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WO2025018430A1 - Composition convenant aux fibres de kératine - Google Patents

Composition convenant aux fibres de kératine Download PDF

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Publication number
WO2025018430A1
WO2025018430A1 PCT/JP2024/080108 JP2024080108W WO2025018430A1 WO 2025018430 A1 WO2025018430 A1 WO 2025018430A1 JP 2024080108 W JP2024080108 W JP 2024080108W WO 2025018430 A1 WO2025018430 A1 WO 2025018430A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
composition
less
keratin fibers
composition according
Prior art date
Application number
PCT/JP2024/080108
Other languages
English (en)
Inventor
Yoshiki Shibuya
Original Assignee
L'oreal
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP2023118447A external-priority patent/JP2025015195A/ja
Priority claimed from FR2308992A external-priority patent/FR3152387A3/fr
Application filed by L'oreal filed Critical L'oreal
Publication of WO2025018430A1 publication Critical patent/WO2025018430A1/fr

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Classifications

    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring

Definitions

  • the present invention mainly relates to a composition which is suitable for reshaping, preferably straightening, keratin fibers such as hair.
  • Straightening keratin fibers such as hair by heating the keratin fibers with an iron is popular for making unruly keratin fibers manageable and making keratin fibers have less volume and look more desirable.
  • Such a straightening method using a heating iron is convenient for quick styling, but the style lasts only a short period of time, e.g., until the next shampooing.
  • a long-lasting straightening method is required for many consumers.
  • WO 2014/131469 discloses a process for straightening keratin fibers by heating with an iron, without using reducing and oxidizing agents, wherein glyoxylic acid is used to straighten the keratin fibers.
  • US-A-2023/742 discloses a semi-permanent hair straightening composition including 15% to 20% by weight of glyoxylic acid and 0.1% to 5% by weight of levulinic acid.
  • An objective of the present invention is to provide a composition which is useful for reshaping keratin fibers such as hair, based on treating the keratin fibers with glyoxylic acid or a derivative thereof, which can provide the keratin fibers with longer-lasting reshaping effects.
  • composition for keratin fibers, such as hair comprising:
  • the amount of the (a) compound(s) in the composition according to the present invention may be less than 15% by weight, preferably less than 14% by weight, and more preferably less than 13% by weight, relative to the total weight of the composition.
  • the (b) compound may be selected from levulinic acid, a salt thereof, and a mixture thereof.
  • the amount of the (b) compound(s) in the composition according to the present invention may be 10% by weight or less, preferably 8% by weight or less, and more preferably 6% by weight or less, relative to the total weight of the composition.
  • the (c) aminosilicone may be selected from the group consisting of amodimethicone, aminopropyldimethicone, and a mixture thereof.
  • the amount of the (c) amino silicone(s) in the composition according to the present invention may be from 0.01% to 10% by weight, preferably from 0.05% to 5% by weight, and more preferably from 0.1% to 1% by weight, relative to the total weight of the composition.
  • composition according to the present invention may further comprise (d) water.
  • composition according to the present invention may further comprise (e) at least one betaine compound.
  • composition according to the present invention may further comprise (f) at least one fatty amine.
  • the pH of the composition according to the present invention may be 7 or less, preferably 6 or less, and more preferably 5 or less.
  • composition according to the present invention may not comprise any ammonia or thiol compound, or may comprise less than 1% by weight, preferably less than 0.5% by weight, and more preferably less than 0.1% by weight of ammonia or thiol compound, relative to the total weight of the composition.
  • composition according to the present invention may not comprise any reducing agent or oxidizing agent, or may comprise less than 1% by weight, preferably less than 0.5% by weight, and more preferably less than 0.1% by weight of a reducing agent or an oxidizing agent, relative to the total weight of the composition.
  • composition according to the present invention may be intended for reshaping, preferably straightening, keratin fibers, such as hair.
  • the present invention also relates to a process for reshaping, preferably straightening, keratin fibers such as hair, comprising the steps of:
  • the present invention also relates to a kit for reshaping, preferably straightening, keratin fibers such as hair, comprising: at least one selected from the group consisting of an iron, a curler, a comb, a dryer, and a combination thereof, preferably at least one heating iron, heating curler, heating comb or heating dryer which is capable of providing the keratin fibers with a temperature of more than 50°C, preferably more than 100°C, and more preferably more than 150°C; and the composition according to the present invention.
  • compositions which is useful for reshaping keratin fibers such as hair, based on treating the keratin fibers with glyoxylic acid or a derivative thereof, and which can provide the keratin fibers with longer-lasting reshaping effects.
  • the present invention mainly relates to a composition for keratin fibers, such as hair, comprising:
  • the present invention can improve reshaping keratin fibers such as hair, based on treating the keratin fibers with glyoxylic acid or a derivative thereof, by providing longer-lasting reshaping effects.
