
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34
under the name Volatile Silicone 7207® by the company Union
Carbide or Silbione 70045 V2® by the company Rh6ne-Poulenc,
decamethylcyclopentasiloxane sold under the name Volatile Silicone
7158® by the company Union Carbide, Silbione 70045 V5® by the
5 company Rh6ne-Poulenc, and mixtures thereof. Mention is also made
of cyclopolymers of the dimethylsiloxane/methylalkylsiloxane type,
such as Volatile Silicone FZ 3109® sold by the company Union
Carbide, which IS a dimethy ls ilo xane/methy lo cty ls ilo xane
cyclopolymer;
10 (b) linear volatile silicones containing 2 to 9 silicon atoms
and having a viscosity of less than or equal to 5x10-6 m2/s at 25°C.
An example is the hexamethyldisiloxane sold under the name
Silbione 70041 V0,65® by the company Rh6ne-Poulenc. This type of
product is described in the article by Todd & Byers "Volatile silicone
15 fluids for cosmetics", Cosmetics and Toiletries, Vol. 91, Jan 76, pages
27 32.
II.Non-volatile silicones
These silicones are mainly constituted by polyalkylsiloxanes,
polyarylsiloxanes polyalkylarylsiloxanes and organomodified
20 polysiloxanes, and mixtures thereof. They may be in the form of oils,
gums and resins.
25
Among the polyalkylsiloxanes, mention may be made mainly of
linear polydimethylsiloxaneS with a ViSCOSity Of greater than 5 X 1 o-6
m2 /s, and preferably less than2.6 m2 /s, i.e.:
- containing trimethylsilyl end groups, for instance, and in a
nonlimiting manner, the Silbione® oils of the 70047 series sold by the
company Rh6ne-Poulenc, the Wacker Belsil DM 60000 oil from
Wacker or certain Viscasil® from the company General Electric,
- containing trihydroxysilyl end groups, such as the oils of the
30 48 V® series from the company Rh6ne-Poulenc.
In this class of polyalkylsiloxanes, mention may also be made
of the polyalkylsiloxanes sold by the company Goldschmidt under the
names Abil Wax 9800® and Abil Wax 9801 ®, which are
poly(CI-zo)alkylsiloxanes.
5
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35
Among the polyalkylarylsiloxanes, mention may be made of
linear and/or branched polydimethylphenylsiloxanes and
polydimethyldiphenylsiloxanes, with a viscosity from 1 o-S to
5 X 1 o-l m2/S, for instance:
- the oil Rhodorsil® 763 from Rh6ne-Poulenc,
- the Silbione® oils of the 70641 series from Rh6ne-Poulenc,
such as the oils Silbione 70641 V30® and Silbione 70641 V200®,
- the product DC 556® Cosmetic Grade Fluid from Dow
Corning,
10 - the silicones of the PK series from Bayer, such as PK20®,
- the silicones of the PN and PH series from Bayer, such as the
products PN 1 000® and PH 1 000®;
- certain oils of the SF series from General Electric, such as SF
1250®, SF 1265®, SF 1154® and SF 1023®.
15 The silicone gums in accordance with the present invention are
polydiorganosiloxanes with a high number-average molecular mass of
between 200 000 and 1 000 000, used alone or as a mixture in a
solvent selected from volatile silicones, polydimethylsiloxane (PDMS)
oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffins, methylene
20 chloride, pentane, dodecane, tridecane and tetradecane, or mixtures
thereof.
Mention is made, for example, of the compounds having the
following structures:
- poly[ ( dimethylsiloxane )/(methylvinylsiloxane)] gums,
25 - poly[ ( dimethylsiloxane )/( diphenylsiloxane)] gums,
30
- poly[ ( dihydrogenodimethylsiloxane )/( divinylsiloxane)] gums,
- poly[ ( dimethylsiloxane )/(phenylmethylsiloxane)] gums,
- poly[ ( dimethy lsiloxane )/( diphenylsiloxane )/ (methylvinylsiloxane)]
gums.
The Mirasil DM 300 000 gum from the company Rhodia may be
mentioned.
