WO2011089985A1 - Composition cosmétique pour les fibres de kératine - Google Patents

Composition cosmétique pour les fibres de kératine Download PDF

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Publication number
WO2011089985A1
WO2011089985A1 PCT/JP2011/050590 JP2011050590W WO2011089985A1 WO 2011089985 A1 WO2011089985 A1 WO 2011089985A1 JP 2011050590 W JP2011050590 W JP 2011050590W WO 2011089985 A1 WO2011089985 A1 WO 2011089985A1
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Prior art keywords
group
chosen
keratin fibers
radical
cosmetic composition
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PCT/JP2011/050590
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English (en)
Inventor
Boni Maxime De
Francoise Pataut
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L'oreal
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Publication of WO2011089985A1 publication Critical patent/WO2011089985A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/95—Involves in-situ formation or cross-linking of polymers

Definitions

  • the present invention relates to a cosmetic composition for keratin fibers such as hair.
  • the present relates to a cosmetic composition for keratin fibers such as hair.
  • the present is a cosmetic composition for keratin fibers such as hair.
  • invention relates to a cosmetic composition for keratin fibers which provides the keratin fibers with good reshaping or
  • keratin fibers such as hair consists, in a first step, in opening the keratin disulfide bonds (cystine) with a composition comprising a reducing agent, and preferably after rinsing the keratin fibers, in reforming, in a second step, said disulfide bonds by applying to the keratin fibers which have been placed beforehand under tension with curlers or equivalents thereof, or which have been straightened by other means,- an oxidizing
  • composition also called a fixing agent, so as to give the desired form to the keratin fibers.
  • This method enables either the waving of the keratin fibers or the decurling, the backcombing or the straightening thereof.
  • the reducing agents usually used during the first step comprise thiol-based reducing agents such as thioglycolic acid and
  • cysteine as well as non thiol-based reducing agents such as sulfites and bisulfites.
  • JP-A-2008-260750 discloses a method for permanent waving of keratin fibers such as hair by using a reducing composition which may include a thiol-based or non-thiol based reducing agent.
  • the cosmetic , roperties of the keratin fibers sometimes become worse when the keratin fibers are subjected to shampooing.
  • hair relaxers which can relax or straighten naturally curly or kinky hair. Hair relaxers may either be applied in a hair salon by a professional or in the home by an individual consumer.
  • Hair fiber is a keratinous material which is comprised of
  • a disulfide bond may be formed from the reaction of two sulfhydryl groups (-SH) , one on each of two cysteine residues, which results in the formation of a cystine residue. While there maybe other types of bonds between the polypeptides in hair fibers, such as ionic bonds, the permanent curling and the shape of the hair is essentially dependent on the disulfide bonds of cystine residues.
  • hair relaxing processes are chemical processes which may alter the aforementioned disulfide bonds between polypeptides in hair fibers and may form lanthionine residues [S[CH 2 CH(NH- ) (CO-)] 2 ].
  • lanthionizing is used when one skilled in the art refers to the relaxing or straightening of keratin fibers by hydroxide ions.
  • hair fibers may be relaxed or straightened by disrupting the disulfide bonds of the hair- fibers with an
  • alkaline agent The chemical disruption of disulfide bonds with such an alkaline agent is generally combined with mechanical straightening of the hair, such as combing, and straightening generally occurs due to changes in the relative positions of neighboring polypeptide chains within the hair fiber.
  • This reaction is generally terminated by rinsing and/or application of a neutralizing composition.
  • the reaction with the alkaline agent is normally initiated by available hydroxide ions, as shown in, for example, JP-A-2004- 256535 (US-A-2004-166073) .
  • available hydroxide ions are hydroxide ions which are available for lanthionization .
  • reaction sequences that are predominantly used in the art to explain the disruption of the disulfide bonds in hair fibers by available hydroxide ions. Both of these reaction sequences result in lanthionine residue formation.
  • One reaction sequence comprises at least one
  • the second reaction sequence comprises at least one ⁇ -elimination reaction initiated by the nucleophilic attack of an available hydroxide ion on a hydrogen atom bonded to a carbon atom in the ⁇ -position with respect to the disulfide bond of a cystine residue. See Zviak. The result is the formation of a dehydroalanine residue.
  • the dehydroalanine residue then reacts with either the thiol group of a cysteine residue or the amino group of an alanine residue to form a lanthionine residue or a lysinoalanine residue, respectively.
  • These stable irreversible crosslinks in the treated hair make subsequent chemical relinking of the polypeptides unnecessary.
  • the only step that may be required following a straightening process using such hydroxide-containing alkaline agents is the removal of any excess alkaline solution to avoid and minimize damage to the hair
  • an acidic shampoo may be used to neutralize residual alkali and remove it from the hair and scalp.
  • alkaline agents such as guanidine hydroxide
  • hydroxide-based straighteners do not have a highly objectionable odor or cause such an odor upon treating the hair.
  • relaxers including hydroxide ions typically cause damage to keratin fibers, and often result in poor cosmetic properties such as a dry and coarse appearance and feel to the touch of the keratin fibers .
  • the cosmetic properties of the keratin fibers sometimes become worse when the keratin fibers are subjected to shampooing .
  • An objective of the present invention is to reduce the damage to keratin fibers due to permanent reshaping or deforming , of the keratin fibers, and to provide the keratin fibers with good cosmetic properties in terms of, for example, softness,
  • the keratin fibers should have good permanent reshaping or deforming properties.
  • a cosmetic composition for keratin fibers comprising (a) at least one alkoxysilane, (b) at least one silicone, and (c) at least one reshaping or deforming agent selected from the group consisting of thiol-based reducing agents, non thiol-based reducing agents, alkaline metal hydroxides and alkaline earth metal hydroxides.
  • the alkoxysilane in the cosmetic composition according to the present invention comprise at least one solubilizing group.
  • the alkoxysilane comprising at least one solubilizing group may be represented by the formula:
  • R 1 denotes a halogen atom, an -OR 11 group or a -R 12 group
  • R 2 denotes a halogen atom, an -OR 21 group or a -R 22 group
  • R 3 denotes a halogen atom, an -OR 31 group or a -R 32 group,
  • R 4 denotes a group bearing at least one functional group chosen from the group consisting of carboxylic acids and salts thereof, sulfonic acids and salts thereof, amines and salts thereof, amino acids and salts thereof, and polyalkylethers ;
  • R 11 , R 21 , R 31 , R 12 , R 22 and R 32 which may be identical or different, are chosen from linear and branched, saturated and unsaturated, C 1 -C14 hydrocarbon groups, optionally bearing at least one additional chemical function chosen from carboxylic acids and salts thereof, sulfonic acids and salts thereof, amines and salts thereof, amino acids and salts thereof, and polyalkylethers, where R 11 , R 21 and R 31 may also be chosen from hydrogen and at least two groups of R 11 , R 21 and R 31 are not hydrogen.
  • alkoxysilane comprising at least one solubilizing group be represented by the formula:
  • R 11 , R 21 and R 31 which may be identical or different, are chosen from linear and branched, saturated and unsaturated, Ci-C 6
  • hydrocarbon groups optionally bearing at least one additional chemical function chosen from carboxylic acids and salts thereof, sulfonic acids and salts thereof, amines and salts thereof, amino acids and salts thereof, and polyalkylethers; and
  • n denotes an integer from 1 to 6.
  • the alkoxysilane ( s ) may be present in the cosmetic composition according to the present invention in an amount of 0.1 to 20% by weight relative to the total weight of the cosmetic composition.
  • the silicone be chosen from the group consisting of
  • polydial kylsiloxanes polydial kylsiloxanes , polyalkylarylsiloxanes, polydiarylsiloxanes, and organomodified polysiloxanes .
  • organomodified polysiloxanes organomodified
  • polysiloxanes may be chosen from polydialkylsiloxanes
  • the silicone (s) may be present in the cosmetic composition
  • the thiol-based reducing agent may be chosen from the group consisting of thioglycolic acid and' derivatives thereof, dithioglycolic acid and derivatives thereof, thiolactic acid and derivatives thereof, 3-mercaptopropionic acid and derivatives thereof, cysteamine and derivatives thereof, mono- thioglycerol and derivatives thereof, cysteine and derivatives thereof, and salts thereof.
  • the non thiol-based reducing agent may be chosen from the group consisting of sulfites, bisulfites, sulfinates, phosphines, sugars, reductones and hydrides and preferably from sulfites, bisulfites and phosphines.
  • the alkaline metal hydroxide may be selected from the group consisting of lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide, and cesium hydroxide.
  • the alkaline earth metal hydroxide may be selected from the group consisting of beryllium hydroxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide and barium hydroxide.
  • the reshaping or deforming agent (s) may be present in the
  • cosmetic composition according to the present invention in an amount of 0.1 to 15% by weight relative to the total weight of the cosmetic composition.
