Cosmetic Composition Comprising at Least One Electrophilic Monomer, at least One Fluoro Compound and at Least One Liquid Organic Solvent
Cosmetic Composition Comprising at Least One Electrophilic Monomer, at least One Fluoro Compound and at Least One Liquid Organic Solvent
US20080038218
Folder:
Year:
Abstract:
The present disclosure relates to a cosmetic composition for treating keratin fibers, for instance human keratin fibers such as the hair, comprising at least one liquid organic solvent, at least one electrophilic monomer and at least one organofluorine compound comprising at least 4 carbon atoms, with the exception of polytetrafluoroethylene, and pigments coated with fluoro compounds.
Language:
(19) United States
US 200800382l8Al
(12) Patent Application Publication (10) Pub. No.: US 2008/0038218 A1
Brun et al.
(43) Pub. Date: Feb. 14, 2008
(54) COSMETIC COMPOSITION COMPRISING
AT LEAST ONE ELECTROPHILIC
MONOMER, AT LEAST ONE FLUORO
COMPOUND AND AT LEAST ONE LIQUID
ORGANIC SOLVENT
(76) Inventors: Gaelle Brun, Paris (FR); Aude
Livoreil, Paris (FR)
Correspondence Address:
FINNEGAN, HENDERSON, FARABOW,
GARRETT & DUNNER
LLP
901 NEW YORK AVENUE, NW
WASHINGTON, DC 20001-4413 (US)
(21) Appl. No.: 11/784,000
(22) Filed: Apr. 13, 2007
Related U.S. Application Data
(60) Provisional application No. 60/796,218, filed on May
1, 2006.
(30) Foreign Application Priority Data
Apr. 13, 2006 (FR) .......................................... .. 06/03281
Publication Classification
(51) Int. Cl.
A61K 8/72 (2006.01)
A61Q 5/00 (2006.01)
(52) U.S.Cl. ................................... .. 424/70.16;424/70.11
(57) ABSTRACT
The present disclosure relates to a cosmetic composition for
treating keratin fibers, for instance human keratin fibers such
as the hair, comprising at least one liquid organic solvent, at
least one electrophilic monomer and at least one organof-
luorine compound comprising at least 4 carbon atoms, with
the exception of polytetrafluoroethylene, and pigments
coated with fluoro compounds.
US 2008/0038218 A1
COSMETIC COMPOSITION COMPRISING AT
LEAST ONE ELECTROPHILIC MONOMER, AT
LEAST ONE FLUORO COMPOUND AND AT
LEAST ONE LIQUID ORGANIC SOLVENT
[0001] This application claims benefit of U.S. Provisional
Application No. 60/796,218, filed May 1, 2006, the contents
of which are incorporated herein by reference. This appli-
cation also claims benefit of priority under 35 U.S.C. § 119
to French Patent Application No. FR 06/ 03281, filed Apr. 13,
2006, the contents of which are also incorporated herein by
reference.
[0002] The present disclosure relates to a cosmetic com-
position for treating keratin fibers, for instance human
keratin fibers such as the hair, comprising at least one
electrophilic monomer, at least one particular organofluorine
compound and at least one liquid organic solvent, to a use of
this composition for treating the hair and also to a treatment
process involving the composition as disclosed herein.
[0003] Hair is generally damaged and embrittled by the
action of external atmospheric agents such as the light and
bad weather, and by mechanical or chemical treatments such
as blow-drying, combing, bleaching, permanent-waving
and/or dyeing. As a result, the hair is often difficult to
manage, for instance it becomes difficult to disentangle or
style. A head of hair, even of lush hair, has difficulty in
maintaining an attractive style due to the fact that the hair
can lack vigor, volume and liveliness.
[0004] Thus, in order to overcome this, it is common
practice to use styling products that allow the hair to be
conditioned, for example, by giving it body, mass or volume.
[0005] These styling products are generally cosmetic hair
compositions comprising at least one polymer with high
affinity for the hair, which usually have the function of
forming a film on the hair surface in order to modify its
surface properties, such as to condition it.
[0006] One drawback associated with the use of these hair
compositions lies in the fact that the cosmetic effects
imparted by such compositions have a tendency to disap-
pear, for instance, after the first shampoo wash.
[0007] In order to overcome this drawback, it may be
envisaged to increase the remanence of the deposit of
polymers by directly performing free-radical polymerization
of certain monomers on the hair. However, the treatments
used thus far tend to result in the degradation of the fiber and
the hair treated in such a manner is generally difficult to
disentangle.
[0008] Moreover, it is known practice, for example from
French Patent No. FR 2 833 489, to use anionic-polymer-
izing electrophilic monomers directly at the surface of the
hair in the presence of a nucleophilic agent such as hydrox-
ide ions (OH‘) contained in water at neutral pH. Thus, once
applied to the hair, these monomers form a polymer that
leads to a coating. However, the coating obtained using these
compositions does not show satisfactory resistance relative
to the various attacking factors to which the hair may be
subjected.
[0009] There is thus a real need to find cosmetic compo-
sitions, for instance to condition the hair, that are remanent
to shampooing and to external attack, while at the same time
Feb. 14, 2008
maintain good cosmetic properties, such as providing long-
lasting body, mass or volume to the hair.
[0010] Thus, one aspect of the present disclosure is a
cosmetic composition for treating keratin fibers, for instance
human keratin fibers such as the hair, comprising:
[0011] at least one liquid organic solvent,
[0012]
[0013] at least one organofluorine compound compris-
ing at least 4 carbon atoms, with the exception of
polytetrafluoroethylene, and pigments coated with
fluoro compounds.
at least one electrophilic monomer, and
[0014] By applying such a composition, remanent coating
can be obtained, which can have, for example, good resis-
tance to shampooing and to external attack such as that
caused by perspiration, light and fatty substances such as
sebum. Moreover, the composition as disclosed herein
affords a long-lasting improvement in the body, mass and
volume of the hair.
[0015] The coating can be in the form of a smooth,
uniform deposit that shows excellent adhesion to the hair.
[0016] As disclosed herein, the at least one electrophilic
monomer, the at least one liquid organic solvent and the at
least one fluoro compound are different compounds.
[0017] Another aspect of the present disclosure relates to
a cosmetic process for treating keratin fibers using the
cosmetic composition as disclosed herein.
[0018] The present disclosure also relates to the use of the
cosmetic composition for treating keratin fibers.
[0019] A further aspect of the present disclosure is a
multi-compartment device or kit comprising, in at least one
first compartment, a composition (C) comprising at least one
electrophilic monomer and, in at least one second compart-
ment, a composition (D) comprising at least one organof-
luorine compound comprising at least 4 carbon atoms, with
the exception of polytetrafluoroethylene, and pigments
coated with fluoro compounds, wherein one and/ or the other
of composition (C) and composition (D) further comprising
at least one liquid organic solvent.
[0020] Other subjects, characteristics, aspects and benefits
of the present disclosure will emerge even more clearly upon
reading the description and the examples that follow.
[0021] The at least one electrophilic monomer present in
the composition of the present disclosure can be chosen
from:
[0022] the benzylidene malononitrile derivatives (A),
2-(4-chloro-benzylidene)malononitrile (Al), ethyl 2-cy-
ano-3-phenylacrylate (B), and ethyl 2-cyano-3-(4-chlo-
rophenyl)acrylate (Bl) described in Sayyah, J. Polymer
Research, 2000, p. 97:
(A)
CO2Et
Ph \2\CN
US 2008/0038218 A1
-continued
(A1)
CO2Et
/
CN
(B)
CN
Ph \2\CN
C1
(B1)
CN
/
CN
[0023] methylidenemalonate derivatives, for instance:
[0024] diethyl 2-methylenemalonate (C) by Hoplf, Mak-
romoleculare Chemie [Macromolecular Chemistry],
1961, p. 95, De Keyser, J Pharm. Sci, 1991, p. 67 and
Klemarczyk, Polymer, 1998, p. 173:
(C)
CO2Et
2\CO2Et
[0025] ethyl 2-ethoxycarbonylmethylenecarbonylacrylate
(D) by Breton, Biomazerials, 1998, p. 271 and Couvreur,
Pharmaceutical Research, 1994, p. 1270:
(D)
OEt
OEt
[0026] itaconate and itaconimide derivatives, for instance:
[0027] dimethyl itaconate (E) by Bachrach, European
Polymer Journal, 1976, p. 563:
(E)
CO2Me
)\/CO2Me
[0028] N-butyl itaconimide (F), N-(4-tolyl) itaconimide
(G), N-(2-ethylphenyl) itaconimide (H), N-(2,6-dieth-
ylphenyl) itaconimide (I) by Wanatabe, J. Polymer Sci-
ence: ParZA.' Polymer chemistry, 1994, p. 2073:
Feb. 14, 2008
[0029] R=Bu (F), 4-tolyl (G), 2-ethylphenyl (H), 2,6-
diethylphenyl (I)
[0030] the derivatives methyl ot-(methylsulfonyl)acrylate
(K), ethyl ot-(methylsulfonyl)-acrylate (L), methyl
ot-(tert-butylsulfonyl)acrylate (M), tert-butyl ot-(methyl-
sulfonyl)acrylate (N) and tert-butyl 0t-(tert-butylsulfony-
l)acrylate (O), by Gipstein, J. Org. Chem, 1980, p. 1486
and
[0031] the derivatives 1,1-bis(methylsulfonyl)ethylene
(P), 1-acetyl-1-methylsulfonylethylene (Q), methyl ot-(me-
thylsulfonyl)vinylsulfonate (R) and a-methylsulfonylacry-
lonitrile (S), as described in U. S. Pat. No. 2,748,050:
(K)
SO2Me
)
CO2Me
(L)
SO2Me
)
CO2Et
(M)
SO2t—Bu
)
CO2Me
(N)
SO2Me
)
CO2t—Bu
(0)
SO2t—Bu
)
CO2t—Bu
(P)
SO2Me
)
SO2Me
(Q)
SO2Me
)
COMe
(R)
SO2Me
)
SO3Me
(S)
CN
)
SO2Me
US 2008/0038218 A1
[0032] the methyl vinyl sulfone (T) and phenyl vinyl
sulfone (U) derivatives by Boor, J. Polymer Science,
1971, p. 249:
(T)
/\so2Me
(U)
/\so2Ph
[0033] the phenyl vinyl sulfoxide derivative (V) by
Kanga, Polymer preprints (ACS, Division of Polymer
Chemistry), 1987, p. 322:
(V)
/\s“ Ph
|
O.
[0034] the derivative 3 -methyl-N-(phenylsulfonyl)-1-aza-
1,3-butadiene (W) by Bonner, Polymer Bulletin, 1992, p.