Mention may also be made, for example, in a nonlimiting
manner, of the following mixtures:
1) mixtures formed from a polydimethylsiloxane hydroxylated
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at the end of the chain ( dimethiconol according to the CTF A
nomenclature), and from a cyclic polydimethylsiloxane
( cyclomethicone according to the CTF A nomenclature), such as the
products Q2 1401® or Dow Corning 1501 Fluid sold by the company
5 Dow Corning;
2) mixtures formed from a polydimethylsiloxane gum with a
cyclic silicone, such as the product SF 1214 Silicone Fluid® from
General Electric, which is an SE 30® gum of MW 500 000 ( -Mn)
dissolved in SF 1202 Silicone Fluid® (decamethylcyclopentasiloxane);
10 3) mixtures of two PDMSs of different viscosities, especially
of a PDMS gum and a PDMS oil, such as the products SF 1236® and
CF 1241® from the company General Electric. The product SF 1236®
is a mixture of an SE 30® gum defined above, with a viscosity of
20 m2/s, and of an SF 96® oil with a viscosity of 5x106 m2/s (15%
15 SE 30® gum and 85% SF 96® oil).
The product CF 1241® is a mixture of an SE 30® gum (33%)
and of a PDMS (67%), with a viscosity of 10-3 m2/s.
The organopolysiloxane resins that may be used m accordance
with the invention are crosslinked siloxane systems containing the
20 following units: R2Si0212 , RSi0312 and Si0412 in which R represents a
hydrocarbon-based group containing 1 to 6 carbon atoms or a phenyl
group. Among these products, those which are particularly preferred
are those in which R denotes a (C 1-C4 ) lower alkyl group or a phenyl
group.
25 Among these resins, mention may be made of the product sold
under the name Dow Corning 593® or those sold under the names
Silicone Fluid SS 4230 and Silicone Fluid SS 4267 by the company
General Electric and which are dimethyl/trimethylpolysiloxanes.
The organomodified silicones in accordance with the present
30 invention are silicones as defined above, comprising, in their general
structure, one or more organofunctional groups directly attached to the
siloxane chain or attached by means of a hydrocarbon-based group.
Mention is made, for example, of the silicones comprising:
a) perfluoro groups such as trifluoroalkyls, for instance those
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sold by the company General Electric under the names FF .150
Fluorosilicone Fluid® or by the company Shin-Etsu under the names
X-22-819®, X-22-82®, X-22-821 ® and X-22-822®;
b) hydroxyacylamino groups, for instance those described in
5 patent application EP 0 342 834 and in particular the silicone sold by
the company Dow Corning under the name Q2-8413®;
c) thiol groups, as in the silicones X 2-8360® from the
company Dow Corning or GP 72A® and GP 71® from Genesee;
d) non-quaternized amino groups, such as GP 4 Silicone Fluid®
10 from Genesee, GP 71 00® from Genesee, Q2 8220® from Dow Corning,
AFL 40® from umon Carbide or the silicone known as
Amodimethicone in the CTFA dictionary;
e) carboxylate groups, for instance the products described in
patent EP 186 507 from Chisso Corporation;
15 f) hydroxylated groups, such as polyorganosiloxanes
comprising a hydroxyalkyl function, described in Patent Application
FR 85 163 34, corresponding to formula (XV) below:
(R1h-Si
p
(XV)
in which:
20 - the R1 groups, which may be identical or different, are
25
selected from methyl and phenyl groups, at least 60 mol% of the R1
groups being methyl;
-the R' 1 group is a divalent hydrocarbon-based C2-C 18 alkylene
link;
- p is between 1 and 30 inclusive;
- q is between 1 and 150 inclusive.
Mention may most particularly be made of the product sold by
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38
Dow Corning under the name DC 190;
g) alkoxylated groups, for instance in the silicone copolymer F
755® from SWS Silicones and the products Abil Wax 2428®, Abil
Wax 2434® and Abil Wax 2440® from the company Goldschmidt;
5 h) acyloxyalkyl groups, for instance the
polyorganopolysiloxanes described in Patent Application FR 88 17433,
corresponding to formula (XVI) below:
R' R' R' I 2 I 2 I 2
(R2)3-Si 0-Si------l-+-0-Si-+----t-0- Sl' 0 - SI'(R2)3
I I I I r R'2
OCOR" OH
p q (XVI)
in which:
10 - R2 denotes methyl, phenyl, OCOR" or hydroxyl, it being
possible for only one of the R2 per silicon atom to be OH;
- R' 2 denotes methyl or phenyl, at least 60 mol% of the R2 and
R' 2 groups together being methyl;
- R" denotes Cs-Czo alkyl or alkenyl;
15 - R denotes a divalent, linear or branched C2-C 18 hydrocarbonbased
alkylene;
- r is between 1 and 120 inclusive;
- p is between 1 and 30 inclusive;
- q is equal to 0 or is less than 0.5 p, p + q being between 1
20 and 30 inclusive;
the polyorganosiloxanes of formula (XVI) can comprise:
CH-Si-OH
3 I
0 2; 2
groups in proportions not exceeding 15% of the sump + q + r;
25 i) quaternary ammonium groups, as in the products X2 81 08®
and X2 81 09® and the product Abil K3270® from the company
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39
Goldschmidt;
j) amphoteric or betaine groups, as in the product sold by the
company Goldschmidt under the name Abil B 9950®;
k) bisulfite groups, as in the products sold by the company
5 Goldschmidt under the names Abil S 201 ® and Abil S 255®;
1) polyethyleneoxy and/or polypropyleneoxy groups optionally
compnsmg C6-C24 alkyl groups, such as the products called
dimethicone copolyol, sold by the company Dow Corning under the
name DC 1248, or the oils Silwet L 722, L 7500, L 77 and L 711 from
10 the company Union Carbide, and the (C 12)alkyl methicone copolyol
sold by the company Dow Corning under the name Q2 5200.