  • the present invention can provide keratin fibers such as hair with longer-lasting reshaping effects.
  • the present invention can lengthen or prolong the reshaping effects for keratin fibers provided by using a composition including only glyoxylic acid or a derivative thereof.
  • the present invention can further maintain the straightened or curled shape of keratin fibers, or can prevent or reduce loss of the straightened or curled shape of keratin fibers over time.
  • the present invention can provide better prevention for the keratin fibers returning to the original wavy shape, after straightening the keratin fibers, in particular after shampooing.
  • the present invention can also provide keratin fibers with sufficient immediate reshaping effects.
  • the keratin fibers treated with the present invention to be straight can have less volume or less frizz due to the reduction of curls of the keratin fibers.
  • the reshaping effects provided by the present invention can last a long time, for example, even after shampooing the keratin fibers.
  • the present invention can also provide the shape of keratin fibers with good resistance to shampooing.
  • the present invention can provide keratin fibers with less damage as compared to conventional permanent reshaping processes, because the present invention does not need to use any reducing/oxidizing agents. Therefore, it can be easy to comb the keratin fibers treated by the present invention. Thus, the keratin fibers treated with the present invention can be easy to manage. Also, the keratin fibers treated by the present invention can be stronger than those treated by conventional permanent reshaping processes.
  • the present invention can use no or very little ammonia or thiol compound, and therefore, odor during the use of the present invention can be reduced as compared to the conventional processes which require the use of ammonia or a thiol compound. Also, the present invention can have good usability, for example, short processing time.
  • composition according to the present invention comprises:
  • the composition according to the present invention be a cosmetic composition, more preferably a cosmetic composition for reshaping keratin fibers, and even more preferably a cosmetic composition for one-step reshaping of keratin fibers. It is particularly preferable that the keratin fibers be hair.
  • composition according to the present invention comprises (a) at least one compound selected from the group consisting of glyoxylic acid, glyoxylic acid solvates, glyoxylic acid salts, glyoxylic acid esters, glyoxylic acid amides, and mixtures thereof.
  • a single type of (a) compound may be used, or two or more different types of (a) compounds may be used in combination.
  • the (a) compound is selected from the group consisting of glyoxylic acid, glyoxylic acid solvates, glyoxylic acid salts, glyoxylic acid esters, glyoxylic acid amides, and mixtures thereof.
  • the (a) compound is selected from glyoxylic acid and derivatives thereof.
  • glyoxylic acid solvates mention may be made of, for example, glyoxylic acid hydrates such as glyoxylic acid monohydrate.
  • glyoxylic acid salts mention may be made of, for example, alkaline metal salts or alkaline earth metal salts of glyoxylic acid such as sodium or potassium glyoxylate, and magnesium or calcium glyoxylate.
  • glyoxylic acid esters mention may be made of, for example, alkyl esters of glyoxylic acid such as methyl glyoxylate and ethyl glyoxylate.
  • glyoxylic acid amides mention may be made of, for example, N-glyoxyloylcarbocysteine and N-glyoxyloyl keratin amino acids.
  • glyoxylic acid it is preferable to use glyoxylic acid as the (a) compound.
  • the amount of the (a) compound(s) in the composition according to the present invention may be 0.1% by weight or more, preferably 0.5% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition.
  • the amount of the (a) compound(s) in the composition according to the present invention may be less than 15% by weight, preferably less than 14% by weight, and more preferably less than 13% by weight, relative to the total weight of the composition.
  • the amount of the (a) compound(s) in the composition according to the present invention may be from 0.1% to less than 15% by weight, preferably from 0.5% to less than 14% by weight, and more preferably from 1% to less than 13% by weight, relative to the total weight of the composition.
  • the amount of the (a) compound(s) in the composition according to the present invention may be 12% by weight or less, preferably 11% by weight or less, and more preferably 10% by weight or less, relative to the total weight of the composition.
  • the amount of the (a) compound(s) in the composition according to the present invention may be from 0.1% to 12% by weight, preferably from 0.5% to 11% by weight, and more preferably from 1% to 10% by weight, relative to the total weight of the composition.
  • composition according to the present invention comprises (b) at least one compound, different from the (a) compound, selected from keto acids, salts thereof, and mixtures thereof.
  • Two or more (b) compounds may be used in combination.
  • a single type of (b) compound or a combination of different types of (b) compounds may be used.
  • the keto acids may be selected from a-keto acids, P-keto acids, y-keto acids, and mixtures thereof.
  • a-keto acids may be compounds represented by the general formula (I): wherein
  • R 1 denotes a linear or branched Ci-Ce alkyl group, optionally substituted with an OH, COOH or a halogen atom such as a chlorine or bromine atom.