517:
Y§NSO2Ph
[0035]
(W)
acrylate and acrylamide derivatives, for instance:
[0036] N-propyl-N-(3-triisopropoxysilylpropyl)acry-
lamide O() and N-propyl-N-(3-triethoxysilylpropyl)acry-
lamide (Y) by Kobayashi, Journal of Polymer Science,
PartA.' Polymer Chemistry, 2005, p. 2754:
_ (X)
l|’r (|)1Pr
N S"
/ ]\OiPr
OiPr
O
(Y)
l|’r (|)Et
N S"
/ ]\OEt
OEt
O
[0037] 2-hydroxyethyl acrylate (Z) and 2-hydroxyethyl
methacrylate (AA) by Rozenberg, International Journal
ofPlastics Technology, 2003, p. 17:
/YO\K\OH
0
(Z)
Feb. 14, 2008
-continued
(AA)
O\/\OH
[0038] N-butyl acrylate (AB) described in Schmitt, Mac-
romolecules, 2001, p. 2115, and
[0039] tert-butyl acrylate (AC) described in lshizone,
Macromolecules, 1999, p. 955:
OBu (AB)
/Y
O
OtBu (AC)
/Y
O
[0040] The electron-withdrawing monomer that is useful
in the present disclosure may be cyclic or linear. When it is
cyclic, the electron-withdrawing group can be exocyclic, for
example. In other words, it does not form an integral part of
the cyclic structure of the monomer.
[0041] According to at least one embodiment, these mono-
mers may comprise at least two electron-withdrawing
groups.
[0042] By way of non-limiting example, the monomers
comprising at least two electron-withdrawing groups, may
be made of the monomers of formula (I):
(1)
R1 R3
R2 R4
[0043] wherein:
[0044] R1 and R2 are, independently of each other, chosen
from sparingly and non-electron-withdrawing groups (spar-
ingly or non-inductive-withdrawing) such as:
[0045]
[0046] a saturated or unsaturated, linear, branched or
cyclic hydrocarbon-based group, for example contain-
ing from 1 to 20 carbon atoms, and further still from 1
to 10 carbon atoms, and optionally comprising at least
one entity chosen from nitrogen, oxygen or sulfur, and
optionally substituted with at least one group chosen
from AR, %OOR, %OR, —SH, —SR and
—OH, and halogens,
[0047] a modified or unmodified polyorganosiloxane
residue,
[0048]
a hydrogen atom,
a polyoxyalkylene group,
US 2008/0038218 A1
[0049] R3 and R4 are, independently of each other, an
electron-withdrawing (or inductive-withdrawing) group
that, according to at least one embodiment, may be chosen
from —N(R)3*, S(R)2*, SH2", NH3*, N02,
—SO2R, —CaN, —COOH, —COOR, %OSR,
—CONH2, %ONHR, —F, £1, —Br, —I, —OR,
—COR, —SH, —SR and —OH groups, linear and branched
alkenyl groups, linear and branched alkynyl groups, C1-C4
mono- or polyfluoroalkyl groups, aryl groups such as phe-
nyl, and aryloxy groups such as phenoxyloxy,
[0050] R is chosen from saturated and unsaturated, linear,
branched and cyclic hydrocarbon-based groups, for instance
containing from 1 to 20 carbon atoms and further, for
example, from 1 to 10 carbon atoms, and optionally com-
prising at least one entity chosen from nitrogen, oxygen and
sulfur, and optionally substituted with at least one entity
chosen from —OR', —COOR', —COR', —SH, —SR',
—OH, halogens, and polymer residues, this polymer possi-
bly being obtained by free-radical polymerization, by poly-
condensation or by ring opening, where R‘ is a C1-C10 alkyl
group.
[0051] As used herein, the term “electron-withdrawing or
inductive-withdrawing group (—I)’’ means any group that is
more electronegative than carbon. For instance, reference
may be made to the publication P. R. Wells, Prog. Phys. Org.
Chem., Vol. 6, p. 111 (1968).
[0052] As used herein, the term “sparingly or non-elec-
tron-withdrawing group” mean any group whose electrone-
gativity is less than or equal to that of carbon.
[0053] The alkenyl or alkynyl groups may contain from 2
to 20 carbon atoms and further still, for example, from 2 to
10 carbon atoms.
[0054] As saturated or unsaturated, linear, branched or
cyclic hydrocarbon-based groups may contain from 1 to 20
carbon atoms, for example, non-limiting mention may be
made of linear or branched alkyl, alkenyl or alkynyl groups,
such as methyl, ethyl, n-butyl, tert-butyl, isobutyl, pentyl,
hexyl, octyl, butenyl or butynyl; cycloalkyl or aromatic
groups.
[0055] Examples of substituted hydrocarbon-based groups
that may be mentioned include but are not limited to
hydroxyalkyl and polyhaloalkyl groups.
[0056] Examples of unmodified polyorganosiloxanes that
may be mentioned include but are not limited to polyalkyl-
siloxanes such as polydimethylsiloxanes, polyarylsiloxanes
such as polyphenylsiloxanes, and polyarylalkylsiloxanes
such as polymethylphenylsiloxanes.
[0057] By way of example, the modified polyorganosilox-
anes that may be mentioned include but are not limited to
polydimethylsiloxanes containing polyoxyalkylene and/or
siloxy and/or silanol and/or amine and/or imine and/or
fluoroalkyl groups.
[0058] The polyoxyalkylene groups that may be men-
tioned include but are not limited to polyoxyethylene groups
and polyoxypropylene groups, for instance those containing
1 to 200 oxyalkylene units.
[0059] Among the mono- or polyfluoroalkyl groups that
may be mentioned include but are not limited to groups such
Feb. 14, 2008
as (CH2)n (CF2)m CF3 or
with n=l to 20 and m=l to 20.
(CH2)n
(CF2)m CHF2
[0060] The substituents Rl to R4 may optionally be sub-
stituted with a group having cosmetic activity. The groups
with cosmetic activities that may be used include those
obtained from groups having coloring, antioxidant, UV-
screening and conditioning functions.
[0061] As examples of groups having a coloring function,
non-limiting mention may be made of azo, quinone,
methine, cyanomethine and triarylmethane groups.
[0062] As examples of groups having an antioxidant func-
tion, non-limiting mention may be made, for instance, of
groups of butylhydroxyanisole (BHA), butylhydroxytoluene
(BHT) or vitamin E type.
[0063] As examples of groups having a UV-screening
function, non-limiting mention may be made, for instance,
of groups of the benzophenone, cinnarnate, benzoate, ben-
zylidenecamphor and dibenzoylmethane type.
[0064] As examples of groups having a conditioning func-
tion, non-limiting mention may be made, for example of
cationic groups and groups of fatty ester type.
[0065] Among the at least one electrophilic monomers
mentioned above, according to at least one embodiment, the
monomers of the cyanoacrylate family and the derivatives
thereof of formula (II) may be used:
(11)
R1 CN
R2 COXR’3
[0066] wherein:
[0067] X is chosen from NH, S and O,
[0068] R1 and R2 are defined as above, and according to
at least one embodiment, R1 and R2 are hydrogen atoms,
[0069] R'3 is chosen from a hydrogen atom or R, as
defined in formula (I).
[0070] According to another embodiment, X is O.
[0071] Compounds of formula (II) that may be mentioned
include, but are not limited to the monomers:
[0072] a) belonging to the family of polyfluoroalkyl 2-cy-
anoacrylates such as the ester 2,2,3,3-tetrafluoropropyl 2-cy-
ano-2-propenoate of formula (III):
(111)
H COO—CH2—CF2—CHF2
US 2008/0038218 A1
[0073] or the ester 2,2,2-trifluoroethyl 2-cyano-2-prope-
noate of formula (IV):
(IV)
H COO—CH2—CF3
[0074] b) the alkyl or alkoxyalkyl 2-cyanoacrylates of
formula (V):
(V)
R1 CN
R2 COOR3
[0075] wherein:
[0076] R1 and R2 are defined as above,
[0077] R'3 is a C1-C10, (C1-C4)alkoxy(C1-C1O)alkyl or
C2-C10 alkenyl radical.
[0078] For example, non-limiting mention may be made
of ethyl 2-cyanoacrylate, methyl 2-cyanoacrylate, n-propyl
2-cyanoacrylate, isopropyl 2-cyanoacrylate, tert-butyl 2-cy-
anoacrylate, n-butyl 2-cyanoacrylate, isobutyl 2-cyanoacry-
late, 3-methoxybutyl cyanoacrylate, n-decyl cyanoacrylate,
hexyl 2-cyanoacrylate, 2-ethoxyethyl 2-cyanoacrylate,
2-methoxyethyl 2-cyanoacrylate, 2-octyl 2-cyanoacrylate,
2-propoxyethyl 2-cyanoacrylate, n-octyl 2-cyanoacrylate,
allyl 2-cyanoacrylate, methoxypropyl 2-cyanoacrylate and
isoamyl cyanoacrylate.
[0079] In the context of the present disclosure, the mono-
mers defined in b) may be used. For example, according to
one embodiment, the at least one electrophilic monomer is
a cyanoacrylate monomer chosen from C6-C10 alkyl
cyanoacrylates.
[0080] The monomers that may be used include but are not
limited to the octyl cyanoacrylates of formula (VI) and
mixtures thereof:
(V1)
H CN
H COOR3
[0081] wherein R'3 is chosen from the following radicals:
[0082] —(CH2)7%H3;
[0083] —CH(CH3)—(CH2)5%H3;
[0084] —CH2—CH(C2H5)—(CH2)3%H3;
[0085] —(CH2)5%H(CH3)%H3; and
[0086] —(CH2)4%H(C2H5)%H3.
[0087] The monomers used in accordance with the present
disclosure may be covalently bonded to at least one support
Feb. 14, 2008
chosen from polymers, oligomers and dendrimers. The
polymer or the oligomer may be linear, branched, in comb
form or in block form. The distribution of the monomers of
the present disclosure over the polymeric, oligomeric or
dendritic structure may be random, in an end position or in
the form of blocks.
[0088] According to at least one embodiment, the at least
one electrophilic monomer is present in an amount ranging
from 0.2% to 50% by weight, for example in an amount
ranging from 0.5% to 30% by weight relative to the total
weight of the cosmetic composition.
[0089] In the context of the present disclosure, the at least
one electrophilic monomer of formula (I) may include
monomers capable of undergoing anionic polymerization in
the presence of at least one nucleophilic agent.
[0090] As used herein, the term “anionic polymerization”
means the mechanism defined in the book “Advanced
Organic Chemistry,” Third Edition by Jerry March, pages
151 to 161.