According to the invention, use may also be made of silicones
comprising a polysiloxane portion and a portion consisting of a nonsilicone
organic chain, one of the two portions constituting the main
15 chain of the polymer, the other being grafted onto said main chain.
These polymers are, for example, described in patent applications
EP-A-412 704, EP-A-412 707, EP-A-640 105, WO 95/00578,
EP-A-5 82 152 and WO 93/23009 and patent applications
US 4,693,935, US 4,728,571 and US 4,972,037. These polymers are
20 preferably anionic or non-ionic.
25
Such polymers are, for example, copolymers that may be
obtained by radical polymerization from the monomer mixture formed
from:
a) 50% to 90% by weight of tert-butyl acrylate;
b) 0 to 40% by weight of acrylic acid;
c) 5% to 40% by weight of silicone macromer of formula
(XVII):
0 CH3
II I
H C==C-C-0-(CH) -Si-0
2 I 2 3 1
CH3 CH3
(XVII)
with v being a number ranging from 5 to 700; the percentages
30 by weight being calculated relative to the total weight of the
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40
monomers.
Other examples of grafted silicone polymers are, in particular,
polydimethylsiloxanes (PDMSs) onto which are grafted, by means of a
connecting link of thiopropylene type, mixed polymer units of the
5 poly((meth)acrylic acid) type and of the poly(alkyl (meth)acrylate)
type; and polydimethylsiloxanes (PDMSs) onto which are grafted, by
means of a connecting link of thiopropylene type, polymer units of the
poly( isobutyl (meth)acrylate) type.
According to the invention, all the silicones can also be used in
10 the form of emulsions, nanoemulsions or microemulsions.
The polyorganosiloxanes which are particularly preferred m
accordance with the invention are:
non-volatile silicones selected from the family of
polyalkylsiloxanes with trimethylsilyl end groups, such as oils having
15 a viscosity of between 0.2 and 2.5 m2/s at 25°C, for instance the oils
of the DC200 series from Dow Corning, in particular the one with a
viscosity of 60 000 eSt, or of the Silbione 7004 7 and 4 7 series, and
more particularly the oil 70 04 7 V 5 00 000 sold by the company
Rhodia Chimie, and polyalkylsiloxanes with dimethylsilanol end
20 groups, such as dimethiconols or polyalkylarylsiloxanes, for instance
the oil Silbione 70641 V 200 sold by the company Rhodia Chimie;
- polysiloxanes with amino groups, such as amodimethicones
and trimethylsilyl amodimethicones.
The viscosities of the silicones may especially be determined
25 by the standard ASTM D445-97 (viscometry).
When the conditioning agent of the composition according to
the invention is a hydrocarbon, said hydrocarbon is a linear or
branched Cs-C3o hydrocarbon.
Among the hydrocarbons which are liquid at ambient
30 temperature and which correspond to this definition, mention may in
particular be made of isododecane, isohexadecane and its isomers
(such as 2,2,4,4,6,6-heptamethylnonane), isoeicosane, isotetracosane,
the Isomers of said compounds, n-nonadecane, n-dodecane,
n-undecane, n-tridecane, n-pentadecane, and mixtures of these
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41
hydrocarbons.
Use IS preferably made according to the invention of
isododecane or an isomer thereof.
When the conditioning agent IS a fatty alcohol, said fatty
5 alcohol is of the linear or branched, saturated or unsaturated C8 -
C30 type. Among the latter, mention may, for example, be made of 2-
butyloctanol, lauryl alcohol, 2-octyldodecanol, oleyl alcohol, isocetyl
alcohol, isostearyl alcohol and behenyl alcohol, and mixtures thereof.