  • the pH of the cosmetic composition according to the present invention may range from 10 to 14, preferably 12 to 14.
  • the cosmetic composition according to the present invention is preferably intended for permanently deforming keratin fibers.
  • the present invention also relates to a kit for deforming keratin fibers, comprising:
  • first composition comprising (a) at least one alkoxysilane ; and a second composition comprising (b) at least one silicone, wherein
  • either the first composition or second composition comprises (c) at least one reshaping or deforming agent selected from the group consisting of thiol-based reducing agents, non thiol-based reducing agents, alkaline metal hydroxides and alkaline earth metal hydroxides.
  • the present invention also relates to a process for deforming keratin fibers, comprising the steps of:
  • composition comprising (a) at least one alkoxysilane, (b) at least one silicone, and (c) at least one reshaping or deforming agent selected from the group consisting of thiol-based reducing agents, non thiol-based reducing agents, alkaline metal hydroxides and alkaline earth metal hydroxides; and providing the keratin fibers with mechanical tension and/or heat, for the deformation of the keratin fibers; and
  • the above process may further comprise the step of rinsing the keratin fibers after the step of applying the composition onto the keratin fibers and/or after the step of oxidizing the keratin fibers.
  • the inventors After diligent research, the inventors have discovered that it is possible to reduce the damage to keratin fibers by permanent reshaping or deforming of the keratin fibers, and provide the keratin fibers with good cosmetic properties such as a soft or supple appearance and feel to the touch which can last for a long time even after shampooing, while providing the keratin fibers with good permanent reshaping or deforming effects, by combining at least one reshaping or deforming agent selected from the group consisting of thiol-based reducing agents, non-thiol based reducing agents, alkaline metal hydroxides and alkaline earth metal hydroxides, with at least one alkoxysilane and at least one silicone .
  • the cosmetic composition according to the present invention comprises at least one alkoxysilane, at least one silicone, and at least one reshaping or deforming agent selected from the group consisting of thiol-based reducing agents, non thiol-based reducing agents, alkaline metal hydroxides and alkaline earth metal hydroxides.
  • thiol-based reducing agents selected from the group consisting of thiol-based reducing agents, non thiol-based reducing agents, alkaline metal hydroxides and alkaline earth metal hydroxides.
  • the cosmetic composition according to the present invention includes at least one alkoxysilane.
  • the alkoxysilane comprise at least one solubilizing group.
  • Suitable solubilizing groups for use in accordance with the present invention include, but are not limited to, primary, secondary, and tertiary amine, aromatic amine, alcohol,
  • carboxylic acid sulfonic acid, anhydride, carbamate, urea, guanidine, aldehyde, ester, amide, epoxy, pyrrole,
  • solubilizing functional groups may be identical or different.
  • the alkoxysilane present in the cosmetic composition according to the present invention may comprise at least one silicon atom, preferably one silicon atom.
  • the alkoxysilane present in the cosmetic composition according to the present invention may, in at least one embodiment, comprise two or three alkoxy functions.
  • the alkoxy functional groups are chosen from methoxy and ethoxy functional groups .
  • the alkoxysilane comprising at least one solubilizing group present in the cosmetic composition according to the present invention may be chosen from compounds of formula ( I ) :
  • R 1 denotes a halogen atom, an -OR 11 group or a -R 12 group
  • R 2 denotes a halogen atom, an -OR 21 group or a -R 22 group
  • R 3 denotes a halogen atom, an -OR 31 group or a -R 32 group,
  • R 4 denotes a group bearing at least one functional group chosen from the group consisting of carboxylic acids and salts thereof, sulfonic acids and salts thereof, amines and salts thereof, amino acids and salts thereof, and polyal kylethers ;
  • R 11 , R 21 , R 31 , R 12 , R 22 and R 32 which may be identical or different, are chosen from linear and branched, saturated and unsaturated, C x -Ci4 hydrocarbon groups, optionally bearing at least one
  • R , R and R may also be chosen from hydrogen and at least two groups of R 11 , R 21 and R 31 are not hydrogen.
  • the R 11 , R 21 , R 31 , R 12 , R 22 and R 32 groups are chosen from C1-C12 alkyl groups, C 6 -Ci 4 aryl groups, Ci ⁇ Cs alkyl-C6-Ci4 aryl groups, and C6-C14 aryl-Ci-Cg alkyl groups.
  • the alkoxysilane comprising at least one solubilizing group may be chosen from the compounds represented by the
  • R 11 , R 21 and R 31 which may be identical or different, are chosen from linear and branched, saturated and unsaturated, C1-C6
  • hydrocarbon groups optionally bearing at least one additional chemical function chosen from carboxylic acids and salts thereof, sulfonic acids and salts thereof, amines and salts thereof, amino acids and salts thereof, and polyalkylethers ; and
  • n denotes an integer from 1 to 6, for example, from 2 to 4.
  • the alkoxysilane comprising at least one solubilizing group present in the cosmetic composition according to the present invention is a ⁇ - aminopropyltriethoxysi lane .
  • the alkoxysilane comprising at least one solubilizing group present in the cosmetic composition according to the present invention may be chosen from compounds of formula (II):
  • R 8 is chosen from halogen atoms, OR 1 groups, and R 81 groups;
  • R 9 is chosen from halogen atoms, OR 1 ' groups, and R 91 groups;
  • R 10 is chosen from halogen atoms, OR''' groups, and R 101 groups; R 5 , R 6 , R 7 , .R', R'', R''', R 81 , R 91 , and R 101 , which may be
  • R 5 , R 6 , R', R'', and R' 1 ' may also be chosen from hydrogen; at least two of the groups R 8 , R 9 , and R 10 are different from R 81 , R 91 , and R 101 and halogen atoms, and with corresponding groups R' and/or R 1 ', and/or R ' ' ' are not hydrogen.
  • the R 5 , R 6 , R 81 , R 91 , R 101 , R', R ' ' , and R 1 ' 1 groups are chosen from C 1 -C 12 alkyl, C e -Ci 4 aryl, Ci-Cg alkyl- C 6 -Ci4 aryl, and C 6 -Ci 4 aryl-Cx-Ce-al kyl radicals.
  • the R 7 may be chosen from C 1 .-C 12 alkylene, C e -Ci 4 arylene, Ci-C 8 alkylene-C 6 -Ci 4 arylene, and C6 ⁇ Ci 4 arylene ' -Ci-Cs-al kylene radicals.
  • the alkoxysilane comprising at least one solublizing group present in the cosmetic composition according to the present invention may be chosen from compounds of formula (III) :
  • R 13 is chosen from halogen atoms and OR' 13 groups and R 14 is chosen from halogen atoms and OR' 14 groups, wherein at least one of R 13 and R 14 is not a halogen atom;
  • R' 13 and R' 14 which may be identical or different, are chosen from hydrogen, and linear and branched, saturated and unsaturated Ci ⁇ Ci 4 hydrocarbon groups; wherein at least one of R' 13 and R' 14 is not hydrogen;
  • R 16 is a non-hydrolyzable functional group providing a cosmetic effect
  • R 15 is a non-hydrolyzable functional group bearing at least one function chosen from: amines, carboxylic acids and salts thereof, sulfonic acids and salts thereof, polyols such as glycol,
  • polyethers such as polyalkylene ether, and phosphoric acids and salts thereof.
  • the term "functional group providing a cosmetic effect” means a group derived from an entity chosen from reducing agents, oxidizing agents, coloring agents, polymers, surfactants, antibacterial agents, and UV absorbing filters.
  • the functional group providing a cosmetic effect is a group derived from a coloring agent.
  • the alkoxysilane comprising at least one solubilizing group present in the cosmetic composition according to the present invention may be chosen from. compounds of formula (IV) :
  • R 45 , R 44 , R' 45 , and R' 44 which may be identical or different, are chosen from linear. and branched, saturated and unsaturated
  • hydrocarbon chains optionally comprising at least one heteroatom, optionally interrupted by or substituted with at least one group chosen from ether, ester, amine, amide, carboxyl, hydroxyl, and carbonyl groups;
  • x is an integer ranging from 1 to 3;
  • x' is an integer ranging from 1 to 3;
  • A, A', and A' 1 which may be identical or different, are chosen from linear or branched Ci-C 2 o alkylene divalent radicals; and R 23 and R' 23 , which may be identical or different, are chosen from hydrogen and linear and branched, saturated and unsaturated hydrocarbon chains, optionally comprising at least one ⁇ heteroatom, optionally interrupted by or substituted with at least one entity chosen from: ether, Ci-C 2 o alcohol ester, amine, carboxyl,
  • R 45 , R 44 , R' 45 , and R' 44 which may be identical or different, may be chosen from hydrocarbon chains.
  • hydrocarbon chain means, for example, a chain comprising from 1 to 10 carbon atoms.