[0091] The nucleophilic agents capable of initiating the
anionic polymerization are systems that are known per se,
which are capable of generating a carbanion on contact with
a nucleophilic agent, such as the hydroxide ions contained in
water at neutral pH. The term “carbanion” refers to the
chemical species defined in “Advanced Organic Chemistry,”
Third Edition, by Jerry March, page 141.
[0092] The nucleophilic agents may be applied indepen-
dent of the composition of the present disclosure. They may
also be added to the composition at the time of use.
[0093] The at least one nucleophilic agent is a molecular
compound, an oligomer, a dendrimer or a polymer contain-
ing nucleophilic functional groups. In a non-limiting man-
ner, nucleophilic functional groups that may be mentioned
include the following groups: R2N‘, NH2‘, Ph3C’, R3C‘,
PhNH‘, pyridine, ArS‘, R—CaC', RS", SH‘, R0‘, RZNH,
ArO‘, N3‘, OH‘, ArNH2, NH3, I‘, Br‘, Cl‘, RCOO‘, SCN‘,
ROH, RSH, NCO‘, CN‘, N03‘, C104‘ and H20, where Ph
is a phenyl group; Ar is an aryl group, and R is a C1-C10 alkyl
group.
[0094] The at least one electrophilic monomer of formula
(I) as disclosed herein may be synthesized according to the
known methods described in the art. For instance, the
cyanoacrylate monomers may be synthesized according to
the teaching ofU.S. Pat. Nos. 3,527,224; 3,591,767; 3,667,
472; 3,995,641; 4,035,334; and 4,650,826.
[0095] For the purposes of the present disclosure, the term
“fluoro compound” means any organic compound compris-
ing at least one fluorine atom, and comprising at least 4
carbon atoms. For instance, perfluoro compounds may be
used, i.e. compounds for which the hydrogen atoms associ-
ated with at least one carbon atom are totally replaced with
fluorine atoms.
[0096] This fluoro compound may be in the form of a
defined compound or of a polymer, a silicone or a copoly-
mer.
US 2008/0038218 A1
[0097] Such compounds are described, for example, in
Ullmann’s Industrial Chemistry Encyclopedia in the chap-
ters on fluoro polymers (fluoroplastics and fluoroelastomers)
and organic fluorine compounds.
[0098] According to at least one embodiment, the fluoro
compound is not an acrylate-based grafted silicone polymer.
[0099] According to at least one embodiment, when the
fluoro compound is liquid at 25° C. and atmospheric pres-
sure, then the at least one liquid organic solvent is not
fluorinated.
[0100] Among the fluoro compounds as defined herein,
non-limiting mention may be made of:
[0101] i) fluorosilicone compounds of formula (V11):
(V11)
R1 R1 CH3 R1
R2—Si?O ;i?O 5i?O 5i?R2
1. 1. 1 1 1
11
[0102] wherein:
[0103] R is chosen fro1n C1-C6 linear and branched
divalent alkyl groups such as divalent methyl, ethyl,
propyl and butyl groups,
[0104] Rf is chosen from C1-C12fluoroalkyl radicals,
such as a perfluoroalkyl radical, for example a C1-C9
fluoroalkyl radical,
[0105] R1 is chosen from, independently of each other,
C1-C20 alkyl radicals, hydroxyl radicals, and phenyl
radicals,
[0106] R2 is R1 or Rf,
[0107] m is chosen from 0 to 500, for example from 0
to 200, and
[0108] n is chosen from 1 to 1000, for example from 1
to 500.
[0109] According to at least one embodiment, the groups
R1 are identical and are methyl radicals.
[0110] Such compounds include those sold by the com-
pany Shin-Etsu under the names FL-5, FL-10, X22-821 and
X22-822 or FL-100 by the company Dow Coming, under
the name FS-1265 Fluid by the company Phoenix Chemical,
under the name Pecosil FS or under the names Pecosil
FSL-150, Pecosil FSL-300, Pecosil FSH-150, Pecosil FSH-
300, Pecosil FSU-150 and Pecosil FSU-300.
[0111] ii) perfluorocycloalkyl compounds
[0112] For example, non-limiting mention may be made of
the perfluorocycloalkyls chosen from those of formula
(V111):
Feb. 14, 2008
(VIII)
/\
(CF2)n [CF — (CF2)p — Flm
[0113] wherein n is equal to 3, 4 or 5, m is equal to 1 or
2, and p is equal to 0,1, 2 or 3; with the proviso that when
m=2, the groups are not necessarily alpha to each other. The
compounds of formula (V 111) that may be mentioned include
but are not limited to perfluoromethylcyclopentane and
1,3-perfluorodimethylcyclohexane, sold, respectively, under
the names Flutec PC1® and Flutec PC3® by the company
F2 Chemicals, and also perfluorodimethylcyclobutane.
[0114] The perfluorocycloalkyl compounds that may also
be mentioned include but are not limited to polycyclic
compounds. For example, non-limiting mention may be
made of perfluorodecalin and perfluoroperhydrophenan-
threne, which are sold, respectively, under the names Flutec
PC6® and Flutec PC11® by the company F2 Chemicals.
[0115] iii) the fluoroalkyl or heterofluoroalkyl compounds
chosen from those of formula (IX):
CH3*(CH2)r.%Z].-X41‘; (IX)
[0116] wherein:
[0117] t is 0 or 1;
[0118] n is 0,1,2 or 3;
[0119] X is chosen from linear and branched divalent
perfluoroalkyl radicals containing from 2 to 5 carbon atoms;
and
[0120] Z is chosen from O, S and NR; wherein
[0121] R is chosen from hydrogen, —(CH2 n—CH3 and
—(CF2)m—CF3 radicals; and
[0122] m is 2, 3, 4 or 5.
[0123] Among the fluoroalkyl or heterofluoroalkyl com-
pounds of formula (IX) that may be mentioned, by way of
non-limiting example, are methoxynonafluorobutane sold
under the name MSX 4518®, HFE-00® by the company 3M
and ethoxynonafluorobutane sold under the name HFE-
7200® by the company 3M.
[0124] iv) the perfluoroalkane compounds chosen from
those of formula Oi):
CF3T(CF2)n4CF3
[0125] wherein n ranges from 2 to 16, for example from 2
to 6.
[0126] The perfluoroalkane compounds of formula (X)
that may be mentioned include but are not limited to
perfluoro hexane, dodecafluoropentane and tetradecafluoro-
hexane.
[0127] v) the perfluoropolyethers chosen from those of
formulae (XI) and Gill):
(X1)
CF3
F—[—c1=—c1=2—o—];c1=2—c1=3
US 2008/0038218 A1
[0128] wherein n ranges from 7 to 30; and
(X11)
CF3
CF3—[-O—CF—CF2-]m—[-O—CF2-]p—OCF3
[0129] wherein the ratio m/p ranges from 20 to 40, and the
molecular weight ranges from 500 to 20,000.
[0130] Among these perfluoropolyethers of formulae Oil)
and (X11), non-limiting mention may be made, respectively,
of the product sold under the name Fluortress LM36® by the
company DuPont, and those sold under the general name
Fomblin by the company Montefluos, for example Fomblin
HC R®.
[0131] It is also possible to use the perfluoropolyethers
mentioned in European Patent Application No. EP-A-641
194, the content of which is incorporated into the present
disclosure by way of reference.
[0132] vi) the perfluoromorpholine derivatives chosen
from those of formula (X111):
(X111)
R
)\
FZC CF2
FZC CF;
\O/
[0133] wherein R is a C1-C4 perfluoroalkyl radical.
[0134] The perfluoromorpholine derivatives of formula
(XIII) that may be mentioned include but are not limited to
4-trifluoromethylperfluoromorpholine and 4-pentafluoroet-
hylperfluoromorpholine.
[0135] vii) the fluoro esters chosen from those of formula
(XIV):
(XIV)
CF3—(CF2)c—(CH2)d—0—|C—A—f—0—(CH2)d—(CF2)c—CF3
OR4O
[0136] wherein:
[0137] R4 is chosen from a hydrogen atom and a radical
:C—0—(CH2)d—(CF2)c—CF3,
O
[0138] A is a linear or branched, optionally hydroxylated,
C1-C18 alkylene or alkenylene chain,
[0139]
[0140] d ranges from 1 to 18.
c ranges from 1 to 17, and
Feb. 14, 2008
[0141] The compounds of formula OHV) that may be
mentioned include but are not limited to 2F-octylethyl-1,
12-dodecanedioate of the following formula:
C8F17‘C2H5—O—C:(CH2)10-C—0’C2H5—C8F17
ll
0 0
and C1-C6 perfluoroalkyl tricitrates, such as the perfluorobu-
tyl tricitrate sold under the name Zonyl TBC® by the
company DuPont.
[0142] viii) perfluoroalkylpolyacrylate-based copolymers.
[0143] For instance, according to at least one embodiment,
the portion of the copolymer containing the perfluoroalky-
lpolyacrylate is formed by the polymerization of a monomer
of acrylic type or of acrylamide type, such as those having
the formula (A'):
(A')
H2c—|—"—X—(Y)z—R,
R40
[0144] wherein:
[0145] R4 is chosen from hydrogen and C1-C4 alkyl
radicals,
[0146] X is chosen from O and —N—R2, for which R2
is chosen from hydrogen and C1-C10 alkyl and
hydroxyalkyl radicals,
[0147] Y is chosen from C1-C6 alkylene radicals,
[0148]
[0149] R5 is chosen from linear and branched C1-C20
alkyl radicals, all or some of the hydrogen atoms of
which are replaced with fluorine atoms or a radical
containing perfluoropolyether groups.
z is equal to 0 or 1,
[0150] By way of example, the fluoro monomer may be
chosen from those of formula:
CH2=CH—C—0—(C2H4)x— (CF2)n—CF3
O
[0151] wherein:
[0152] n ranges from 4 to 16, where according to at least
one embodiment, n is equal to 5, 7, 9 or 11; and
[0153] x is equal to 1 or 2.
[0154] The fluoro monomer may also be chosen from
those of formula:
CH2=C—C—0— (C2H4)x—(CF2)m—CF3
||
CH3 0
US 2008/0038218 A1
[0155] wherein:
[0156] m ranges from 4 to 16, where according to at least
one embodiment, m is equal to 5, 7, 9 or 11; and
[0157] x is equal to 1 or 2.