When the conditioning agent is a fatty ester, said fatty ester
10 may be either an ester of a Cs-C3o fatty acid and of a C1-C3o alcohol,
and in particular an ester of a C8-C30 fatty acid and of a C8-C30 fatty
alcohol, or an ester of a C1-C7 acid or diacid and of a Cs-C3o fatty
alcohol.
Among these esters, mention may, for example, be made of
15 ethyl, isopropyl, 2-ethylhexyl and 2-octyldecyl palmitate, isopropyl,
butyl, cetyl and 2-octyldecyl myristate, butyl and hexyl stearate, hexyl
and 2-hexyldecyl laurate, isononyl isononanoate, dioctyl malate,
myristyl myristate and cetyl palmitate, and mixtures thereof.
The ceramides or ceramide analogues, such as glycoceramides,
20 that can be used as conditioning agent in the compositions according
to the invention are known in themselves and are natural or synthetic
molecules that can correspond to general formula (XVIII) below:
in which:
R3CHOH-CH-CH20R I 2
NH
I
c=o
I
R1 (XVIII)
25 - R1 denotes a linear or branched, saturated or unsaturated
alkyl group, derived from C14-C30 fatty acids, it being possible for this
group to be substituted with a hydroxyl group in the alpha-position, or
a hydroxyl group in the omega-position esterified with a saturated or
unsaturated C16-C3o fatty acid;
wo 2011/107467 PCT/EP2011/053013
42
- R2 denotes a hydrogen atom or a (glycosyl)n, (galactosyl)m or
sulphogalactosyl group, in which n is an integer ranging from 1 to 4
and m is an integer ranging from 1 to 8;
- R3 denotes a C1s-C26 hydrocarbon-based group, saturated or
5 unsaturated in the alpha-position, it being possible for this group to be
substituted with one or more C 1-C 14 alkyl groups;
it being understood that, in the case of natural ceramides or
glycoceramides, R3 can also denote a C 15 -C26 alpha-hydroxyalkyl
group, the hydroxyl group being optionally esterified with a C16-C30
10 alpha-hydroxy acid.
15
20
The ceramides which are preferred in the context of the present
invention are those described by Downing in Arch. Dermatol.,
Vol. 123, 1381-1384, 1987, or those described in French patent
FR 2 673 179.
The ceramide(s) more particularly preferred according to the
invention is (are) the compounds for which R1 denotes a saturated or
unsaturated alkyl derived from C16-C22 fatty acids; R2 denotes a
hydrogen atom; and R3 denotes a linear, saturated C15 group.
Such compounds are, for example:
- N-linoleoyldihydrosphingosine,
- N -oleoyldihydrosphingosine,
- N -palmitoyldihydrosphingosine,
- N -stearoyldihydrosphingosine,
- N-behenoyldihydrosphingosine,
25 or mixtures of these compounds.
30
Even more preferably, ceramides for which R1 denotes a
saturated or unsaturated alkyl group derived from fatty acids; R2
denotes a galactosyl or sulphogalactosyl group; and R3 denotes a
-CH=CH-(CHz)12-CH3 group, are used.
By way of example, mention may be made of the product
consisting of a mixture of these compounds, sold under the trade name
Glycocer by the company Waitaki International Biosciences.
Among all these conditioning agents, use is preferably made of
one or more conditioning agents selected from silicones such as
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43
organosiloxanes and cationic polymers.
The cosmetic composition according to the invention preferably
contains from 0.01% to 20% by weight, and more preferably from
0.05% to 10% by weight of conditioning agent(s) relative to the total
5 weight of the composition.
The composition according to the invention may also comprise
at least one additional surfactant selected from non-ionic surfactants.
Examples of non-ionic surfactants that can be used in the
composition used according to the invention are described, for
10 example, in "Handbook of Surfactants" by M.R. PORTER, published
by Blackie & Son (Glasgow and London), 1991, pp. 116-178. They are
selected in particular from alcohols, alpha-diols, (C 1_ 20)alkylphenols
or polyethoxylated, polypropoxylated and/or polyglycerolated fatty
acids having a fatty chain containing, for example, from 8 to 18 carbon
15 atoms, it being possible for the number of ethylene oxide and/or
propylene oxide groups to range in particular from 2 to 50 and it being
possible for the number of glycerol groups to range in particular from
2 to 30.