  • R 23 and R' 23 may be chosen from hydrocarbon chains.
  • the hydrocarbon chains may comprise from 1 to 10 carbon atoms.
  • the aromatic ring comprises from 6 to 30 carbon atoms. In another embodiment, the aromatic ring is an optionally substituted phenyl radical.
  • R" R' 45
  • the alkoxysilane comprising at least one solubilizing group used according to the present
  • invention may also have at least one of the following
  • R 45 , R 4 V R' 45 , and R ' 4 which may be identical or different, are chosen from C1-C4 alkyl groups;
  • a and A' which may be identical or different, are chosen from linear C1-C4 alkylene groups; and/or
  • R 23 is hydrogen
  • the alkoxysilane comprising at least one solubilizing group may be chosen from compounds of formula (V) :
  • R 24 and R 25 which may be identical or different, are chosen from linear and branched, saturated and unsaturated hydrocarbon chains, optionally comprising at least one heteroatom, optionally
  • n ' ' 0 or 1;
  • n' ' 0 or 1;
  • E and E' which may be identical or different, are chosen from linear or branched C1-C20 alkylene divalent radicals;
  • R 26 and R 27 which may be identical or different, are chosen from hydrogen and linear. and branched, saturated and unsaturated hydrocarbon chains, optionally comprising at least one heteroatom, optionally interrupted by or substituted with at least one entity chosen from: ether, Ci-C 20 alcohol ester, amine, carboxyl,
  • r is an integer ranging from 0 to 4.
  • R which may be identical or different, is chosen from hydrogen 'and linear and branched, saturated and unsaturated hydrocarbon chains, comprising, for example, from 1 to 10 carbon atoms and optionally at least one heteroatom, optionally interrupted by or substituted with at least one entity chosen from: ether, Ci-C 2 o alcohol ester, amine, carboxyl, alkoxysilane, C 6 -C 30 aryl,
  • hydroxyl, and carbonyl groups and aromatic, heterocyclic, and non-heterocyclic rings, optionally substituted with at least one group chosen from: C ! -C 2 o alcohol ester, amine, amide, carboxyl, alkoxysilane, hydroxyl, carbonyl, and acyl groups.
  • R 24 and R 25 which may be identical or different, may be chosen from hydrocarbon chains.
  • hydrocarbon chain is intended to mean a chain comprising, for example, from 1 to 10 carbon atoms.
  • R 26 and R 27 may be chosen from hydrocarbon chains.
  • the hydrocarbon chains may comprise from 1 to 10 carbon atoms.
  • the aromatic ring comprises from 6 to 30 carbon atoms.
  • the aromatic ring is an optionally substituted phenyl radical.
  • the alkoxysilane comprising at least one solubilizing group used in accordance with the present invention may have at least one of the following
  • R 24 is a Ci-C 4 alkyl group
  • R 26 and R 27 which may be identical or different, are chosen from hydrogen and groups chosen from C1-C4 alkyl groups, C1-C4
  • the alkoxysilane comprising at least one solubilizing group may be chosen from:
  • the alkoxysilane comprising at least one solubilizing group present in the cosmetic composition according to the present invention may be chosen from compounds of formula (VI):
  • R 29 and R 30 which may be identical or different, are chosen from linear or branched, saturated or unsaturated, hydrocarbon chains, optionally comprising at least one heteroatom, optionally
  • R29 and R 30 which may be identical or different, can be chosen from hydrocarbon chains.
  • hydrocarbon chain means a chain comprising, for example, from 1 to 10 carbon atoms.
  • the alkoxysilane comprising at least one solubilizing group may have at least one of the following
  • R 29 and R 30 which may be identical or different, are chosen from Ci-C ⁇ , alkyl groups;
  • ⁇ is a linear C1-C4 alkylene group.
  • the alkoxysilane comprising at least one solubilizing group may be chosen from:
  • alkoxysilanes of the invention are N-(2-aminoethoxysilanes of the invention.
  • the alkoxysilane is a ⁇ -aminopropyltriethoxysilane (APTES) .
  • APTES ⁇ -aminopropyltriethoxysilane
  • the amount of the alkoxysilane ( s ) in the cosmetic composition according to the present invention is not limited.
  • the amount of the alkoxysilane ( s ) can be 0.1 wt% to 20 wt%, preferably 0.5 wt% to 10 wt%, relative to the total weight of the cosmetic
  • the cosmetic composition according to the present invention includes at least one silicone.
  • the silicone used according to the present invention may be chosen from polydialkylsiloxanes, such as polydimethyl siloxanes (PDMS), polyalkylarylsiloxanes, polydiarylsiloxanes, and
  • organomodified-polysiloxanes comprising at least one functional moiety chosen from poly (oxyalkylene) moieties, amine moieties, alkoxy moieties, hydroxylated moieties, acyloxyalkyl moieties, carboxylic acid moieties, hydroxyacylamino moieties, acrylic moieties, polyamine moieties and oxazoline moieties, and
  • the organomodified-polysiloxanes may be preferably chosen from polydialkylsiloxanes organomodified with at least one functional group chosen from amine groups, C 1-C4 alkoxy groups, carboxyl groups, acrylic groups and polyamine groups.
  • Silicones suitable for use according to the present invention include, but are not limited to, volatile or non-volatile, cyclic, linear, or branched silicones, optionally modified with organic moieties, having a viscosity ranging from 5 ⁇ 10 ⁇ 6 to 2.5 m 2 /s at 25° C, for example, from 1*10 ⁇ 5 to 1 m 2 /s.
  • Silicones that may be used in the present invention may be any suitable silicones that may be used in the present invention.
  • soluble or insoluble in the cosmetic composition according to the present invention may be, for instance, polyorganosiloxanes that are not soluble in the cosmetic composition according to the present invention. They may be in a form chosen from fluids, waxes, resins, and gums.
  • Organopolysiloxanes are defined, for instance, by Walter NOLL in “Chemistry and Technology of Silicones” (1968), Academic Press. They may be volatile or non volatile.
  • the silicones When they are volatile, the silicones may be chosen from those having a boiling point ranging from 60°C to 260°C, for example: (i) cyclic polydialkylsiloxanes comprising from 3 to 7 silicon atoms, for instance, from 4 to 5 silicon atoms.
  • cyclic polydialkylsiloxanes comprising from 3 to 7 silicon atoms, for instance, from 4 to 5 silicon atoms.
  • Non-limiting examples of such siloxanes include the
  • octamethylcyclotetrasiloxane marketed, for instance, under the trade name VOLATILE SILICONE® 7207 by UNION CARBIDE and SILBIONE® 70045 V2 by RHODIA, the decamethylcyclopentasiloxane marketed under the trade name VOLATILE SILICONE® 7158 by UNION CARBIDE, and SILBIONE®70045 V5 by RHODIA, as well as mixtures thereof.
  • Cyclomethicones may also be used, for example, those marketed under the references DC 244, DC 245, DC 344, DC 345, and DC 246 by DOW CORNING. Cyclocopolymers of the dimethylsiloxane/methylalkylsiloxane type may also be used, such as SILICONE VOLATILE® FZ 3109 marketed by UNION CARBIDE, of formula : wherein
  • Combinations of cyclic polydialkylsiloxanes with silicon derived organic compounds may also be used, such as an
  • linear volatile polydialkylsiloxanes comprising from 2 to 9 silicon atoms and having a viscosity equal to or less than 5*10 " ⁇ m 2 /s . at 25°C.
  • a non-limiting example of such a compound is the decamethyltetrasiloxane marketed, for instance, under the trade name "SH-200" by TORAY SILICONE. Silicones belonging to this class are also described, for example, in Cosmetics and
  • the silicones may be chosen from nonvolatile silicones such as polydialkylsiloxanes,
  • polyalkylarylsiloxanes polydiarylsiloxanes, waxes, gums, silicone resins, and polyorganosiloxanes modified with the hereabove organofunctional moieties.
  • -the silicones are chosen from polydialkylsiloxanes, for example, polydimethylsiloxanes with trimethylsilyl end groups known under the trade name dimethicones .
  • the viscosity of these silicones is measured at 25°C according to ASTM 445 standard Appendix C.
  • Non limiting examples of commercial products corresponding to such polydialkylsiloxanes include:
  • SILBIONE® fluids of the series 47 and 70 047 and MIRASIL® fluids marketed by RHODIA for example the 70 047 fluid V 500 000; * fluids of the MIRASIL® series marketed by RHODIA;
  • fluids of the series 200 marketed by DOW CORNING such as DC200, with a viscosity of 60,000 mm 2 /s;
  • VISCASIL® fluids of GENERAL ELECTRIC and some fluids of the SF series (e.g., SF 96 and SF 18) of GENERAL ELECTRIC; and
  • Polydimethylsiloxanes with dimethylsilanol end groups may also be used, for example, those sold under the trade name dimethiconol (CTFA) , such as fluids of the 48 series marketed by RHODIA.