[0158] The non-fluoro portion of the copolymer may be
derived from monomers of the type B‘ or C‘ used alone or in
combination, for example:
Monomer B‘:
[0159] Alkyl (meth)acrylate-based monomer chosen from
those of formula (B‘):
(3')
CH2:C:C:O*R2
ll
R1 0
[0160] wherein:
[0161] R1 is chosen from a hydrogen atom and C1-C4
alkyl radicals and
[0162] R2 is chosen from C1-C20, such as C2-C8, alkyl
radicals, C2-C6, such as C2-C4 hydroxycarbon radicals,
and radicals —(CH2)6,N11,R3 where R3 is chosen
from C1-C6 alkyl and cycloalkyl groups, and n is an
integer that ranges from 1 to 4.
[0163] According to at least one embodiment, the radical
R1 of the monomer of formula B‘ is chosen from hydrogen
and methyl, ethyl, n-butyl and isopropyl radicals.
[0164] The monomers of formula B‘ may be chosen from
acrylic acid, methacrylic acid, methyl (meth)acrylate, ethyl
(meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acry-
late, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate,
hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth-
)acrylate, and mixtures thereof, for example.
[0165] As disclosed herein, the fluoro copolymers of the
present disclosure may be manufactured as described in
French Patent Nos. FR-A-2 175 332 and FR-A-2 540 131
and European Patent No. EP-A-206 671.
[0166] These copolymers are, for example, those sold by
Cognis under the brand name Repellan, those sold by
Mitsubishi Chemicals under the brand name Repearl, or
those sold by Clariant under the brand name Cartafluor UH
Liquid.
Monomer C‘:
[0167] Monomer comprises an alkyl(meth)acrylamide
unit chosen from those of formula C‘:
(C')
H2C=l_H—T_“
R1 0 R3
Feb. 14, 2008
[0168] wherein R1 is H or CH3;
[0169] R2 and R3, which may be identical or different, are
chosen from H, linear and branched, saturated and unsatur-
ated C1-C40 hydrocarbon-based radicals, optionally substi-
tuted with at least one group chosen from hydroxyl, car-
boxylic acid, sulfonic acid and phosphonic acid groups,
which may or may not be esterified, C5-C10 cycloalkyl and
C5-C10 aryl groups, optionally substituted with at least one
group chosen from linear and branched C1-C4 alkyl,
hydroxyl, carboxylic acid and sulfonic acid groups or pos-
sibly comprising, at its ends or within the group, at least one
heteroatom chosen from O, S, N, Si and P, or a carbonyl
group, or optionally comprising at least one heteroatom
chosen from O, S and N.
[0170] By way of example, the (meth)acrylamide units
that may be mentioned include but are not limited to
N-tert-butylacrylamide, N-tert-hexylacrylamide, N-tert-oc-
tylacrylamide, N-octylacrylarnide, N-decylacrylamide,
N-dodecylacrylarnide and N-methylundecylacrylamide.
[0171] ix) fluoro compound containing the following sub-
unit:
R1
—(cH2—c)—
[0172] wherein:
[0173] R1 is chosen from a hydrogen atom and C1-C4
alkyl radicals;
[0174] R2 is chosen from a hydrogen atom and C1-C10
alkyl or hydroxyalkyl radicals;
[0175] Y and Y‘ are C1-C6 alkylene radicals; and
[0176] Rf is chosen from linear and branched C1-C20
alkyl radicals, all or some of the hydrogen atoms of
which are replaced with fluorine atoms or a radical
containing perfluoropolyether groups.
[0177] For instance, the fluoro copolymers of the present
disclosure may be synthesized as described in documents
FR-A-2 175 332 and FR-A-2 540 131.
[0178] Examples of these copolymers may be found in the
Scotchgard range sold by 3M, the formula of which is as
follows:
US 2008/0038218 A1
R1 CH3 cfi
0
Feb. 14, 2008
CH3 R1
H—[—c—cH2-17s—[—cH2—cH—c—o—(cH2—cH2—o)4—c—cH—cH2—s-]T[—cH2—c-17H
O
C2H4
N(R2)
so;
C2H4
CSFI7
or in the Foraperle range sold by the company Atochem, the
structure of which is as follows:
0
H—(o—cH2—cH2),,—o—c—cH2—s—(cH2—cH),,,—H
o
O
C2H4
I|\I(CH3)
so;
C2H4
I
CsF13
[0179] x) The fluoro compound may also be a copolymer
based on fluoroethylene-alkyl vinyl ether. As a compound
belonging to this family, non-limiting mention may be made
of, for example, the Lumiflon range sold by Asahi Glass.
[0180] xi) The fluorohydrocarbons mentioned in Patent
Application EP-A-609 132, the content of which is incor-
porated into the present disclosure by way of reference, may
also be used as fluoro oils.
[0181] As a compound belonging to this family, non-
limiting mention may be made of 1-(2'-fluorohexyleth-
ylthio)-3-(2"-ethylhexyloxy)-2-propanol.
[0182] By way of example, the fluoro compounds may be
chosen from fluorosilicone compounds, perfluorocy-
cloalkyls, perfluoropolyethers and perfluoroalkylpolyacry-
late-based copolymers.
[0183] These fluoro compounds may be soluble or in
dispersion in the medium of the composition. They may also
be in the form of particles in dispersion, the dispersion
optionally comprising at least one alcohol and/or ketone in
low amount, this dispersion possibly being diluted in any
proportion with water.
[0184] As disclosed herein, the fluoro compounds are
present in the cosmetic composition in an amount generally
ranging from 0.1% to 20% by weight, such as in an amount
0
C2H4
N(R2)
so;
C2H4
CSFI7
ranging from 0.2% to 15% by weight and further, for
example, in an amount ranging from 0.5% to 10% by weight
relative to the total weight of the said cosmetic composition.
[0185] As used herein, the term “organic solvent” means
an organic substance capable of dissolving another sub-
stance without chemically modifying it.
[0186] The at least one liquid organic solvent that may
prove useful in the cosmetic composition according to the
present disclosure can be chosen from compounds that are
liquid at a temperature of 25° C. and at 105 Pa (760 mmHg).
[0187] The at least one liquid organic solvent can be
chosen, for example, from: aromatic alcohols such as benzyl
alcohol; liquid fatty alcohols, for example C10-C30 aromatic
alcohols; modified or unmodified polyols such as glycerol,
glycol, propylene glycol, dipropylene glycol, butylene gly-
col or butyl diglycol; volatile silicones such as cyclopenta-
siloxane or cyclohexasiloxane; polydimethylsiloxanes
optionally modified with alkyl and/or amine and/or imine
and/or fluoroalkyl and/or carboxylic and/or betaine and/or
quatemary ammonium functional groups, modified liquid
polydimethylsiloxanes, mineral, organic and/or plant oils,
alkanes, such as C5-C10 alkanes; and liquid fatty acids,
liquid fatty esters and further for example, liquid fatty
alcohol benzoates and salicylates.
[0188] The organic solvent may also be chosen from
organic oils; silicones such as volatile silicones, amino or
non-amino silicone gums or oils and mixtures thereof;
mineral oils; plant oils such as olive oil, castor oil, rapeseed
oil, coconut oil, wheatgerm oil, sweet almond oil, avocado
oil, macadamia oil, apricot oil, safflower oil, candlenut oil,
camelina oil, tamanu oil or lemon oil, or alternatively
organic compounds such as C5-C10 alkanes, acetone, methyl
ethyl ketone, esters of liquid C1-C20 acids and of C1-C8
alcohols such as methyl acetate, butyl acetate, ethyl acetate
and isopropyl myristate, dimethoxyethane, diethoxyethane,
liquid C10-C30 fatty alcohols such as oleyl alcohol, esters of
liquid C10-C30 fatty alcohols such as C10-C30 fatty alcohol
benzoates, and mixtures thereof; polybutene oil, isononyl
isononanoate, isostearyl malate, pentaerythrityl tetraisos-
tearate, tridecyl trimellitate, and the mixture of cyclopenta-
siloxane (14.7% by weight)/polydimethylsiloxane dihy-
droxylated in the (X and 00 positions (85.3% by weight), and
mixtures thereof. According to at least one embodiment, the
at least one liquid organic solvent is not fluorinated.
US 2008/0038218 A1
[0189] According to at least one embodiment, the at least
one liquid organic solvent comprises at least one silicone
such as liquid polydimethylsiloxanes and modified liquid
polydimethylsiloxanes, where their viscosity at 25° C.
ranges from 0.1 cSt to 1,000,000 cSt, for instance it ranges
from 1 cSt to 30,000 cSt.
[0190] Non-limiting mention may be made of the follow-
ing oils:
[0191] the mixture of 0t,u)-dihydroxylated polydimeth-
ylsiloxane/cyclopentadimethylsiloxane (1 4 .7/ 85 .3)
sold by Dow Corning under the name DC 1501 Fluid;
[0192] the mixture of 0t,u)-dihydroxylated polydimeth-
ylsiloxane/polydimethylsiloxane sold by Dow Corning
under the name DC 1503 Fluid;
[0193] the mixture of dimethicone/cyclopentadimethyl-
siloxane sold by Dow Coming under the name DC
1411 Fluid or the product sold by Bayer under the name
SF 1 21 4;
[0194] the cyclopentadimethylsiloxane sold by Dow
Coming under the name DC 245 Fluid;
[0195]
[0196] The composition of the present disclosure can
contain water. However, according to at least one embodi-
ment, the composition as disclosed herein is anhydrous, i.e.
it contains less than 1% by weight of water relative to the
total weight of the composition.
and the respective mixtures of these oils.
[0197] The at least one liquid organic solvent of the
composition is generally present in an amount ranging from
0.01% to 99%, for example from 50% to 99% by weight
relative to the total weight of the composition.
[0198] The cosmetic composition according to the present
disclosure may also comprise at least one pigment.
[0199] The use of at least one pigment in the cosmetic
composition in accordance with the present disclosure
makes it possible to obtain visible colorations even on dark
hair, without making it necessary to bleach the keratin fibers,
since the surface pigment masks the natural color of the
fiber.
[0200] The composition in accordance with the present
disclosure thus provides the benefit of producing colorations
that show good resistance to the various attacking factors to
which the hair may be subjected, such as fatty substances or
successive shampooing over time.
[0201] Thus, it is possible to obtain visible and very
chromatic colorations on a dark keratin fiber without it being
necessary to lighten or bleach the keratin fibers and, conse-
quently, without physical degradation of the keratin fibers.
[0202] For the purposes of the present disclosure, the term
“pigment” means any organic and/or mineral species whose
solubility in water is less than 0.01%, for instance less than
0.0001% at 20° C., having an absorption that ranges from
350 to 700 nm, for example at maximum absorption.