Mention may also be made of copolymers of ethylene oxide and
20 of propylene oxide, optionally oxyethylenated fatty acid esters of
sorbitan, fatty acid esters of sucrose, polyoxyalkylenated fatty acid
esters, optionally oxyalkylenated alkylpolyglycosides, alkylglucoside
esters, N -alkylglucamine and N -acylmethylglucamine derivatives,
aldo bionamides and amine oxides.
25 Unless otherwise mentioned, the term "fatty" compound (for
example a fatty acid) denotes a compound comprising, in its main
chain, at least one saturated or unsaturated alkyl chain containing at
least 8 carbon atoms, preferably from 8 to 30 carbon atoms, and even
better still from 10 to 22 carbon atoms.
30 When they are present, the amount of the non-wmc
surfactant(s) preferably ranges from 0.01% to 20 % by weight and
better still from 0.2% to 10 % by weight relative to the total weight of
the composition.
Advantageously, the total content of anionic and amphoteric or
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44
zwitterionic surfactant(s ), and optionally non-ionic surfactant(s ), when
it (they) is (are) present in the composition according to the invention,
ranges from 4% to 50% by weight, and better still from 4% to 30% by
weight, and more particularly from 10% to 20% by weight, relative to
5 the total weight of the composition according to the invention.
The composition according to the invention is generally used in
topical application.
In particular, the composition according to the invention may
be in any galenical form normally used for topical application. The
10 composition according to the invention may be a rinse-out or leave-in
composition. In particular, it may be a shampoo, a cream, a gel or an
emulsion. Preferably, the composition according to the invention is a
shampoo.
The composition according to the invention compnses a
15 cosmetically acceptable medium. The medium consists of water and
optionally of one or more cosmetically acceptable organic solvents.
The organic solvent(s) may be selected from C1-C4 lower
alcohols, such as ethanol, isopropanol, tert-butanol or n-butanol;
polyols, such as glycerol, propylene glycol, hexylene glycol (or
20 2-methyl-2,4-pentanediol) and polyethylene glycols; polyol ethers, for
instance dipropylene glycol monomethyl ether; and mixtures thereof.
When the medium compnses at least one cosmetically
acceptable organic solvent, said solvent may be present in a proportion
of from 0.1% to 30% by weight, preferably from 0.2% to 15% by
25 weight, of the total weight of the composition.
30
The cosmetic composition according to the invention may have
a pH of between 3 and 10 and preferentially between 5 and 7. This pH
may be adjusted by means of acidifying and basifying agents
conventionally used in cosmetics.
The cosmetic composition used according to the invention may
also contain one or more adjuvants that are customary in the cosmetics
field, such as agents for preventing hair loss, oxidizing agents,
vitamins and provitamins, including panthenol, plant, animal, mineral
or synthetic oils, waxes, sunscreens, coloured or uncoloured, mineral
5
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45
or orgamc pigments, dyes, pearlescent agents and opacifiers,
sequestering agents, plasticizers, solubilizing agents, antioxidants,
hydroxy acids, fragrances, anti-dandruff agents other than the
compounds (i) as defined above, preservatives, and mixtures thereof.
The amounts of these vanous adjuvants are those
conventionally used in the fields under consideration.
Of course, those skilled in the art will take care to select the
optional compound(s) to be added to the composition according to the
invention in such a way that the advantageous properties intrinsically
10 associated with the composition in accordance with the invention are
not, or not substantially, impaired by the addition(s) envisaged.
Another subject of the invention consists of a cosmetic
treatment method for the scalp and for keratin fibres, in particular
human keratin fibres such as the hair, comprising the application of a
15 composition according to invention to the scalp and said keratin fibres.
After an optional pause time preferably ranging from 1 to 15 minutes,
the composition is then preferably rinsed out with water. Said method
is preferably intended for washing said keratin fibres and/or for antidandruff
treatment intended for eliminating and/or reducing dandruff,
20 and in particular dandruff caused by yeasts of the Malassezia genus.
A subject of the invention is also the use of a composition
according to the invention for washing keratin fibres, in particular
human keratin fibres such as the hair.
A subject of the invention is also the use of a composition
25 according to the invention for anti-dandruff treatment intended for
eliminating and/or reducing dandruff, and in particular dandruff
caused by yeasts of the Malassezia genus.
30
The examples which follow are intended to illustrate the
invention without, however, being limiting in nature.
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46
EXAMPLES:
Example 1: Shampoo
5 The following composition was prepared. The amounts are
indicated as per cent by weight of active material (A.M.) relative to
the total weight of the composition.
Composition
% by weight of
A.M.