  • keto acid examples include pyruvic acid.
  • R 2 denotes a linear or branched Ci-Cg alkyl group, optionally substituted with an OH, COOH or a halogen atom such as a chlorine or bromine atom;
  • R 3 denotes a methylene group, optionally substituted with a halogen atom such as a chlorine or bromine atom.
  • p-keto acid examples include acetoacetic acid.
  • the y-keto acids may be represented by the general formula (III): wherein
  • R 2 denotes a linear or branched Ci-Ce alkyl group, optionally substituted with an OH, COOH or a halogen atom such as a chlorine or bromine atom;
  • R 4 denotes an ethylene group, optionally substituted with a halogen atom such as a chlorine or bromine atom.
  • y-keto acids include levulinic acid.
  • the salts of keto acid may be alkaline metal salts or alkaline earth metal salts of keto acid such as sodium or potassium salts of keto acid, and magnesium or calcium salts of keto acid.
  • (b) compound(s) y-keto acid, and more preferably levulinic acid and/or a salt thereof such as sodium levulinate.
  • the amount of the (b) compound(s) in the composition according to the present invention may be 0.1% by weight or more, preferably 0.5% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition.
  • the amount of the (b) compound(s) in the composition according to the present invention may be 10% by weight or less, preferably 8% by weight or less, and more preferably 6% by weight or less, relative to the total weight of the composition.
  • the amount of the (b) compound(s) in the composition according to the present invention may be from 0.1% to 10% by weight, preferably from 0.5% to 8% by weight, and more preferably from 1% to 6% by weight, relative to the total weight of the composition.
  • the amount of the (b) compound(s) in the composition according to the present invention may be 5% by weight or less, preferably 4% by weight or less, and more preferably 3% by weight or less, relative to the total weight of the composition.
  • the amount of the (b) compound(s) in the composition according to the present invention may be from 0.1% to 5% by weight, preferably from 0.5% to 4% by weight, and more preferably from 1% to 3% by weight, relative to the total weight of the composition.
  • the (b) compound(s) may be present in a lesser amount than the (a) compound(s) in the composition according to the present invention.
  • the weight ratio of the amount of the (a) compound(s) to the amount of the (b) compound(s) included in the composition according to the present invention may range from 1 : 1 to 15: 1, preferably from 1 : 1 to 10:1, and more preferably from 1:1 to 4 : 1.
  • composition according to the present invention comprises (c) at least one amino silicone.
  • Two or more aminosilicones may be used in combination.
  • a single type of aminosilicone or a combination of different types of aminosilicones may be used.
  • any aminosilicone compound in the field of cosmetics may be used.
  • aminosilicone here means a silicone comprising at least one primary, secondary or tertiary amine group or at least one quaternary ammonium group.
  • G independently designates a hydrogen atom, or a phenyl, OH, or a Ci-Cs alkyl group, for example methyl, or a Ci-Cg alkoxy group, for example methoxy, a and a' independently denote the number 0 or an integer from 1 to 3, in particular 0; b denotes 0 or 1 , and in particular 1 ; m and n are numbers such that the sum (n + m) ranges from 1 to 2,000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to 1,999 and in particular from 49 to 149, and for m to denote a number from 1 to 2,000 and in particular from 1 to 10;
  • R' independently denotes a monovalent group having the formula -CqHaqL in which q is a number ranging from 2 to 8 and L is an optionally quatemized amino group chosen from the following groups:
  • R" independently denotes hydrogen, phenyl, benzyl, or a saturated monovalent hydrocarbon-based group, for example a Ci-C 2 o alkyl group;
  • Q denotes a linear or branched C r H 2r group, r being an integer ranging from 2 to 6, preferably from 2 to 4;
  • A’ represents a cosmetically acceptable ion, in particular a halide such as fluoride, chloride, bromide or iodide.
  • a group of aminosilicones corresponding to this definition (B) is represented by the silicones called "trimethylsilylamodimethicone” having formula (C): in which n and m have the meanings given above, in formula B.
  • the weightaverage molecular weight (Mw) of the aminosilicone (C) may range from 100,000 to 2,500,000, preferably from 300,000 to 2,000,000, and more preferably from 500,000 to 1,500,000.
  • Ri, R2, and R3 independently represent a hydroxy or a C1-C4 alkoxy group, wherein at least one of the groups Ri to R3 denotes an alkoxy group.
  • the alkoxy group is preferably a methoxy group.
  • the hydroxy/alkoxy mole ratio ranges preferably from 0.2: 1 to 0.4: 1 and preferably from 0.25:1 to 0.35: 1 and more particularly equals 0.3:1.