[0203] The at least one pigment that may be used can be
chosen from organic and/or mineral pigments known in the
art, for example those described in Kirk-Othmer’s Encyclo-
pedia of Chemical Technology and in Ullmann’s Encyclo-
paedia of Industrial Chemistry.
Feb. 14, 2008
[0204] These pigments may be in the form of powder or of
pigmentary paste. The pigments may be coated or uncoated.
[0205] As disclosed herein, the pigments may be chosen,
for example, from white or colored pigments, lakes, pig-
ments with special effects such as nacres or flakes, and
mixtures thereof.
[0206] Examples of white or colored mineral pigments
that may be mentioned in a non-limiting marmer include
titanium dioxide, which may or may not be surface-treated,
zirconium oxide or cerium oxide, iron oxide and chromium
oxide, manganese violet, ultramarine blue, chromium
hydrate and ferric blue. For example, the following mineral
pigments may be used: Ta2O5, Ti3O5, Ti2O3, TiO, ZrO2 as a
mixture with TiO2, ZrO2, Nb2O5, CeO2, ZnS.
[0207] Examples of white or colored organic pigments
that may be mentioned include but are not limited to nitro so,
nitro, azo, xanthene, quinoline, anthraquinone and phthalo-
cyanin compounds, compounds of metallic complex type,
and isoindolinone, isoindoline, quinacridone, perinone,
perylene, diketopyrrolopyrrole, thioindigo, dioxazine, triph-
enylmethane and quinophthalone compounds.
[0208] For example, the white or colored organic pig-
ments can be chosen from carmine, carbon black, aniline
black, azo yellow, quinacridone, phthalocyanin blue, sor-
ghum red, the blue pigments codified in the Color Index
under the references CI 42090, 69800, 69825, 73000, 74100,
74160, the yellow pigments codified in the Color Index
under the references CI 11680, 11710, 15985, 19140, 20040,
21100, 21108, 47000, 47005, the green pigments codified in
the Color Index under the references CI 61565, 61570,
74260, the orange pigments codified in the Color Index
under the references CI 11725, 15510, 45370, 71105, the red
pigments codified in the Color Index under the references CI
12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580,
15620, 15630, 15800, 15850, 15865, 15880, 17200, 26100,
45380, 45410, 58000, 73360, 73915, 75470, the pigments
obtained by oxidative polymerization of indole or phenolic
derivatives as described in French Patent No. 2 679 771.
[0209] Pigmentary pastes of organic pigment may be used,
such as the products sold by the company Hoechst under the
names:
[0210] Jaune Cosmenyl IOG: Pigment Yellow 3 (CI
11710);
[0211] Jaune Cosmenyl G: Pigment Yellow 1 (CI
11680);
[0212] Orange Cosmenyl GR: Pigment Orange 43 (CI
71105);
[0213] Rouge Cosmenyl R: Pigment Red 4 (CI 12085);
[0214] Carmin Cosmenyl FB: Pigment Red 5 (CI
12490);
[0215] Violet Cosmenyl RL: Pigment Violet 23 (CI
51319);
[0216] Bleu Cosmenyl A2R: Pigment Blue 15.1 (CI
74160);
[0217] Vert Cosmenyl GG: Pigment Green 7 (CI
74260); and
[0218] Noir Cosmenyl R: Pigment Black 7 (CI 77266).
US 2008/0038218 A1
[0219] The pigments in accordance with the present dis-
closure may also be in the form of composite pigments as
described in European Patent EP 1 184 426. These compos-
ite pigments may be composed of, for example, particles
comprising a mineral core, at least one binder for fixing the
organic pigments to the core, and at least one organic
pigment at least partially covering the core.
[0220] As disclosed herein, the term “lakes” means dyes
adsorbed onto insoluble particles, the assembly thus
obtained remaining insoluble during use. The mineral sub-
strates onto which the dyes are adsorbed are, for example,
alumina, silica, calcium sodium borosilicate or calcium
aluminium borosilicate, and aluminium. Among the organic
dyes that may be used, non-limiting mention is made of
cochineal carmine.
[0221] Examples of lakes that may be mentioned in a
non-limiting manner include the products known under the
following names: D & C Red 21 (Cl 45 380), D & C Orange
5 (Cl 45 370), D & C Red 27 (Cl 45 410), D & C Orange
10 (Cl 45 425), D & C Red 3 (C145 430), D & C Red 7 (Cl
15 850:1), D & C Red 4 (Cl 15 510), D & C Red 33 (Cl 17
200), D & C Yellow 5 (Cl 19 140), D & C Yellow 6 (Cl 15
985), D & C Green (Cl 61 570), D & C Yellow 1 0 (Cl 77
002), D & C Green 3 (Cl 42 053), and D & C Blue 1 (Cl 42
090).
[0222] As disclosed herein, the term “pigments with spe-
cial effects” means pigments that generally create a colored
appearance (characterized by a certain shade, a certain
vivacity and a certain level of luminance) that is non-
uniform and that changes as a function of the conditions of
observation (light, temperature, angles of observation, etc.).
They are consequently in contrast with white or colored
pigments, which afford a standard opaque, semi-transparent
or transparent uniform shade.
[0223] Examples of pigments with special effects that may
be mentioned include white nacreous pigments such as mica
coated with titanium or with bismuth oxychloride, colored
nacreous pigments such as mica coated with titanium and
with iron oxides, mica coated with titanium, such as with
ferric blue or with chromium oxide, mica coated with
titanium and with an organic pigment as defined above, and
also nacreous pigments based on bismuth oxychloride.
Nacreous pigments that may be mentioned include but are
not limited to the Cellini nacre sold by Engelhard (Mica-
TiO2-lake), the Prestige nacre sold by Eckart (Mica-TiO2),
the Prestige Bronze nacre sold by Eckart (Mica-Fe203) and
the Colorona nacre sold by Merck (Mica-TiO2-Fe203).
[0224] Non-limiting mention may also be made of pig-
ments with an interference effect not bound to a substrate,
for instance liquid crystals (Helicones HC from Wacker),
holographic interference flakes (Geometric Pigments or
Spectra f/x from Spectratek). The pigments with special
effects also comprise fluorescent pigments, whether they are
substances that are fluorescent in daylight or that produce
ultraviolet fluorescence, phosphorescent pigments, photo-
chromic pigments, thermochromic pigments and quantum
dots, for example those sold by the company Quantum Dots
Corporation.
[0225] Quantum dots are luminescent semiconductive
nanoparticles capable of emitting, under light excitation,
radiation with a wavelength in the range of 400 nm to 700
Feb. 14, 2008
nm. These nanoparticles are known in the literature. For
instance, they may be manufactured according to the pro-
cesses described, for example, in U.S. Pat. Nos. 6,225,198 or
5,990,479, in the publications cited therein, and also in the
following publications: Dabboussi B. O. et al “(CdSe)ZnS
core-shell quantum dots: synthesis and characterisation of a
size series of highly luminescent nanocristallites”Journal of
Physical Chemistry B, Vol. 101, 1997, pp. 9463-9475 and
Peng, Xiaogang et al, “Epitaxial Growth of highly Lumi-
nescent CdSe/CdS core/ shell nanocrystals with photostabil-
ity and electronic accessibility”Journal of the American
Chemical Society, Vol. 119, No. 30, pp. 7019-7029.
[0226] The variety of pigments that may be used in the
present disclosure makes it possible to obtain a rich palette
of colors, for instance the possibility to obtain optical effects
such as metallic or interference effects.
[0227] According to at least one embodiment, the pig-
ments are colored pigments. The term “colored pigments”
means pigments other than white pigments.
[0228] The size of the pigment used in the cosmetic
composition according to the present disclosure generally
ranges from 10 nm to 200 pm, for example from 20 nm to
80 um and even further for example from 30 nm to 50 pm.
[0229] The pigments used in the cosmetic composition as
disclosed herein may be surface-treated with an organic
agent.
[0230] Thus, the pigments that have been surface-treated
beforehand, which are useful in the context of the present
disclosure, can be pigments that have totally or partially
undergone a surface treatment of chemical, electronic, elec-
trochemical, mechanochemical or mechanical nature, with
an organic agent such as those described in Cosmetics and
Toiletries, February 1990, Vol. 105, pp. 53-64, before being
dispersed in the composition in accordance with the present
disclosure. These organic agents may be chosen, for
example, from amino acids; waxes, for example carnauba
wax and beeswax; fatty acids, fatty alcohols and derivatives
thereof, such as stearic acid, hydroxystearic acid, stearyl
alcohol, hydroxystearyl alcohol and lauric acid and deriva-
tives thereof; anionic surfactants; lecithins; sodium, potas-
sium, magnesium, iron, titanium, zinc or aluminium salts of
fatty acids, for example aluminium stearate or laurate; metal
alkoxides; polysaccharides, for example chitosan, cellulose
and derivatives thereof; polyethylene; (meth)acrylic poly-
mers, for example polymethyl methacrylates; polymers and
copolymers containing acrylate units; proteins; alkanola-
mines; silicone compounds, for example silicones, polydim-
ethylsiloxanes, alkoxysilanes, alkylsilanes and siloxysili-
cates; organofluorine compounds, for example
perfluoroalkyl ethers; and fluorosilicone compounds.
[0231] The surface-treated pigments that may prove useful
in the cosmetic composition according to the present dis-
closure may also have been treated with a mixture of these
compounds and/ or may have undergone several surface
treatments.
[0232] The surface-treated pigments that may prove useful
in the context of the present disclosure may be prepared
according to surface-treatment techniques that are well-
known to those skilled in the art, or may be commercially
available in the required form.
US 2008/0038218 A1
[0233] For example, the surface-treated pigments may be
coated with an orgamc layer.
[0234] The organic agent with which the pigments are
treated may be deposited on the pigments by evaporation of
solvent, chemical reaction between the molecules of the
surface agent or creation of a covalent bond between the
surface agent and the pigments, for example.
[0235] The surface treatment may thus be performed, for
example, by chemical reaction of a surface agent with the
surface of the pigments and creation of a covalent bond
between the surface agent and the pigments or the fillers. For
instance, this method is described in U.S. Pat. No. 4,578,
266.
[0236] According to at least one embodiment, an organic
agent covalently bonded to the pigments will be used.
[0237] The agent for the surface treatment may be present
in an amount ranging from 0.1% to 50% by weight, for
instance from 0.5% to 30% by weight and further, for
example from 1% to 10% by weight relative to the total
weight of the surface-treated pigments.