  • CTFA dimethiconol
  • Polydimethylsiloxane waxes may also be used.
  • Silicone gums suitable for use according to the present invention include, but are not limited to, polydialkylsiloxanes such as polydimethylsiloxanes having high number average molecular
  • This solvent may be chosen from volatile silicones, polydimethylsiloxane (PDMS ) fluids , polyphenylmethylsiloxane
  • PPMS polyisoparaffins
  • silicone gums may also be chosen, for example, from amodimethicones , such as the products marketed under the references DC 929 Emulsion and DC 939 Emulsion by DOW CORNING, and the Belsil ADM LOG1 product marketed by WACKER.
  • combinations of silicones may also be used, such as:
  • CTFA dimethiconol
  • CFA cyclic polydimethylsiloxane also called cyclomethicone
  • a polydimethylsiloxane gum and a cyclic silicone such as the SF 1214 Silicone Fluid product marketed by GENERAL ELECTRIC, such a product being an SF 30 gum corresponding to a dimethicone, with a number average molecular weight of 500,000 solubilized in the SF 1202 Silicone Fluid, and a product
  • mixtures of two PDMS with different viscosities for example, mixtures of a PDMS gum and a PDMS fluid, such as the SF 1236
  • the SF 1236 product is a mixture of an SE 30 gum such as that defined above with a
  • Such product may comprise 15% of an SE 30 gum and 85% of an SF 96 fluid.
  • organopolysiloxane resins suitable for use according to the - present invention include, but are not limited to, crosslinked siloxane systems comprising at least one of the following units:
  • These resins include, for example, the product marketed under the trade name “ DOW CORNING 593” and those marketed under the trade names “SILICONE FLUID SS 4230 and SS 4267” by GENERAL ELECTRIC, that are dimethyl /trimethyl siloxane structured silicones.
  • Resins of the trimethylsiloxysilicate type may also be used, for instance, those marketed under the trade names X22-4914, X21-5034, and X21-5037 by SHIN-ETSU.
  • Polyalkylarylsiloxanes may be chosen from
  • polydimethyl /methylphenyl siloxanes and linear and/or branched polydimethyl /diphenyls iloxanes with viscosities ranging from
  • Non-limiting examples of such polyalkylarylsiloxanes include the products marketed under the following trade names:
  • SILBIONE® fluids of the 70 641 series from RHODIA SILBIONE® fluids of the 70 641 series from RHODIA
  • RHODORSIL® fluids of the 70 633 and 763 series from RHODIA phenyltrimethicone fluid marketed under the reference DOW CORNING 556 COSMETIC, GRADE FLUID by DOW CORNING;
  • PK series silicones from BAYER for example, the PK20 product
  • PN PH series silicones from BAYER, for example, the PN1000 and PH1000 products
  • SF series fluids from GENERAL ELECTRIC such as SF 1023, SF 1154, SF 1250, -and SF 1265.
  • Organomodified-silicones which may be used according to the present invention include, but are not limited to, silicones such as those previously defined and comprising within their structure at least one organofunctional moiety linked by means of a
  • Organomodified silicones may include, for example,
  • polyorganosiloxanes comprising:
  • polyethyleneoxy and/or polypropyleneoxy moieties optionally comprising C 6 -C 24 alkyl moieties, such as products called
  • optionally substituted amine moieties for example, the products marketed under the trade name GP 4 Silicone Fluid and GP 7100 by GENESEE, and the products marketed under the trade names Q2 8220 and DOW CORNING, 929 and 939 by DOW CORNING.
  • Substituted amine moieties may be chosen, for example, from amino Ci-C 4 alkyl moieties.
  • Aminosilicones may have additional Ci-C 4 alkoxy functional groups, such as " those corresponding to the WACKER BELSIL ADM LOG 1 product;
  • alkoxylated moieties such as the product marketed under the trade name "SILICONE COPOLYMER F-755" by SWS SILICONES, and ABIL WAX® 2428, 2434, and 2440 by GOLDSCHMIDT;
  • hydroxylated moieties such as hydroxyalkyl function-containing polyorganosiloxanes described, for instance, in French Patent Application No. FR-A-85 163 34;
  • acyloxyalkyl moieties for example, the polyorganosiloxanes described in U.S. Pat. No. 4,957,732;
  • anionic moieties of the carboxylic acid type for example, the products described in European Patent No. 0 186 507, marketed by CHISSO CORPORATION, and carboxylic alkyl anionic moieties, such as those present in the X-22-3701E product marketed by SHIN-ETSU; 2-hydroxyalkyl sulfonate; and 2-hydroxyal kyl thiosulfate such as the products marketed by GOLDSCHMIDT under the trade names ABIL® S201 and ABIL® S255;
  • hydroxyacylamino moieties such as the polyorganosiloxanes described in European Patent Application No. 0 342 834.
  • a non- limiting example of a corresponding commercial product is the Q2- 8413 product marketed by DOW CORNING;
  • acrylic moieties such as the products marketed under the names VS80 and VS70 by 3M;
  • Silicones that may be, used according to the present invention may comprise 1 or 2 oxazoline groups, for example, poly ( 2-methyl oxazoline-b-dimethyl siloxane-b-2-methyl oxazoline) and poly (2- ethyl-2-oxazoline-dimethyl siloxane) .
  • oxazoline groups for example, poly ( 2-methyl oxazoline-b-dimethyl siloxane-b-2-methyl oxazoline) and poly (2- ethyl-2-oxazoline-dimethyl siloxane) .
  • OX-40, OS-51, OS-96, and OS-88 may also be used.
  • Suitable silicone-based celluloses which may be used according to the present invention include the products marketed by SHIN-ETSU under the references X-22-8401 and X-22-8404.
  • the silicones of the invention are organomodified- silicones. More preferably, the silicones of the invention are aminosilicones .
  • the amount of the silicone (s) in the cosmetic composition is the amount of the silicone (s) in the cosmetic composition.
  • the amount of the silicone (s) can be 0.01 wt% to 20 wt%, preferably 0.1 wt% to 5 wt%, relative to the total weight of the cosmetic composition.
  • the cosmetic composition according to the present invention includes at least one reshaping or deforming agent selected from the group consisting of thiol-based reducing agents, non thiol- based reducing agents, alkaline metal hydroxides and alkaline earth metal hydroxides.
  • a reshaping or deforming agent selected from the group consisting of thiol-based reducing agents, non thiol- based reducing agents, alkaline metal hydroxides and alkaline earth metal hydroxides.
  • the "thiol-based reducing agent” means a reducing agent with at least one thiol.
  • the thiol-based reducing agent may preferably be chosen from the group consisting of thioglycolic acid and derivatives thereof, in particular esters thereof such as
  • glycerol or glycol monothioglycolate dithioglycolic acid and derivatives thereof in particular esters thereof such as glycerol or glycol dithioglycolate ; thiolactic acid and derivatives
  • esters thereof such as glycerol
  • esters such as N-acetylcysteine, N-alkanoylcysteine and cysteine alkyl esters; and salts thereof.
  • salts mention may be made of, for example, ammonium salts; primary-, secondary- or tertiary-amihe salts; alkaline metal salts; and, alkaline earth metal salts.
  • primary-, secondary- or tertiary-amine for example, monoethanolamine , di- isopropanolamine or triethanolamine, respectively, may be
  • thiol-based reducing agent examples include, but are not limited to, sugar N-mercapto alkyl amides such as N- (mercapto-2-ethyl ) gluconamide , ⁇ - mercaptopropionic acid and derivatives thereof; thiomalic acid; pantheteine; N- (mercaptoalkyl ) ⁇ -hydroxyalkyl amides such as those described in European Patent Application No. 0 354 835 and N- mono- or N, N-dialkylmercapto 4-butyramides such as those
  • aminomercaptoalkyl amides such ' as those described in European Patent Application No. 0 432 000 and
  • alkylaminomercaptoalkylamides such as those described in European Patent Application No. 0 514 282; (2/3) hydroxy-2 propyl
  • non thiol-based reducing, agent means a reducing agent with no thiol moiety.
  • the non thiol-based reducing agent may
  • the non thiol-based reducing agent may be selected from ammonium sulfites and bisulfites as well as metal sulfites and bisulfites, more preferably alkali metal or alkali earth metal sulfites and bisulfites, and more preferably sodium sulfites and bisulfites.
  • sulfinates As the sulfinates, mention may be made of sulfinic acid salts, and benzenesulfinic acid salts such as sodium salts thereof.
  • the sulfinic acid derivatives as described in FR-A-2814948 can also be used.
  • a preferred sulfinate compound is 2-hydroxy-2- sulfinatoacetic acid, disodium salt.