Fragrance 0.5
Coconut acid monoisopropanolamide
(Empilan CIS sold by the company 0.25
Huntsman)
Cocoylamidopropylbetaine at 38% by weight
in an aqueous solution (Tego betain F50 sold 2.4
by the company Evonik Goldschmidt)
Sodium lauryl ether sulphate containing
2.2 mol of ethylene oxide, at 26% by weight
15.5
in an aqueous solution (Texapon AOS 225 UP
sold by the company Cognis)
Ellagic acid 1
Sodium benzoate 0.5
Salicylic acid 0.2
Polydimethylsiloxane 500 000 eSt (molecular
weight 250 000) (Silbione 70047 V500000 2
sold by the company Bluestar)
1-(Hexadecyloxy)-2-octadecano 11 cetyl
alcohol mixture (Mexanyl GY sold by the 2.5
company Chimex)
Carboxyvinyl polymer (Carbopol 980 sold by
0.3
the company Lubrizol)
Propylene glycol 0.1
5
wo 2011/107467 PCT/EP2011/053013
47
Glycerol 2
Sodium chloride 1.1
pH agents qspH5.3
Fragrance Qs
Water qs 100
The shampoo obtained has the appearance of a viscous opaque
beige liquid, and is characterized by a fine dispersion of the ellagic
acid and is stable over time.
Applied to the hair and the scalp and then rinsed out, the
shampoo exhibits good usage qualities (easy to apply, pleasant and
soft foam, easy to remove), promoting distribution of the ellagic acid
on the scalp while at the same time exhibiting good cosmetic
effectiveness on the hair (softness, smoothing) associated with good
10 detergence.
15
Anti-dandruff effectiveness is good, in particular with repeated
application.
Example 2: Shampoo
The following composition was prepared. The amounts are
indicated as per cent by weight of active material (A.M.) relative to
the total weight of the composition.
Composition
% by weight of
A.M.
Polydimethylsiloxane (Belsil DM 60 000 sold
0.7
by the company Wacker)
Coconut acid monoisopropanolamide
(Empilan CIS sold by the company 0.5
Huntsman)
Cocoylbetaine at 30% by weight in an
1.8
aqueous solution (Dehyton AB 30 sold by the
5
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48
company Cognis)
Carboxyvinyl polymer (Carbopol 980 sold by
0.2
the company Lubrizol)
Hydroxypropyl guar trimethylammonium
chloride (Jaguar C 13-S sold by the company 0.03
Rhodia)
Ellagic acid 1
Ethylene glycol distearate 1.6
Salicylic acid 0.2
Sodium benzoate 0.5
Sodium lauryl ether sulphate containing
2.2 mol of ethylene oxide, at 26% by weight
12.2
in an aqueous solution (Texapon AOS 225 UP
sold by the company Cognis)
Hexylene glycol (2-methyl-2,4-pentanediol) 0.5
Sodium chloride 1.5
pH agents qspH5.3
Fragrance Qs
Water qs 100
The shampoo obtained has the appearance of a viscous opaque
beige liquid, and is characterized by a fine dispersion of the ellagic
acid and is stable over time.
Applied to the hair and the scalp and then rinsed out, this
shampoo exhibits good usage qualities (easy to apply, pleasant and
soft foam, easy to remove), promoting distribution of the ellagic acid
on the scalp while at the same time exhibiting good cosmetic
effectiveness on the hair (softness, smoothing) associated with good
10 detergence.
Anti-dandruff effectiveness is good, in particular with repeated
application.
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49
Example 3: Shampoo
The following composition was prepared. The amounts are
indicated as per cent by weight of active material relative to the total
5 weight of the composition.
10
Composition
% by weight of
A.M.
Sodium lauryl sulphate 6.75
Sodium lauryl ether sulphate containing
8.25
2.2 mol of ethylene oxide
Glycerol 2
Sodium chloride 1.2
Ellagic acid 1
Ethylene glycol distearate 1
Salicylic acid 0.2
Coconut acid monoisopropanolamide
2
(Comperlan 100 sold by the company Cognis)
Polydimethylsiloxane (Mirasil DM 300 000
0.4
sold by the company Rhodia)
Sodium benzoate 0.5
Hydroxypropyl guar trimethylammonium
chloride (Jaguar C 13-S sold by the company 0.05
Rhodia)
Carboxyvinyl polymer (Carbopol 980 sold by
0.3
the company Lubrizol)
Fragrance, dye qs
Water qs 100
The shampoo obtained exhibits a fine dispersion of the ellagic
acid and is stable over time.