[0238] The surface treatments of the pigments may be
chosen from the following treatments, by way of non-
limiting example:
[0239] a PEG-silicone treatment, for instance the AQ
surface treatment sold by LCW;
[0240] a chitosan treatment, for instance the CTS sur-
face treatment sold by LCW;
[0241] a triethoxycaprylylsilane treatment, for instance
the AS surface treatment sold by LCW;
[0242] a methicone treatment, for instance the SI sur-
face treatment sold by LCW;
[0243] a dimethicone treatment, for instance the Covasil
3.05 surface treatment sold by LCW;
[0244] a dimethicone/trimethyl siloxysilicate treatment,
for instance the Covasil 4.05 surface treatment sold by
LCW;
[0245] a lauroyllysine treatment, for instance the LL
surface treatment sold by LCW;
[0246] a lauroyllysine dimethicone treatment, for
instance the LUST surface treatment sold by LCW;
[0247] a magnesium myristate treatment, for instance
the MM surface treatment sold by LCW;
[0248] an aluminium dimyristate treatment, for instance
the MI surface treatment sold by Miyoshi;
[0249] an isostearyl sebacate treatment, for instance the
HS surface treatment sold by Miyoshi;
[0250] a disodium stearoyl glutamate treatment, for
instance the NAI surface treatment sold by Miyoshi;
[0251] a dimethicone/disodium stearoyl glutamate
treatment, for instance the SA/NAI surface treatment
sold by Miyoshi;
[0252] an acrylate/dimethicone copolymer and perfluo-
roalkyl phosphate treatment, for instance the FSA treat-
ment sold by Daito;
Feb. 14, 2008
[0253] a lauroyllysine/aluminium tristearate treatment,
for instance the LL-AlSt surface treatment sold by
Daito;
[0254] an octyltriethylsilane treatment, for instance the
OTS surface treatment sold by Daito;
[0255] an octyltriethylsilane/perfluoroalkyl phosphate
treatment, for instance the FOTS surface treatment sold
by Daito;
[0256] an acrylate/dimethicone copolymer treatment,
for instance the ASC surface treatment sold by Daito;
[0257] an isopropyl titanium triisostearate treatment,
for instance the ITT surface treatment sold by Daito;
[0258] a microcrystalline cellulose and carboxymethyl-
cellulose treatment, for instance the AC surface treat-
ment sold by Daito;
[0259] a cellulose treatment, for instance the C2 surface
treatment sold by Daito; and
[0260] an acrylate copolymer treatment, for instance the
APD surface treatment sold by Daito.
[0261] The at least one pigment may be generally present
in the composition in total amounts generally ranging from
0.05% to 50% by weight, for example from 0.1% to 35% by
weight and even further from 0.5% to 20% by weight
relative to the total weight of the composition.
[0262] The composition in accordance with the present
disclosure may further comprise at least one pigment that
has not been surface-treated.
[0263] The medium of the composition of the present
disclosure may also be in the form of an emulsion and/or
may be encapsulated, the electrophilic monomers being
maintained in an anhydrous medium until the time of use.
When the medium is an emulsion, this emulsion comprises,
for example, a dispersed or continuous phase that may
comprise water, C1-C4 aliphatic alcohols and mixtures
thereof and an anhydrous organic phase comprising the
monomer. In the case of capsules or microcapsules, the
capsule may comprise the monomer in an anhydrous
medium and may be dispersed in an anhydrous medium as
defined above, water, C1-C4 aliphatic alcohols, and mixtures
thereof.
[0264] Polymerization inhibitors, such as anionic and/or
free-radical polymerization inhibitors may also be intro-
duced into the compositions, in order to enhance the stability
of the composition over time. In a non-limiting manner, the
following polymerization inhibitors may be mentioned: sul-
fur dioxide, nitric oxide, boron trifluoride, hydroquinone and
derivatives thereof such as hydroquinone monoethyl ether,
tert-butylhydroquinone (TBHQ), benzoquinone and deriva-
tives thereof such as duroquinone, catechol and derivatives
thereof such as t-butylcatechol and methoxycatechol, ani-
sole and derivatives thereof such as methoxyamsole or
hydroxyanisole, pyrogallol and derivatives thereof, p-meth-
oxyphenol, hydroxybutyltoluene, alkyl sulfates, alkyl
sulfites, alkyl sulfones, alkyl sulfoxides, alkyl sulfides, mer-
captans and 3-sulfonene, and mixtures thereof. According to
at least one embodiment, the alkyl groups contain 1 to 6
carbon atoms.
US 2008/0038218 A1
[0265] According to another embodiment, mineral or
organic acids may also be used as an inhibitor.
[0266] Thus, the cosmetic composition as disclosed herein
may also comprise at least one mineral or organic acid,
where according to at least one embodiment, the acid
comprises at least one carboxylic or sulfonic groups, with a
pKa that ranges from 0 to 6, such as phosphoric acid,
hydrochloric acid, nitric acid, benzenesulfonic acid, tolu-
enesulfonic acid, sulfuric acid, carbonic acid, hydrofluoric
acid, acetic acid, formic acid, propionic acid, benzoic acid,
mono-, di- or trichloroacetic acid, salicylic acid, trifluoro-
acetic acid, octanoic acid, heptanoic acid and hexanoic acid.
[0267] According to at least one embodiment, acetic acid
is used.
[0268] The concentration of inhibitor in the cosmetic
composition of the present disclosure may range from 10
ppm to 30% by weight for instance, from 10 ppm to 15% by
weight relative to the total weight of the composition.
[0269] To modify the anionic polymerization kinetics, it is
also possible to increase the nucleophilicity of the fiber via
chemical conversion of the keratin material.
[0270] Examples that may be mentioned include but are
not limited to the reduction of the disulfide bridges of which
keratin is partly composed, into thiols, before applying the
composition of the present disclosure. In a non-exhaustive
manner, as reducing agents for the disulfide bridges of which
keratin is partially composed, non-limiting mention may be
made of the following compounds:
[0271] anhydrous sodium thiosulfate,
[0272] powdered sodium metabisulfite,
[0273] thiourea,
[0274] ammonium sulfite,
[0275] thioglycolic acid,
[0276] thiolactic acid,
[0277] ammonium thiolactate,
[0278] glyceryl monothioglycolate,
[0279] ammonium thioglycolate,
[0280] thioglycerol,
[0281] 2,5-dihydroxybenzoic acid,
[0282] diammonium dithioglycolate,
[0283] strontium thioglycolate,
[0284] calcium thioglycolate,
[0285] zinc formosulfoxylate,
[0286] isooctyl thioglycolate,
[0287] dl-cysteine, and
[0288] monoethanolamine thioglycolate.
[0289] The composition of the present disclosure may also
comprise at least one polymer with no reactivity on the at
least one cyanoacrylate monomer and which is capable of
increasing the viscosity of the composition. Increasing the
viscosity makes it possible to reduce the rate of polymer-
ization of the cyanoacrylate monomers. To do this, it is
Feb. 14, 2008
possible to add to the composition of the present disclosure,
in a non-exhaustive manner, polymethyl methacrylate
(PMMA) or cyanoacrylate-based copolymers as described
in U.S. Pat. No. 6,224,622.
[0290] The compositions in accordance with the present
disclosure may also contain at least one agent usually used
in cosmetics, for instance reducing agents, fatty substances,
plasticizers, softeners, antifoams, moisturizers, pigments,
clays, mineral fillers, UV-screening agents, mineral colloids,
peptizers, solubilizing agents, fragrances, preserving agents,
anionic, cationic, nonionic or amphoteric surfactants, fixing
or non-fixing polymers, proteins, vitamins, direct dyes or
oxidation dyes, nacreous agents, propellent gases, mineral or
organic thickeners such as benzylidene sorbitol and N-acy-
lamino acids, oxyethylenated or non-oxyethylenated waxes,
parafiins, and C10-C30 fatty amides such as lauric diethano-
lamide, and mixtures thereof.
[0291] The compositions may be in various galenical
forms such as a lotion, an aerosol mousse, a hair conditioner
or a shampoo, a gel or a wax. The compositions may be
contained, for example, in a pump-dispenser bottle or an
aerosol spray. The compositions of the present disclosure,
after application, may be rinsed out or left in.
[0292] When the composition is contained in an aerosol, it
may comprise at least one propellant. The at least one
propellant may be chosen from compressed or liquefied
gases usually used for the preparation of aerosol composi-
tions. Air, carbon dioxide, compressed nitrogen and a
soluble gas such as dimethyl ether, halogenated or non-
halogenated hydrocarbons (butane, propane or isobutane),
and mixtures thereof may be used, for example.
[0293] According to the process of the present disclosure,
the composition as disclosed herein may be applied to the
keratin fibers, for instance human keratin fibers such as the
hair, in the presence of at least one nucleophilic agent.
[0294] According to at least one embodiment of the pro-
cess of the present disclosure, the at least one nucleophilic
agent capable of initiating the polymerization of the elec-
trophilic monomer may be applied beforehand to the keratin
fibers. The at least one nucleophilic agent may be used pure,
as a solution, in the form of an emulsion or may be
encapsulated. It may also be added to the anhydrous com-
position at the time of use just before application to the
keratin fibers.
[0295] According to at least one embodiment, the at least
one nucleophilic agent is water. This water may be supplied,
for example, by premoistening the keratin fibers. It may also
be added directly to the composition before application.
[0296] According to another embodiment, it is possible to
modify the polymerization kinetics by premoistening the
fiber with an aqueous solution whose pH has been adjusted
using a base, an acid or an acid/base mixture. The acid
and/or the base may be mineral or organic.
[0297] According to one variant, the treatment process
comprises a step of applying a composition (A) comprising
at least one fluoro compound and optionally at least one
nucleophilic agent, followed by a step of applying to the
fibers at least one composition (B), comprising at least one
electrophilic monomer, one and/or the other of the compo-
sitions containing at least one liquid organic solvent.
US 2008/0038218 A1
[0298] Alternatively, the at least one nucleophilic agent
may also be in a separate composition.
[0299] According to yet another variant, the process for
treating the keratin fibers may be a hair dyeing process,
which may be performed in several steps: a first step that
comprises applying a first composition comprising the at
least one pigment to the fibers and a second step that
comprises applying a second composition comprising, inter
alia, at least one electrophilic monomer, at least one fluoro
compound and at least one liquid organic solvent as defined
above, the at least one nucleophilic agent being optionally
present in the composition comprising the pigment or in a
separate composition.
[0300] According to at least one embodiment, the cos-
metic composition comprising the at least one pigment is an
aqueous dispersion of pigments, which allows moistening of
the fiber and initiation of the polymerization when the
composition comprising the at least one electrophilic mono-
mer, the at least one fluoro compound and the at least one
liquid organic solvent is applied.
[0301] According to the process of the present disclosure,
at least one embodiment comprises applying the at least one
electrophilic monomer, the at least one fluoro compound and
optionally the at least one pigment in the same composition.