  • the phosphine(s) can be chosen from the compounds of formula (VII) below:
  • L is a linker that represents a covalent bond or a divalent hydrocarbon-based radical optionally comprising one or more hetero atoms chosen from an oxygen atom, a sulfur atom, a
  • n is an integer equal to 0 or 1;
  • q is an integer equal to 1 or 2;
  • p is an integer equal to 0 or 1;
  • R 31 , R 32 and R 33 which may be identical or different, represent: a hydrogen atom
  • a monovalent hydrocarbon-based radical optionally comprising one or more hetero atoms chosen from a sulfur atom, an oxygen atom, a nitrogen atom, a phosphorus atom and a silicon atom, optionally substituted with one or more radicals chosen from:
  • an aromatic or heteroaromatic ring which is unsubstituted or substituted with one or more radicals chosen from a halogen atom, a hydroxyl radical, an alkoxy radical and a mono- or
  • a radical that increases the solubility of the phosphine in water such as sulfonate, sulfinate, phosphonate or carboxylate radicals, a substituted or unsubstituted, aromatic or non-aromatic
  • the substituents are chosen from halo, hydroxyl, alkyl, haloalkyl, alkoxy, amino, mono- or dialkylamino, mono- or
  • the radical p- methoxyphenyl is a substituted aryl radical.
  • the radicals R 31 , R 32 and R 33 do not simultaneously represent a hydrogen atom.
  • At least one of the radicals R 31 , R 32 and R 33 denotes, as a hydrocarbon-based radical, an optionally substituted alkyl radical.
  • R 31 , R 32 and R 33 are chosen from a hydrogen atom; an alkyl radical; a cycloalkyl radical optionally substituted with one or more alkyl radicals; an alkoxy radical; an alkoxyalkyl radical; a haloalkyl radical; a cyanoalkyl radical; a hydroxyalkyl radical; a
  • a pyridyl radical a trialkylsilyl radical
  • R 31 , R 32 and R 33 may be chosen from a hydrogen atom; a methyl radical; an ethyl radical; a propyl radical; an isopropyl radical; an n-butyl radical; an isobutyl radical; a tert-butyl radical; an octyl radical; a cyclohexyl radical; a cyclopentyl radical; a methoxy radical; an ethoxy radical; a methoxypropyl radical; a chloroethyl radical; a cyanoethyl
  • radical a hydroxymethyl radical; a hydroxypropyl radical; a carboxyethyl radical; a chlorine atom; a hydroxyl radical; a carboxyl radical; a trifluoromethyl radical; a chloromethyl radical; an allyl radical; a vinyl radical; a dimethylamino radical; a diethylamino radical; a di ( isopropyl ) amino radical; a phenyl radical; an o-tolyl radical; an m-tolyl radical; a p-tolyl radical; a dimethylphenyl radical; a trimethylphenyl radical; an o-methoxyphenyl radical; an m-methoxyphenyl radical; a p- methoxyphenyl radical; a dimethoxyphenyl radical; a
  • trimethoxyphenyl radical an o- (dimethylamino) phenyl radical; an m- (dimethylamino) phenyl radical; a p- (dimethylamino) phenyl
  • phosphines that are useful in the context of the invention may be optionally salified with strong mineral acids, for
  • HC1, HBr, H 2 S0 4 or HBF 4 organic acids, for instance acetic acid, lactic acid, tartaric acid, citric acid or succinic acid .
  • the phosphine(s) that is (are) useful in the context of the invention is (are) chosen from monophosphines.
  • q is then preferably equal to 1.
  • benzyldiphenylphosphine bis (3, 4, 5- trimethoxyphenyl ) chlorophosphine ; bis (3,4,5- trimethoxyphenyl ) phosphine;
  • butyldichlorophosphine butyldiphenylphosphine ; tert- butyldiphenylphosphine; cyclohexyl (diethylamino) chlorophosphine; cyclohexyl (dimethyl-amino) chlorophosphine;
  • cyclohexyldichlorophosphine cyclohexyldiphenylphosphine ; 2- chloroethyldiphenylphosphine; 2- (dicyclohexylphosphino) biphenyl ; 2-dicyclo-hexylphosphino-2 ' - (N, N-dimethylamino) biphenyl; diethyl- aminodiethylphosphine; dimethylaminodichlorophosphine ; (4- dimethylaminophenyl ) diphenylphosphine; N- [ (diphenyl- phosphinyl ) methyl ] -N-methylaniline; o-diphenylphosphinobenzoic acid; 2-methoxy (dichlorophosphino) benzene; 4- methoxyphenyl (diethylamino) chlorophosphine; 4- methoxyphenyl (dimethylamin
  • triphenylphosphine diallylphenylphosphine; dibenzylphosphine ; dibutylphenylphosphine; dibutylphosphine ;
  • dicyclohexylchlorophosphine dicyclohexylphenylphosphine ;
  • diethylphenylphosphine diethylphosphine ; diethylphosphine ; diisobutylphosphine; diisopropylchlorophosphine; diisopropylphosphine;
  • dimethyl (phenyl ) phosphine dimethyl ( trimethylsilyl) phosphine ; dimethylchlorophosphine; diphenyl (o-tolyl ) phosphine; diphenyl (p- tolyl) phosphine; diphenyl (trimethylsilyl) phosphine;
  • diphenylpropylphosphine diphenylvinylphosphine ; di-tert- butylchlorophosphine; di-tert-butylhydroxyphosphine ; di-tert- butylmethylphosphine ; di-tert-butylphenylphosphine ; di-tert- butylphosphine; divinylphenylphosphine ; ethy1-dichlorophosphine ; ethyldiphenylphosphine ; isopropyl-dichlorophosphine ; methoxydiethoxyphosphine ; methyl-dichlorophosphine ;
  • phenylphosphine propyldichlorophosphine ; tert- butylbis ( trimethylsilyl ) phosphine ; tert-butyldichlorophosphine ; tert-butyldiethylphosphine; tert-butyldiphenylphosphine; tert- butylphosphine ; tri(m-tolyl) phosphine; tri(o-tolyl) phosphine ; tri (p-tolyl) phosphine; tricyclohexylphosphine;
  • tricyclopentylphosphine triethylphosphine ; triisobutylphosphine ; triisopropylphosphine ; trimethylphosphine ; tri-n-butylphosphine ; tri-n-octylphosphine ; tripropylphosphine ; tris(l- naphthyl ) phosphine; tris ( 2 , 4 , 6-trimethylphenyl ) phosphine;
  • t is ( hydroxymethyl ) phosphine ; tris (trimethylsilyl ) phosphine ;
  • the monophosphines are chosen from:
  • the phosphine (s) that is (are) useful in the context of the invention is (are) diphosphines .
  • q is then ⁇ preferably equal to 2.
  • the linker L is a covalent bond or a divalent radical chosen from a binaphthylene radical; a methylene radical; an ethylene radical; a propylene radical; a butylene radical; a pentylene radical; a hexylene radical; a phenylene radical; a meta-dimethylenebenzene radical; an N- methyl-N ' -methylhydrazo radical; a vinylene radical; and a diethyleneoxy radical.
  • a binaphthylene radical a methylene radical; an ethylene radical; a propylene radical; a butylene radical; a pentylene radical; a hexylene radical; a phenylene radical; a meta-dimethylenebenzene radical; an N- methyl-N ' -methylhydrazo radical; a vinylene radical; and a diethyleneoxy radical.
  • diphosphines that are useful in the context of the invention, mention may be made of 2,2'- bis (dicyclohexylphosphino) -1,1' -binaphthyl ; 2,2'-bis[bis(3,5- dimethylphenylphosphino) ] -1, 1 ' -binaphthyl ; l,4-bis[bis(3,5- dimethylphenyl ) phosphino] butane; 1, 2-bis [bis (3, 5- dimethylphenyl ) phosphino] ethane; bis [bis (3, 5- dimethylphenyl ) phosphino] methane; l,5-bis[bis(3,5- dimethylphenyl ) phosphino] pentane; 1, 3-bis [bis (3, 5- dimethylphenyl ) phosphino] propane; 2,2'-bis[bis(3,5- ditrifluoromethylphenyl ) phosphino] propane
  • (2R, 3R) is (dicyclohexylphosphino) butane; (2S, 3S) - bis (dicyclohexylphosphino) butane; 1, 2- bis (dicyclohexylphosphino) ethane;
  • the phosphine(s) that is (are) useful in the context of the invention is (are) soluble in a cosmetically acceptable medium.
  • the phosphine(s) that is (are) useful in the context of the invention is (are) water-soluble.
  • water-soluble means any phosphine whose solubility in water is greater than 0.01 wt% at 20°C.
  • the phosphine is
  • sugars mention may be made of ribose, glucose, maltose, galactose, lactose, and xylose.
  • reductones mention may be made of ascorbic acid and erythorbic acid.
  • boron hydrides such as sodium borohydride, lithium hydride, and phosphorous hydride.