Applied to the hair and the scalp, this shampoo exhibits good
usage qualities (easy to use, pleasant and soft foam, easy to remove),
5
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50
promoting distribution of the ellagic acid on the hair and the scalp
while at the same time exhibiting good cosmetic effectiveness
(softness, smoothing) associated with the good detergence. Antidandruff
effectiveness is good, in particular with repeated application.

CLAIMS
1. Cosmetic composition compnsmg, m a cosmetically
acceptable medium:
(i) from 0.2% to 10% by weight of one or more compounds
selected from ellagic acid, ethers thereof, ellagic acid salts and ellagic
5 acid ether salts, and mixtures thereof, and
(ii) a system of surfactants selected from the following
mixtures comprising:
- (iii) one or more amomc surfactants selected from
ethoxylated alkyl sulphates, the corresponding acids, and mixtures
10 thereof, and (iv) one or more anionic surfactants different from the
abovementioned anionic surfactant(s) (iii), and
- (v) one or more anionic surfactants and (vi) one or more
amphoteric or zwitterionic surfactants, in a weight ratio of the amount
of anionic surfactant(s) to the amount of amphoteric or zwitterionic
15 surfactant(s) of greater than 3.
2. Composition according to Claim 1, characterized in that the
salt(s) of the compound (i) is (are) selected from the alkali metal or
alkaline-earth metal salts, in particular the sodium, potassium, calcium
or magnesium salts.
20 3. Composition according to Claim 1 or 2, characterized in that
the ellagic acid ether(s) is (are) chosen from mono-, di-, tri- or
polyethers obtained by etherification of one or more hydroxyl groups
of ellagic acid to give one or more OR groups, R being selected from
C2-C20 alkyl groups, polyoxyalkylene groups, and in particular
25 polyoxyethylene and/or polyoxypropylene groups, and groups derived
from one or more monosaccharides or polysaccharides.
4. Composition according to Claim 1 or 2, characaterized
in that the compound (i) is ellagic acid or a salt thereof.
5. Composition according to any one of the preceding claims,
30 characterized in that it comprises from 0.2% to 5% by weight, and
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52
even better still from 0.2% to 2% by weight of compound(s) (i),
relative to the total weight of the composition.
6. Composition according to any one of Claims 1 to 5,
characterized in that the anionic surfactant(s) (iii) is (are) selected
5 from ethoxylated (C6-C24)alkyl sulphates comprising from 1 to
50 mol of ethylene oxide, preferably from 1 to 10 mol, in particular
from 1 to 5 mol, and even better still from 2 to 3 mol.
7. Composition according to the preceding claim,
characterized in that it comprises from 0.1% to 50% by weight, m
10 particular from 2% to 20% by weight, even better still from 4% to
15% by weight, and even better still from 5% to 15% by weight of
anionic surfactant(s) (iii), relative to the total weight of the
composition.
8. Composition according to any one of Claims 1 to 5,
15 characterized in that the anionic surfactant(s) (iv) different from the
anionic surfactants (iii) is (are) selected from nonethoxylated alkyl
sulphates, alkylamido ether sulphates, alkylaryl polyether sulphates,
monoglyceride sulphates, alkyl sulphonates, alkylamide sulphonates,
alkylarylsulphonates, alpha-olefin sulphonates, paraffin sulphonates,
20 alkylsulphosuccinates, alkyl ether sulphosuccinates, alkylamide
sulphosuccinates, alkyl sulphoacetates, acylsarcosinates,
acylglutamates, alkyl sulphosuccinamates, acyl isethionates and Nacyltaurates;
salts of alkyl monoesters of polyglycosidepolycarboxylic
acids, acyllactylates, salts of D-galactosiduronic
25 acids, salts of alkyl ether carboxylic acids, salts of alkyl aryl ether
carboxylic acids, salts of alkylamido ether carboxylic acids; and the
corresponding non-salified forms of all these compounds; the alkyl
and acyl groups of all these compounds containing from 6 to
24 carbon atoms and the aryl group denoting a phenyl group.
30 9. Composition according to the preceding claim,
characterized in that it comprises from 0.1% to 30% by weight, in
particular from 1% to 20% by weight, and even better still from 2%
to 15% by weight of anionic surfactant(s) (iv).
10. Composition according to any one of the preceding
5
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claims, characterized in that the weight ratio of the amount of anionic
surfactant(s) (iii) to the amount of anionic surfactant(s) (iv) ranges
from 0.25 to 20, preferably from 0.5 to 10, better still from 1 to 5,
and even better still from 1 to 2.5.