[0302] The process of the present disclosure may comprise
additional intermediate and/or final steps such as the appli-
cation of a cosmetic product, a rinsing step and/or a drying
step. The drying may be performed under a hood, with a
hairdryer and/or with a smoothing iron. For instance, the
application of the compositions in accordance with the
present disclosure may be followed by rinsing.
[0303] It is also possible to perform multiple applications
of the composition as disclosed herein in order to obtain a
superposition of coats to achieve specific properties of the
deposit in terms of chemical nature, mechanical strength,
thickness, appearance or feel.
[0304] The present disclosure also relates to the use of a
cosmetic composition as described above for treating the
hair.
[0305] According to at least one embodiment, when the
cosmetic composition does not comprise pigments, the
cosmetic composition may be used for conditioning the hair.
[0306] According to another embodiment, the cosmetic
composition comprises both the at least one fluoro com-
pound and at least one pigment, thus the said composition
may be used for coloring the hair and optionally for condi-
tioning it.
[0307] Another aspect of the present disclosure is a multi-
compartment device or kit, comprising at least one first
compartment comprising a first composition (C) comprising
the at least one electrophilic monomer as defined herein, and
at least one second compartment comprising a second com-
position (D) comprising at least one organofluorine com-
pound, with the exception of polytetrafluoroethylene, and
pigments coated with fluoro compounds, one and/or the
other of the compositions comprising at least one liquid
organic solvent as defined above, one of the two, or both of
the compositions possibly comprising at least one cosmetic
additive as defined above.
Feb. 14, 2008
[0308] Other than in the operating examples, or where
otherwise indicated, all numbers expressing quantities of
ingredients, reaction conditions, and so forth used in the
specification and claims are to be understood as being
modified in all instances by the term “about.” Accordingly,
unless indicated to the contrary, the numerical parameters set
forth in the specification and attached claims are approxi-
mations that may vary depending upon the desired proper-
ties sought to be obtained by the present disclosure. At the
very least, and not as an attempt to limit the application of
the doctrine of equivalents to the scope of the claims, each
numerical parameter should be construed in light of the
number of significant digits and ordinary rounding
approaches.
[0309] Notwithstanding the numerical ranges and param-
eters setting forth the broad scope of the disclosure are
approximations, the numerical values set forth in the specific
examples are reported as precisely as possible. Any numeri-
cal value, however, inherently contains certain errors nec-
essarily resulting from the standard deviation found in its
respective testing measurement.
[0310] The examples that follow are intended to illustrate
the present disclosure without, however, being limiting in
nature.
EXAMPLES
Example 1
[0311] A styling composition according to the present
disclosure was prepared from the following compounds:
(1,0)-Dihydroxylated polydimethylsiloxane/ 45 g
cyclopentadimethylsiloxane (14.7/85.3) sold by Dow
Corning under the name DC 1501 Fluid
Cyclopentadimethylsiloxane sold by Dow Corning under 42.75 g
the name DC245 Fluid
Perfluoro polymethyl isopropyl ether sold by Solvay under 2 g
the name Fomblin HC 25
Methylheptyl cyanoacrylate from Chemence 10 g
Acetic acid 0.25 g
[0312] 0.2 g of the composition was applied to a lock of
1 g of clean, wet hair. After a leave-on time of 15 minutes,
the lock was dried with a hairdryer for 2 minutes. The
resultant lock had hairs that were individualized with a
pleasant, remanent texture.
Example 2
[0313] A styling composition according to the present
disclosure was prepared from the following compounds:
DC 1501 Fluid 45 g
DC 245 Fluid 42.75 g
Perfluorophenanthrene sold by F2 Chemical under 2 g
the name Flutec PC11
Methylheptyl cyanoacrylate from Chemence 10 g
Acetic acid 0.25 g
[0314] 0.2 g of the composition was applied to a lock of
1 g of clean, wet hair. After a leave-on time of 15 minutes,
US 2008/0038218 Al
the lock was dried with a hairdryer for 2 minutes. The
resultant lock had hairs that were individualized with a
pleasant, remanent texture.
Example 3
[0315] A styling composition according to the present
disclosure was prepared from the following compounds:
DC 1501 Fluid 45 g
DC 245 Fluid 42.75 g
Perfluorononyl dimethicone sold by Phoenix Chemical under 2 g
the name Pecosil FSL-150
Methylheptyl cyanoacrylate from Chemence 10 g
Acetic acid 0.25 g
[0316] 0.2 g of the composition was applied to a lock of
l g of clean, wet hair. After a leave-on time of 15 minutes,
the lock was dried with a hairdryer for 2 minutes. The
resultant lock had hairs that were individualized with a
pleasant, remanent texture.
Example 4
[0317] A styling composition according to the present
disclosure was prepared from the following compounds:
DC 245 Fluid 84.75 g
Perfluorononyl dimethicone sold by Phoenix Chemical under 5 g
the name Pecosil FSU-300
Methylheptyl cyanoacrylate from Chemence 10 g
Acetic acid 0.25 g
[0318] 0.2 g of the composition was applied to a lock of
l g of clean, wet hair. After a leave-on time of 15 minutes,
the lock was dried with a hairdryer for 2 minutes. The
resultant lock had hairs that were individualized with a
pleasant, remanent texture.
Example 5
[0319] A styling composition according to the present
disclosure was prepared from the following compounds:
DC 1501 Fluid 45 g
DC 245 Fluid 42.75 g
Trifluoropropyl dimethicone sold by Dow Coming under 2 g
the name FS-1265 Fluid
Methylheptyl cyanoacrylate from Chemence 10 g
Acetic acid
[0320] 0.2 g of the composition was applied to a lock of
l g of clean, wet hair. After a leave-on time of 15 minutes,
the lock was dried with a hairdryer for 2 minutes. The
resultant lock had hairs that were individualized with a
pleasant, remanent texture.
Feb. 14, 2008
Example 6
[0321]
Composition A was prepared from the following ingredients:
Caltafluor UH Liquid sold by Clariant 10 g
Water 90 g
Composition B was prepared from the following ingredients:
DC 1501 Fluid 45 g
DC 245 Fluid 44.75 g
Methylheptyl cyanoacrylate from Chemence 10 g
Acetic acid 0.25 g
[0322] 0.3 g of composition (A) was applied to a lock of
l g of clean, wet hair. 0.2 g of composition (B) was then
applied to this lock. After a leave-on time of 15 minutes, the
lock was dried with a hairdryer for 2 minutes. The resultant
lock had hairs that were individualized with a pleasant,
remanent texture.
Example 7
[0323] Composition (A) was prepared from the following
ingredients:
Foraperle 321 sold by DuPont de Nemou.rs 20 g
Water 80 g
[0324] Composition (B) was prepared from the following
ingredients:
DC 1501 Fluid 45 g
DC 245 Fluid 44.75 g
Methylheptyl cyanoacrylate from Chemence 10 g
Acetic acid 0.25 g
[0325] 0.3 g of composition (A) was applied to a lock of
l g of clean, wet hair. 0.2 g of composition (B) was then
applied to this lock. After a leave-on time of 15 minutes, the
lock was dried with a hairdryer for 2 minutes. The resultant
lock had hairs that were individualized with a pleasant,
remanent texture.
Example 8
[0326] A dye composition according to the present disclo-
sure was prepared from the following compounds:
DC 1501 Fluid 40 g
DC 245 Fluid 37.75 g
Mica nacre coated with brown iron oxide, sold by Eckait 10 g
under the name Prestige Bronze
Perfluoro polymethyl isopropyl ether sold by Solvay under 2 g
the name Fomblin HC 25
Methylheptyl cyanoacrylate from Chemence 10 g
Acetic acid 0.25 g
US 2008/0038218 A1
[0327] 0.5 g of the composition was applied to a lock of
1 g of clean, wet hair. After a leave-on time of 15 minutes,
the lock was dried under a hairdryer for 2 minutes. The
resultant lock had hairs that were individualized with a
pleasant, remanent texture.
Example 9
[0328] A dye composition according to the present disclo-
sure was prepared from the following compounds:
DC 1501 Fluid 40 g
DC 245 Fluid 37.75 g
Mica nacre coated with brown iron oxide, sold by Eckart 10 g
under the name Prestige Bronze
Perfluoro polymethyl isopropyl ether sold by Solvay under 2 g
the name Fomblin HC 25
Methylheptyl cyanoacrylate from Chemence 10 g
Acetic acid 0.25 g
[0329] 0.5 g of the composition was applied to a lock of
1 g of clean, wet hair. After a leave-on time of 15 minutes,
the lock was dried under a hairdryer for 2 minutes. The
resultant lock had hairs that were individualized with a
pleasant, remanent texture.
Example 10
[0330] A dye composition according to the present disclo-
sure was prepared from the following compounds:
DC 1501 Fluid 40 g
DC 245 Fluid 37.75 g
Mica nacre coated with brown iron oxide, 10 g
sold by Eckatt under the name Prestige Bronze
Perfluorophenanthrene sold by F2 Chemical 2 g
under the name Flutec PC11
Methylheptyl cyanoacrylate from Chemence 10 g
Acetic acid 0.25 g
[0331] 0.5 g of the composition was applied to a lock of
1 g of clean, wet hair. After a leave-on time of 15 minutes,
the lock was dried under a hairdryer for 2 minutes. The
resultant lock had hairs that were individualized with a
pleasant, remanent texture.
Example 11
[0332] A dye composition according to the present disclo-
sure was prepared from the following compounds:
DC 1501 Fluid 40 g
DC 245 Fluid 37.75 g
Mica nacre coated with brown iron oxide, sold by 10 g
Eckatt under the name Prestige Bronze
Perfluorononyl dimethicone sold by Phoenix Chemical 2 g
under the name Pecosil FSL-150
Methylheptyl cyanoacrylate from Chemence 10 g
Acetic acid 0.25 g
[0333] 0.5 g of the composition was applied to a lock of
1 g of clean, wet hair. After a leave-on time of 15 minutes,
Feb. 14, 2008
the lock was dried under a hairdryer for 2 minutes. The
resultant lock had hairs that were individualized with a
pleasant, remanent texture.
Example 12
[0334] A dye composition according to the present disclo-
sure was prepared from the following compounds:
DC 1501 Fluid 40 g
DC 245 Fluid 37.75 g
Mica nacre coated with brown iron oxide, sold by 10 g
Eckatt under the name Prestige Bronze
Trifluoropropyl dimethicone sold by Dow Corning 2 g
under the name FS-1265 Fluid
Methylheptyl cyanoacrylate from Chemence 10 g
Acetic acid 0.25 g
[0335] 0.5 g of the composition was applied to a lock of
1 g of clean, wet hair. After a leave-on time of 15 minutes,
the lock was dried under a hairdryer for 2 minutes. The
resultant lock had hairs that were individualized with a
pleasant, remanent texture.