  • Precursors of hydrides and especially of boron hydrides such as diborane, tetraborane, pentaborane, decaborane and dodecaborane can be used.
  • Preferred non thiol-based reducing agents are chosen from
  • the alkaline metal hydroxide may be selected from the group consisting of lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide, and cesium hydroxide.
  • the alkaline metal hydroxide is selected from sodium hydroxide and potassium hydroxide.
  • the alkaline earth metal hydroxide may be selected from the group consisting of beryllium hydroxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide and barium hydroxide.
  • the alkaline earth metal hydroxide is selected from magnesium hydroxide and calcium hydroxide.
  • the amount of the reshaping or deforming agent (s) in the cosmetic composition according to the present invention is not limited.
  • the .amount of the reshaping or deforming agent (s) can be 0.1 wt% to 15 wt%, preferably 0.5 wt% to 10 wt%, relative to the total weight of the cosmetic composition.
  • the cosmetic composition according to the present invention may also comprise at least one additive chosen, for example, from solvents, higher alcohols, pH regulating agents, protein
  • hydrolyzates hydrolyzates , swelling and penetrating agents, conditioning agents other than silicones and alkoxysilanes, agents for
  • fragrances and preserving agents fragrances and preserving agents.
  • the solvent may be chosen from water, organic solvents, and mixtures thereof.
  • the amount of the solvent (s) is not limited but can be 10 wt% to 90 wt%, preferably 30 wt% to 70 wt%,
  • Organic solvents may be chosen, by way of non-limiting example, from alkanols, polyols, benzyl alcohol, and phenylethyl alcohol. According to one embodiment, the solvent is chosen from ethanol, n-propanol, glycerol, propyleneglycol and isopropanol.
  • higher alcohol here means an alcohol having a linear, branched, or cyclic, saturated or unsaturated, C 3 -C 4 o hydrocarbon group, preferably a C 8 -C 2 o hydrocarbon group.
  • hydrocarbon group may be a C 8 -C 40 alkyl, alkenyl or aralkyl group.
  • the higher alcohols preferably used for the present invention mention may be made of stearyl alcohol and cetearyl alcohol.
  • the amount of the higher alcohol (s) is not limited.
  • the amount of the higher alcohol (s) can be 0.1 wt% to 10 wt%, preferably 1 wt% to 5 wt%, relative to the total weight of the cosmetic
  • the pH regulating agents may be chosen, for instance, from alkaline agents, such as ammonia, ammonium hydroxide,
  • the amount of the pH regulating agent (s) is not limited. The amount of the pH
  • regulating agent ( s ) can be 0.5 wt% to 10 wt%, preferably 0.1 wt% to 8 wt%, relative to the total weight of the cosmetic
  • the pH of the cosmetic composition according to the present invention may range from 2 to 13, for example, from 4 to 12, and preferably from 7 to 12.
  • the cosmetic composition according to the present invention may also comprise at least one organic acid.
  • the organic acid may be chosen, for example, from acids comprising at least one organic acid.
  • ⁇ chosen from carboxylic, sulfonic, phosphonic, and phosphoric acid functional groups. They may further comprise other chemical functional groups, for instance, hydroxy and amino functional groups. They may be saturated or unsaturated.
  • organic acids include acetic acid, propanoic acid, butanoic acid, lactic acid, glycolic acid, ascorbic acid, maleic acid, phthalic acid, succinic acid, taurine, tartaric acid, gluconic acid, glucuronic acid, and citric acid.
  • the thickener may be chosen, for example, from cellulose-based thickeners such as hydroxyethylcellulose, hydroxypropylcellulose, and carboxymethylcellulose; guar gum and derivatives thereof, for example, hydroxypropyl guar, marketed by RHODIA under the
  • JAGUAR HP 105 and microbial gums such as xanthan gum and scleroglucan gum; and synthetic thickeners such as cetyl stearyl alcohol, acrylic and acrylamidopropane sulfonic acid crosslinked homopolymers , for example Carbomer, associative non ionic, anionic, cationic, and amphoteric polymers, such as
  • Suitable conditioning agents which may be used according to the present invention include, but are not limited to cationic
  • surfactants cationic polymers, ceramides, fatty esters, and mineral oils.
  • Preferred conditioning agents are cationic
  • surfactants such as behentrimonium chloride marketed by CLARIANT under the reference GENAMIN KDNP.
  • the cosmetic composition used according to the present invention may be in any form that can suitably be applied onto the hair, for example, lotions, serum type solutions, gels, water-in-oil emulsions, oil-in-water emulsions, and combinations thereof, with a more or less thick, liquid consistency, such as milks and creams that are more or less creamy, and foams.
  • the cosmetic composition used according to the present invention may be in a form chosen from lotions, solutions, gels, foams, and creams .
  • the cosmetic composition according to the present invention may be conditioned in different forms, for example, in tubes, in cosmetic jars, in sprays, in pump containers, and in aerosol containers, in order to distribute the cosmetic composition as a spray or as a foam.
  • the cosmetic composition according to the present invention may be contained in a two-compartment container.
  • the cosmetic composition according to the present invention is conditioned in an aerosol device, it comprises at least one propellant, which may be chosen from volatile hydrocarbons, such as n-butane, propane, isobutane, pentane, halogenated hydrocarbons, and mixtures thereof.
  • propellants include, but are not limited to, carbon dioxide, nitrous oxide, dimethyl ether (DME), nitrogen, and compressed air. Combinations of propellants may also be used. According to at least one embodiment, the propellant is dimethylether .
  • the propellant may be present in the cosmetic composition in an amount ranging from 5 to 90% by weight relative to the total weight of the cosmetic composition within the aerosol device, for example, from 10 to 60%.
  • the cosmetic composition of the present invention is preferably intended for permanently deforming or reshaping keratin fibers such as hair.
  • the composition ' according to the present invention comprising the at least one alkoxysilane, at least one silicone, and at least one reshaping or deforming agent selected from the group consisting of thiol-based. reducing agents, non thiol-based reducing agents, alkaline metal hydroxides and alkaline earth metal hydroxides can be applied onto the keratin fibers, and optionally rinsed off.
  • the composition ' according to the present invention comprising the at least one alkoxysilane, at least one silicone, and at least one reshaping or deforming agent selected from the group consisting of thiol-based. reducing agents, non thiol-based reducing agents, alkaline metal hydroxides and alkaline earth metal hydroxides can be applied onto the keratin fibers, and optionally rinsed off.
  • the composition ' according to the present invention comprising the at least one alkoxysilane, at least one silicone, and at least one reshaping or deforming agent selected from
  • composition of the present invention is then allowed to stand on the keratin fibers so as to let it penetrate into the keratin fibers, for example, for a time period of up to 30 minutes, such as from 5 to 15 minutes.
  • the keratin fibers may be rinsed with water after the composition is applied and allowed to react for a while.
  • the keratin fibers are provided with mechanical tension and/or heat, for deforming or reshaping the keratin fibers.
  • the keratin fibers may then be set in form, for example, by means of a brush and/or an iron.
  • the keratin fibers are oxidized with an oxidizing composition.
  • the oxidizing composition comprises at least one oxidizing agent.
  • the oxidizing agent (s) is (are) chosen from hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides , and peroxygenated salts, for instance alkali metal or alkaline-earth metal persulfates, perborates and percarbonates , and peracids and precursors thereof.
  • the oxidizing agent is advantageously constituted by hydrogen peroxide, especially as an aqueous solution (aqueous hydrogen peroxide solution) , the concentration of which may range from 1 to 50 wt% and preferably from 5 to 40 wt% .
  • the oxidizing composition may be aqueous or nonaqueous.
  • aqueous means that the developer comprises more than 5% by weight of water, preferably more than 10% by weight of water and even more advantageously more than 20% by weight of water.
  • the pH. of the oxidizing composition when it is aqueous, is less than 7.
  • the oxidizing composition may also contain other ingredients conventionally used in the field, especially those detailed previously in the context of the cosmetic composition according to the present invention.
  • the oxidizing composition may be in various forms, for instance a solution, an emulsion or a gel.
  • the keratin fibers may be rinsed with water after the oxidizing composition is applied and allowed to react for a while.
  • first, keratin fibers are subjected to mechanical tension for deformation.
  • the mechanical tension can be applied to the keratin fibers by any means to deform the keratin fibers to an intended shape.
  • the mechanical tension may be provided by at least one reshaping means selected from the group consisting of a curler, a roller, a plate and an iron.
  • the reshaping means may comprise at least one heater.
  • the cosmetic composition according to the present invention is applied to the keratin fibers.
  • a disulfide bond in the keratin fibers is broken.
  • composition may be performed by any means, such as a brush and a comb.
  • the keratin fibers to which the mechanical tension has been applied should be treated with the cosmetic composition.
  • an oxidizing composition comprising one or several oxidizing agents as described above is applied onto the keratin fibers to form a disulfide bond again.