11. Composition according to any one of Claims 1 to 5,
characterized in that the anionic surfactant(s) (v) is (are) selected
from alkyl sulphates, alkyl ether sulphates, alkylamido ether sulphates,
alkylaryl polyether sulphates, monoglyceride sulphates, alkyl
sulphonates, alkylamide sulphonates, alkylarylsulphonates, alpha-olefin
10 sulphonates, paraffin sulphonates, alkylsulphosuccinates, alkyl ether
sulphosuccinates, alkylamide sulphosuccinates, alkyl sulphoacetates,
acylsarcosinates, acylglutamates, alkyl sulphosuccinamates, acyl
isethionates and N-acyltaurates; salts of alkyl monoesters of
polyglycoside-polycarboxylic acids, acyllactylates, salts of
15 D-galactosiduronic acids, salts of alkyl ether carboxylic acids, salts of
alkyl aryl ether carboxylic acids, salts of alkylamido ether carboxylic
acids; and the corresponding non-salified forms of all these compounds;
the alkyl and acyl groups of all these compounds containing from 6 to
24 carbon atoms and the aryl group denoting a phenyl group.
20 12. Composition according to the preceding claim,
characterized in that it comprises from 0.1% to 50% by weight, in
particular from 4% to 30% by weight, and even better still from 8%
to 20% by weight of anionic surfactant(s) (v).
13. Composition according to any one of the preceding
25 claims, characterized m that the amphoteric or zwitterionic
surfactant(s) (vi) IS (are) selected from (C 8_ 20 )alkylbetaines,
sulpho betaines, (C 8 _20 alkyl)amido(C 2_8 alkyl)betaines, and
(C 8 _20 alkyl)amido(C2_8 alkyl)sulpho betaines and preferably from
(Cs-2o alkyl)betaines, and (Cs-2o alkyl)amido(C2-s alkyl)betaines.
30 14. Composition according to any one of Claims 1 to 12,
characterized in that the amphoteric or zwitterionic surfactant(s) (vi)
is (are) selected from the compounds of respective structures (A2)
and (A3) below:
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54
in which:
Ra represents a C10-C30 alkyl or alkenyl group derived from an acid
Ra-COOH preferably present in hydrolysed coconut oil, a heptyl group,
5 a nonyl group or undecyl group,
10
Rb represents a beta-hydroxyethyl group, and
Rc represents a carboxymethyl group;
and
Ra·-CONHCHzCHz-N(B)(B')
in which:
B represents -CHzCHzOX',
B' represents -(CH2 )z-Y', with z = 1 or 2,
(A3)
X' represents the -CHz-COOH, CHz-COOZ', -CHzCHz-COOH or
15 -CH2CH2-COOZ' group, or a hydrogen atom,
Y' represents -COOH, -COOZ', or the -CH2-CHOH-S03H or
-CHz-CHOH-S03Z' group,
Z' represents an ion derived from an alkali or alkaline-earth metal,
such as sodium, potassium or magnesium; an ammonium ion; or an ion
20 derived from an organic amine and in particular from an aminoalcohol,
such as monoethanolamine, diethanolamine and triethanolamine,
monoisopropanolamine, diisopropanolamine or triisopropanolamine, 2-
amino-2-methyl-1-propanol, 2-amino-2-methyl-1 ,3 -propanedio 1 and
tris(hydroxymethyl)aminomethane.
25 Ra· represents a C1o-C3o alkyl or alkenyl group of an acid Ra·COOH
preferably present in hydrolysed linseed oil or coconut oil, an alkyl
group, which is in particular C17 , and its ISO form, or an unsaturated
cl7 group.
15. Composition according to any one of the preceding
30 claims, characterized in that it comprises from 0.01% to 20% by
weight, in particular from 0.5% to 10% by weight, and even better
still from 1% to 5% by weight of amphoteric or zwitterionic
surfactant(s) (vi), relative to the total weight of the composition.
16. Composition according to any one of the preceding
5
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claims, characterized in that it comprises one or more thickeners
and/or one or more conditioning agents preferably selected from
silicones and cationic polymers, and/or one or more additional
surfactants selected from non-ionic surfactantso
17 0 Cosmetic treatment method, characterized m that it
comprises the application of a cosmetic composition as defined m
any one of Claims 1 to 16 to the scalp and to keratin fibres, m
particular human keratin fibres such as the hair.
18 0 Use of a cosmetic composition as defined in any one of
10 Claims 1 to 16 for washing keratin fibres, in particular human keratin
fibres such as the hair.