Example 13
[0336] Composition (A) was prepared from the following
ingredients:
Cartafluor UH Liquid sold by Clariant 10 g
Water 90 g
[0337] Composition (B) was prepared from the following
ingredients:
DC 1501 Fluid 40 g
DC 245 Fluid 39.75 g
Mica nacre coated with brown iron oxide, 10 g
sold by Eckatt under the name Prestige Bronze
Methylheptyl cyanoacrylate from Chemence 10 g
Acetic acid 0.25 g
[0338] 0.3 g of composition A was applied to a lock of 1
g of clean, wet hair. 0.5 g of composition B was then applied
to this lock. After a leave-on time of 15 minutes, the lock
was dried with a hairdryer for 2 minutes. The resultant lock
had hairs that were individualized with a pleasant, remanent
texture.
What is claimed is:
1. A cosmetic composition for treating keratin fibers,
comprising:
at least one liquid organic solvent;
at least one electrophilic monomer; and
at least one organofluorine compound comprising at least
4 carbon atoms, with the exception of polytetrafluoro-
ethylene, and pigments coated with fluoro compounds.
US 2008/0038218 A1
17
2. The cosmetic composition according to claim 1,
wherein the at least one electrophilic monomer is chosen
from those of formula (I):
(1)
Rl IU
R2 R4
wherein:
R1 and R2 are chosen from, independently of each other,
sparingly or non- electron-withdrawing groups, and
R3 and R4 are chosen from, independently of each other,
electron-withdrawing groups.
3. The cosmetic composition according to claim 2,
wherein the at least one electrophilic monomer of formula
(I) is such that:
R1 and R2, independently of each other, are chosen from
hydrogen, saturated and unsaturated, linear, branched
and cyclic hydrocarbon-based groups that optionally
comprise at least one entity chosen from nitrogen,
oxygen and sulfur, and are optionally substituted with
at least one entity chosen from —OR, —COOR,
—COR, —SH, —SR, —OH, and halogens;
R is chosen from saturated and unsaturated, linear,
branched and cyclic hydrocarbon-based groups that
optionally comprise at least one entity chosen from
nitrogen, oxygen and sulfur, and is optionally substi-
tuted with at least one entity chosen from —OR',
COOR', COR‘, SH, SR‘ and OH, halogens,
or a polymer residue; and
R‘ is a C1-C10 alkyl radical.
4. The cosmetic composition according to claim 2,
wherein the at least one electrophilic monomer of formula
(I) is such that:
R3 and R4, independently of each other, are chosen from:
—N(R)3*, —S(R)2", —SH2*, —NH3*, —NO2,
SOZR, CEN, COOH, COOR, %OSR,
%ONH2, —CONHR, —F, £1, —Br, —I, —OR,
—COR, —SH, —SR and —OH groups, linear and
branched alkenyl groups, linear and branched alkynyl
groups, C1-C4 mono- and/or polyfluoroalkyl groups,
and aryl and/or aryloxy groups;
R is chosen from saturated and unsaturated, linear,
branched and cyclic hydrocarbon-based groups that
optionally comprises at least one entity chosen from
nitrogen, oxygen and sulfur, and is optionally substi-
tuted with at least one entity chosen from —OR',
COOR', COR‘, SH, SR‘, OH, halogens,
and polymer residues; and
R‘ is a C1-C10 alkyl radical.
5. The cosmetic composition according to claim 1,
wherein the at least one electrophilic monomer is a
cyanoacrylate monomer chosen from those of formula (11):
Feb. 14, 2008
(H)
Rl CN
R2 COXR'3
wherein:
X is chosen from NH, S and O;
R'3 is chosen from a hydrogen atom and R;
R is chosen from saturated and unsaturated, linear,
branched and cyclic hydrocarbon-based groups that
optionally comprise at least one entity chosen from
nitrogen, oxygen and sulfur, and is optionally substi-
tuted with at least one entity chosen from —OR',
%OOR', %OR', —SH, —SR', —OH, halogens,
and polymer residues; and
R1 and R2, independently of each other, are chosen from
a hydrogen atom, saturated and unsaturated, linear,
branched and cyclic hydrocarbon-based groups that
optionally comprise at least one entity chosen from
nitrogen, oxygen and sulfur, and are optionally substi-
tuted with at least one entity chosen from —OR,
COOR, COR, SH, SR, OH, and halogens.
6. The cosmetic composition according to claim 2,
wherein the at least one electrophilic monomer according to
formula (I) is such that R1 and R2 are hydrogen atoms.
7. The cosmetic composition according to claim 1,
wherein the at least one electrophilic monomer is a
cyanoacrylate monomer chosen from those of formula (V):
(V)
Rl CN
R2 COOR'3
wherein:
R'3 is chosen from C1-C10 alkyl, (C1-C4)alkoxy(C1-
C1O)alkyl and C2-C10 alkenyl radicals; and
R1 and R2, independently of each other, are chosen from
a hydrogen atom, saturated and unsaturated, linear,
branched and cyclic hydrocarbon-based groups that
optionally comprise at least one entity chosen from
nitrogen, oxygen and sulfur, and are optionally substi-
tuted with at least one entity chosen from —OR,
COOR, COR, SH, SR, OH, and halogens.
8. The cosmetic composition according to claim 7,
wherein R'3 is chosen from C6-C10 alkyl radicals.
9. The cosmetic composition according to claim 7,
wherein R1 and R2 are hydrogen atoms.
10. The cosmetic composition according to claim 1,
wherein the at least one electrophilic monomer is an alkyl
cyanoacrylate chosen from those of formula (V I):
US 2008/0038218 A1
(V1)
H CN
H COOR'3
wherein:
R'3 is chosen from:
—(CH2)7~CH3;
%H(CH3)—(CH2)5—CH3;
%H2%H(C2H5)—(CH2)3%H3;
—(CH2)5—CH(CH3)—CH3; and
—(CH2)4—CH(C2H5)%H3.
11. The cosmetic composition according to claim 1,
wherein the at least one electrophilic monomer is a
cyanoacrylate monomer and is covalently bonded to at least
one support chosen from polymers, oligomers and dendrim-
ers.
12. The cosmetic composition according to claim 1,
wherein the at least one fluoro compound is a fluorosilicone
compound chosen from those of formula (V 11):
(VII)
R1 R1 (EH3 R1
I I I
R2—si—o Ti—o Ti—o T1—R2
R1 R1 R R1
m I
Rf
wherein:
R is chosen from C1-C6 linear and branched divalent alkyl
groups;
Rf is chosen from fluoroalkyl radicals;
R1 is chosen from, independently of each other, C1-C20
alkyl radicals, hydroxyl radicals, and phenyl radicals;
R2 is R1 or Rf;
m is chosen from 0 to 500; and
n is chosen from 1 to 1000.
13. The cosmetic composition according to claim 12,
wherein the groups R1 are identical and are methyl radicals.
14. The cosmetic composition according to claim 1,
wherein the at least one fluoro compound is chosen from the
perfluorocycloalkyls of formula (V 111):
(V111)
/W
(CF2)n [CF — (CF2)p — Flm
Feb. 14, 2008
wherein:
n is equal to 3, 4 or 5;
m is equal to 1 or 2; and
p is equal to 0, 1, 2 or 3;
with the proviso that when m=2, the groups are not
necessarily alpha to each other.
15. The cosmetic composition according to claim 1,
wherein the at least one fluoro compound is chosen from the
fluoroalkyl or heterofluoroalkyl compounds chosen from
those of formula (IX):
CH3—(CH2)1_—[Z]1—X—CF3 (IX)
wherein:
t is 0 or 1;
nis0,1,2or3;
X is a linear or branched divalent perfluoroalkyl radical
containing from 2 to 5 carbon atoms; and
Z is chosen from O, S and NR, where R is chosen from
a hydrogen, (CH2)n CH3 and (CF2)m CF3 radi-
cals, where m is 2, 3, 4 or 5.
16. The cosmetic composition according to claim 1,
wherein the at least one fluoro compound is a perfluoroal-
kane chosen from those of formula Oi):
cF3—n4F3 (X)
where n ranges from 2 to 16.
17. The cosmetic composition according to claim 1,
wherein the at least one fluoro compound is chosen from the
perfluoropolyethers of formulae Oil) and Gill):
(X1)
CF3
F—[—c1=—c1=2—o—];c1=2—c1=3
where n ranges from 7 to 30; and
(X11)
CF3
CF3—[-O—CF—CF2-]m—[-O—CF2-]p—OCF3
where the ratio n1/p ranges from 20 to 40, and the
molecular weight ranges from 500 to 20,000.
18. The cosmetic composition according to claim 1,
wherein the at least one fluoro compound is chosen from the
perfluoromorpholine deriVatiVes of formula (X111):
(X111)
R
A
FZC on
I
F2C\O/CF2
where R is chosen from C1-C4 perfluoroalkyl radicals.
19. The cosmetic composition according to claim 1,
wherein the at least one fluoro compound is chosen from the
fluoro esters of formula OHV):
US 2008/0038218 A1
19
(XIV)
CF3-(CF2)c—(CH2)d—0—C—A—C—0—(CH2)d—(CF2)c—CF3
II II
0 R40
wherein:
R4 is a hydrogen atom or a radical
:C—0—(CH2)d—(CF2)c—CF3,
O
A is chosen from linear and branched, optionally
hydroxylated, C1-C18 alkylene and alkenylene chains,
c is l to 17, and
d is l to 18.
20. The cosmetic composition according to claim 1,
wherein the at least one fluoro compound is chosen from the
perfluoroalkylpolyacrylate-based copolymers that can be
obtained by polymerization using:
(i) a monomer of acrylic type or of acrylamide type
chosen from those of formula (A'):
(A')
H2c—|—"—X—(Y)Z—R5
R40
wherein:
R4 is chosen from a hydrogen atom and C1-C4 alkyl
radicals,
X is chosen from O and —N—R2, where R2 is chosen
from a hydrogen atom and C1-C10 alkyl and hydroxy-
alkyl radicals,
Y is chosen from C1-C6 alkylene radicals,
z is equal to 0 or 1,
R5 is chosen from linear and branched C1-C20 alkyl
radicals, all or some of the hydrogen atoms of which
are replaced with fluorine atoms, or a radical compris-
ing perfluoropolyether groups;
(ii) a monomer of the type B‘ chosen from those of
formula (B'):
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