  • keratin fibers such as hair can be reshaped.
  • the keratin fibers may be rinsed after the step of applying the cosmetic composition according to the present invention onto the keratin fibers and/or after the step of oxidizing the keratin fibers .
  • the cosmetic composition according to the present invention may be in the form of a kit.
  • the kit may be for deforming keratin fibers, comprising:
  • first composition comprising at least one al koxysilane ; and a second composition comprising at least one silicone,
  • either the first composition and/or second composition comprise at least one reshaping or deforming agent selected from the group consisting of thiol-based reducing agents, non thiol-based
  • the kit comprises a third composition comprising at least one oxidizing agent.
  • a third composition comprising at least one oxidizing agent.
  • compositions were prepared (the unit of the content is grams based on material as provided) .
  • Composition 1 (Reducing Cream)
  • Composition 2 (Oxidizing Lotion)
  • Composition 1 was applied onto a swatch of natural hair (2.7g) in a weight ratio of 1:2 of the swatch to Composition 1, and left for 15 minutes. After a pause, the swatch was rinsed, squeezed, and dried. The swatch was treated twice with an iron (180°C) to be straightened.
  • Composition 2 was applied onto the swatch in a weight ratio of 1:2 of the swatch to Composition 2, and left for 5 minutes. After a pause, the swatch was rinsed and dried.
  • the swatch which had been treated as above was completely straightened.
  • the swatch showed very good cosmetic properties in terms ' of softness and suppleness, and the cosmetic properties were able to be maintained even after 5 shampoos.
  • Comparative Example 1 The following composition was prepared (the unit of the content is grams based on material as provided) .
  • Composition 3 (Reducing Cream)
  • Composition 3 was applied onto a swatch of natural hair (2.7g) in a weight ratio of 1:2 of the swatch to Composition 3, and left for 15 minutes. After a pause, the swatch was rinsed, squeezed, and dried. The swatch was treated twice with an iron (180°C) to be straightened.
  • Composition 2 was applied onto the swatch in a weight ratio of 1:2 of the swatch to Composition 2, and left for 5 minutes. After a pause, the swatch was rinsed and dried.
  • Composition 1 The feel to the touch was brittle and dry.
  • composition 4 (Reducing Cream)
  • Composition 4 was applied onto a swatch of natural hair (2.7g) in a weight ratio of 1:2 of the swatch to Composition 4, and left for 15 minutes. After a pause, the swatch was rinsed, squeezed, and dried. The swatch was treated twice with an iron (180°C) to be straightened.
  • Composition 2 was applied onto the swatch in a weight ratio of 1:2 of the swatch to Composition 2, and left for 5 minutes. After a pause, the swatch was rinsed and dried.
  • the swatch showed very good cosmetic properties in terms of softness and suppleness, and the cosmetic properties were able to be maintained even after 5 shampoos.
  • composition 5 (Reducing Cream)
  • Composition 5 was applied onto a swatch of natural hair (2.7g) in a weight ratio of 1:2 of the swatch to Composition 5, and left for 15 minutes. After a pause, the swatch was rinsed, squeezed, and dried. The swatch was treated twice with an iron (180°C) to be straightened.
  • Composition 2 was applied onto the swatch in a weight ratio of 1:2 of the swatch to Composition 2, and left for 5 minutes. After a pause, the swatch was rinsed and dried.
  • the swatch which had been treated as above was straightened.
  • the swatch had softness and suppleness just after the above
  • composition 6 (Reducing Lotion)
  • Composition 8 (Oxidizing Lotion)
  • Compositions 6 and 7 were mixed in a weight ratio of 4:1 of Composition 6 to Composition 7. The obtained mixture was applied onto a swatch, (lg) of natural Japanese hair which had been already wound onto a curler with a diameter of 1.4 cm. After being left for 15 minutes, the swatch was rinsed. Then,
  • Composition 8 was applied onto the swatch, and left for 10 minutes. After a pause, the swatch was rinsed, unwound and dried at ambient temperature.
  • the hair which had been treated as above showed very good curl, and exhibited excellent cosmetic properties in terms of softness and disentanglement. These cosmetic properties were able to be maintained even after several shampoos.
  • Comparative Example 3 The following compositions were prepared (the unit of the content is grams based on material as provided) .
  • Composition 9 (Reducing Lotion)
  • Compositions 9 and 10 were mixed in a weight ratio of 4:1 of Composition 9 to Composition 10. The obtained mixture was applied onto a swatch (lg) of natural Japanese hair which had been already wound onto a curler with a diameter of 1.4 cm.
  • composition 8 was applied onto the swatch, and left for 10 minutes. After a pause, the swatch was rinsed, unwound and dried in ambient temperature.
  • the hair which had been treated as above showed the same curl as seen in Example 3.
  • the cosmetic properties of the hairof Comparative Example 3 just after the above treatment and after several shampoos were inferior to those of the hair in Example 3 in terms of softness and disentanglement.
  • composition 11 (Reducing Cream)
  • Composition 12 (Oxidizing Lotion)
  • Composition 11 is applied onto a swatch of natural hair (2.7g) in a weight ratio of 1:2 of the swatch to Composition 11, and the swatch is left for 15 minutes. After a pause, the swatch is rinsed, squeezed, and dried. The swatch is treated twice with an iron (180°C) to be straightened.
  • Composition 12 is applied onto the swatch in a weight ratio of 1:2 of the swatch to Composition 12, and the swatch is left for 5 minutes. After a pause, the swatch is rinsed and dried.
  • the swatch treated as above is completely straightened.
  • the swatch shows very good cosmetic properties in terms of softness and suppleness, and the cosmetic properties are able to be maintained even after 5 shampoos.
  • Comparative Example 4 The following composition is prepared (the unit of the content is grams based on material as provided) .
  • Composition 13 (Reducing Cream)
  • Composition 13 is applied onto a swatch of natural hair (2.7g) in a weight ratio of 1:2 of the swatch to Composition 13, and the swatch is left for 15 minutes. After a pause, the swatch is rinsed, squeezed, and dried. The swatch is treated twice with an iron (180°C) to be straightened.
  • Composition 12 is applied onto the swatch in a weight ratio of 1:2 of the swatch to Composition 12, and the swatch is left for 5 minutes. After a pause, the swatch is rinsed and dried.
  • the swatch treated as above is straightened. However, the cosmetic properties of the swatch are inferior to those of the swatch treated with Composition 11.. The feel to the touch is brittle and dry.
  • composition 14 (Reducing Cream)
  • Composition 14 is applied onto a swatch of natural hair (2.7g) in a weight ratio of 1:2 of the swatch to Composition 14, and the swatch is left for 15 minutes. After a pause, the swatch is rinsed, squeezed, and dried. The swatch is treated twice with an iron (180°C) to be straightened.
  • Composition 12 is applied onto the swatch in a weight ratio of 1:2 of the swatch to Composition 12, and the swatch is left for 5 minutes. After a pause, the swatch is rinsed and dried.
  • the swatch treated as above is completely straightened.
  • the swatch shows very good cosmetic properties in terms of softness and suppleness, and the cosmetic properties are able to be maintained even after 5 shampoos.
  • composition 15 (Reducing Cream)
  • Composition 15 is applied onto a swatch of natural hair (2.7g) in a weight ratio of 1:2 of the swatch to Composition 15, and the swatch is left for 15 minutes. After a pause, the swatch is rinsed, squeezed, and dried. The swatch is treated twice with an iron (180°C) to be straightened.
  • Composition 12 is applied onto the swatch in a weight ratio of 1:2 of the swatch to Composition 12, and the swatch is left for 5 minutes. After a pause, the swatch is rinsed and dried.
  • the swatch treated as above is straightened.
  • the swatch has softness and suppleness just after the above treatment. However, these cosmetic properties disappear after the first shampoo.
  • composition 16 (Reducing Lotion)
  • Composition 18 (Oxidizing Lotion)
  • Compositions 16 and 17 are mixed in a weight ratio of 4:1 of Composition 16 to Composition 17. The obtained mixture is applied onto a swatch (lg) of natural Japanese hair which has been already wound onto a curler with a diameter of 1.4 cm.
  • the swatch After being left for 15 minutes, the swatch is rinsed. Then, Composition 18 is applied onto the swatch, and the swatch is left for 10 minutes. After a pause, the swatch is rinsed, unwound and dried at ambient temperature.
  • the hair treated as above shows very good curl, and exhibited excellent cosmetic properties in terms of softness and
  • Comparative Example 6 The following compositions are prepared (the unit of the content is grams based on material as provided) .
  • Composition 19 (Reducing Lotion)
  • Compositions 19 and 20 are mixed in a weight ratio of 4:1 of Composition 19 to Composition 20.
  • the obtained mixture is applied onto a swatch (lg) of natural Japanese hair which has already been wound onto a curler with a diameter of 1.4 cm.
  • the swatch After being left for 15 minutes, the swatch is rinsed. Then, Composition 18 is applied onto the swatch, and the swatch is left for 10 minutes. After a pause, the swatch is rinsed, unwound and dried at ambient temperature.
  • the hair treated as above shows the same curl as seen in Example 6.
  • the cosmetic properties of the hair of Comparative Example 6 just after the above treatment and after several shampoos in terms of softness and disentanglement are inferior to those of the hair in Example 6.
  • composition 21 The following composition was prepared (the unit of the content is grams based on material as provided) .
  • Composition 21 was applied onto a swatch of naturally curly hair (0.2g) in a weight ratio of 1:2 of the swatch to Composition 21, and left for 10 minutes. After a pause, the swatch was rinsed with water and dried.
  • the swatch showed very good cosmetic properties in terms of softness and suppleness, and the cosmetic properties were able to be maintained even after 5 shampoos.
  • composition was prepared (the unit of the content is grams based on material as provided) .
  • Composition 22 was applied onto a swatch of naturally curly hair (0.2g) in a weight ratio of 1:2 of the swatch to Composition 22, and left for 10 minutes. After a pause, the swatch was rinsed with water and dried. The swatch which had been treated as above was completely straightened. However, the cosmetic properties of the swatch were inferior to those of the swatch which had been treated with Composition 21.

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Abstract

La présente invention concerne une composition cosmétique pour les fibres de kératine, qui comprend : (a) au moins un alcoxysilane ; (b) au moins une silicone ; et (c) au moins un élément choisi dans le groupe constitué par des agents de réduction à base de thiol, des agents de réduction non à base de thiol, des hydroxydes de métaux alcalins et des hydroxydes de métaux alcalino-terreux. La présente invention est utile étant donné qu'elle peut entraîner une réduction des lésions aux fibres de kératine dues à la restructuration ou à la déformation permanentes des fibres de kératine, et qu'elle peut conférer aux fibres de kératines de bonnes propriétés cosmétiques telles qu'une apparence douce ou souple et une sensation au toucher qui peut durer longtemps même après un shampooing, tout en conférant aux fibres de kératine de bons effets de restructuration ou de déformation permanentes.
PCT/JP2011/050590 2010-01-19 2011-01-07 Composition cosmétique pour les fibres de kératine WO2011089985A1 (fr)

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US31703310P 2010-03-24 2010-03-24
US31703810P 2010-03-24 2010-03-24
US31702610P 2010-03-24 2010-03-24
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8343238B1 (en) 2011-12-30 2013-01-01 L'oreal Sa. Process for altering the appearance of hair using a composition containing dyes and non-hydroxide bases
US8591872B2 (en) 2011-12-30 2013-11-26 L'oreal Composition and process for reducing the curl and frizziness of hair
WO2014072657A1 (fr) * 2012-11-09 2014-05-15 L'oreal Composition comprenant un derive dicarbonyle et procede de lissage des cheveux a partir de cette composition
WO2013098335A3 (fr) * 2011-12-30 2015-01-22 L'oreal Procédé de modification de l'apparence de cheveux utilisant une composition contenant des colorants et des bases non-hydroxydes
WO2013098332A3 (fr) * 2011-12-30 2015-01-22 L'oreal Composition et procédé de réduction des boucles et des frisotis de cheveux
EP2857004A1 (fr) * 2013-10-07 2015-04-08 The Procter and Gamble Company Procédé de défrisage des cheveux impliquant des sucres réducteurs
EP2866773B1 (fr) 2012-06-29 2017-08-09 Henkel AG & Co. KGaA Procede de lissage chimique de cheveux humains ii
WO2017192990A1 (fr) 2016-05-05 2017-11-09 Avlon Industries, Inc. Compositions et procédé de relaxation capillaire
US10434051B2 (en) 2014-12-19 2019-10-08 The Procter And Gamble Company Shaping keratin fibers using arabinose and ethylene carbonate
US10568826B2 (en) 2014-12-19 2020-02-25 The Procter And Gamble Company Shaping keratin fibres using a pretreatment and a protein crosslinking composition
US10912726B2 (en) 2013-12-19 2021-02-09 The Procter And Gamble Company Shaping keratin fibres using a reducing composition and a fixing composition
US10945931B2 (en) 2015-06-18 2021-03-16 The Procter And Gamble Company Shaping keratin fibres using dialdehyde compounds
US11096879B2 (en) 2013-12-19 2021-08-24 The Procter And Gamble Plaza Shaping keratin fibres using an active agent comprising a functional group selected from the group consisting of: -C(=O)-, -C(=O)-H, and -C(=O)-O-
US11103434B2 (en) 2013-12-19 2021-08-31 The Procter And Gamble Company Shaping keratin fibres using carbonate ester
US11110046B2 (en) 2013-12-19 2021-09-07 The Procter And Gamble Company Shaping keratin fibres using 2-hydroxypropane-1,2,3-tricarboxylic acid and/or 1,2,3,4-butanetetracarboxylic acid
US11129784B2 (en) 2013-12-19 2021-09-28 The Procter And Gamble Company Shaping keratin fibres using oxoethanoic acid and/or derivatives thereof
US11154480B2 (en) 2013-12-19 2021-10-26 The Procter And Gamble Company Shaping keratin fibres using a sugar

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Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8343238B1 (en) 2011-12-30 2013-01-01 L'oreal Sa. Process for altering the appearance of hair using a composition containing dyes and non-hydroxide bases
US8591872B2 (en) 2011-12-30 2013-11-26 L'oreal Composition and process for reducing the curl and frizziness of hair
WO2013098335A3 (fr) * 2011-12-30 2015-01-22 L'oreal Procédé de modification de l'apparence de cheveux utilisant une composition contenant des colorants et des bases non-hydroxydes
WO2013098332A3 (fr) * 2011-12-30 2015-01-22 L'oreal Composition et procédé de réduction des boucles et des frisotis de cheveux
EP2866773B1 (fr) 2012-06-29 2017-08-09 Henkel AG & Co. KGaA Procede de lissage chimique de cheveux humains ii
WO2014072657A1 (fr) * 2012-11-09 2014-05-15 L'oreal Composition comprenant un derive dicarbonyle et procede de lissage des cheveux a partir de cette composition
FR2997849A1 (fr) * 2012-11-09 2014-05-16 Oreal Composition comprenant un derive dicarbonyle et procede de lissage des cheveux a partir de cette composition
EP2857004A1 (fr) * 2013-10-07 2015-04-08 The Procter and Gamble Company Procédé de défrisage des cheveux impliquant des sucres réducteurs
WO2015054018A1 (fr) * 2013-10-07 2015-04-16 The Procter & Gamble Company Procédé de lissage de cheveux impliquant des sucres réducteurs
US9415000B2 (en) 2013-10-07 2016-08-16 The Procter & Gamble Company Hair straightening method involving reducing sugars
US10912726B2 (en) 2013-12-19 2021-02-09 The Procter And Gamble Company Shaping keratin fibres using a reducing composition and a fixing composition
US11096879B2 (en) 2013-12-19 2021-08-24 The Procter And Gamble Plaza Shaping keratin fibres using an active agent comprising a functional group selected from the group consisting of: -C(=O)-, -C(=O)-H, and -C(=O)-O-
US11103434B2 (en) 2013-12-19 2021-08-31 The Procter And Gamble Company Shaping keratin fibres using carbonate ester
US11110046B2 (en) 2013-12-19 2021-09-07 The Procter And Gamble Company Shaping keratin fibres using 2-hydroxypropane-1,2,3-tricarboxylic acid and/or 1,2,3,4-butanetetracarboxylic acid
US11129784B2 (en) 2013-12-19 2021-09-28 The Procter And Gamble Company Shaping keratin fibres using oxoethanoic acid and/or derivatives thereof
US11154480B2 (en) 2013-12-19 2021-10-26 The Procter And Gamble Company Shaping keratin fibres using a sugar
US10434051B2 (en) 2014-12-19 2019-10-08 The Procter And Gamble Company Shaping keratin fibers using arabinose and ethylene carbonate
US10568826B2 (en) 2014-12-19 2020-02-25 The Procter And Gamble Company Shaping keratin fibres using a pretreatment and a protein crosslinking composition
US10945931B2 (en) 2015-06-18 2021-03-16 The Procter And Gamble Company Shaping keratin fibres using dialdehyde compounds
EP3452174A4 (fr) * 2016-05-05 2020-01-01 Avlon Industries, Inc. Compositions et procédé de relaxation capillaire
US10568829B2 (en) 2016-05-05 2020-02-25 Avlon Industries, Inc. Hair relaxer compositions and method
WO2017192990A1 (fr) 2016-05-05 2017-11-09 Avlon Industries, Inc. Compositions et procédé de relaxation capillaire

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