  • the weight-average molecular weight (Mw) of the aminosilicone (D) ranges preferably from 2,000 to 1,000,000, more particularly from 3,500 to 200,000.
  • p and q are numbers such that the sum (p + q) ranges from 1 to 1,000, particularly from 50 to 350, and more particularly from 150 to 250; it being possible for p to denote a number from 0 to 999 and in particular from 49 to 349, and more particularly from 159 to 239 and for q to denote a number from 1 to 1,000, in particular from 1 to 10, and more particularly from 1 to 5;
  • Ri and R2 independently represent a hydroxy or C1-C4 alkoxy group, where at least one of the groups Ri or R2 denotes an alkoxy group.
  • the alkoxy group is preferably a methoxy group.
  • the hydroxy/alkoxy mole ratio ranges generally from 1 :0.8 to 1: 1.1 and preferably from 1:0.9 to 1: 1 and more particularly equals 1:0.95.
  • the weight-average molecular weight (Mw) of the aminosilicone (E) ranges preferably from 2,000 to 200,000, even more particularly from 5,000 to 100,000 and more particularly from 10,000 to 50,000.
  • silicones having structure (D) or (E) may include in their composition one or more other aminosilicones whose structure is different from formula (D) or (E).
  • a product containing an aminosilicone having structure (D) is sold by Wacker under the name BELSILADM 652.
  • a product containing an aminosilicone having structure (E) is sold by Wacker under the name FLUID WR 1300®.
  • Another group of amino silicones corresponding to this definition is represented by the following formula (F): in which: m and n are numbers such that the sum (n + m) ranges from 1 to 2,000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to 1,999 and in particular from 49 to 149, and for m to denote a number from 1 to 2,000 and in particular from 1 to 10;
  • A denotes a linear or branched alkylene group containing from 4 to 8 carbon atoms and preferably 4 carbon atoms. This group is preferably linear.
  • the weight-average molecular weight (Mw) of the aminosilicone (F) ranges preferably from 2,000 to 1,000,000 and even more particularly from 3,500 to 200,000.
  • a preferred silicone of formula (F) is amodimethicone sold under the tradename XIAMETER® MEM-8299 Cationic Emulsion by Dow.
  • G Another group of aminosilicones corresponding to this definition is represented by the following formula (G): in which: m and n are numbers such that the sum (n + m) ranges from 1 to 2,000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to 1,999 and in particular from 49 to 149, and for m to denote a number from 1 to 2,000 and in particular from 1 to 10;
  • A denotes a linear or branched alkylene group containing from 4 to 8 carbon atoms and preferably 4 carbon atoms. This group is preferably branched.
  • the weight-average molecular weight (Mw) of the aminosilicone (G) ranges preferably from 500 to 1,000,000 and even more particularly from 1,000 to 200,000.
  • a silicone having this formula is for example DOWSILTM2-8566 Amino Fluid by Dow.
  • Rs independently represents a monovalent hydrocarbon-based group containing from 1 to 18 carbon atoms, and in particular a Ci-Cis alkyl or C2-C18 alkenyl group, for example methyl;
  • Rs represents a divalent hydrocarbon-based group, in particular a Ci-Cis alkylene group or a divalent Ci-Cis, for example Ci-Cs, alkyleneoxy group linked to the Si via an SiC bond;
  • Q' is an anion such as a halide ion, in particular chloride, or an organic acid salt (for example acetate); r represents a mean statistical value from 2 to 20 and in particular from 2 to 8; s represents a mean statistical value from 20 to 200 and in particular from 20 to 50.
  • R7 independently represents a monovalent hydrocarbon-based group containing from 1 to 18 carbon atoms, and in particular a Ci-Cis alkyl group, a C2-C18 alkenyl group or a ring containing 5 or 6 carbon atoms, for example methyl;
  • Rs independently represents a divalent hydrocarbon-based group, in particular a Ci- Ci8 alkylene group or a divalent Ci-Cis, for example Ci-Cs, alkyleneoxy group linked to the Si via a SiC bond;
  • Rs independently represents a hydrogen atom, a monovalent hydrocarbon-based group containing from 1 to 18 carbon atoms, and in particular a Ci-Cis alkyl group, a C2-C18 alkenyl group or a -Rs-NHCOR 7 group;
  • X is an anion such as a halide ion, in particular chloride, or an organic acid salt (for example acetate); r represents a mean statistical value from 2 to 200 and in particular from 5 to 100; These silicones are described, for example, in patent application EP -A 0 530 974.
  • Ri, R2, R3 and R4 independently denote a C1-C4 alkyl group or a phenyl group
  • R5 denotes a C1-C4 alkyl group or a hydroxy group; m is an integer ranging from 1 to 5; n is an integer ranging from 1 to 5; and in which x is chosen such that the amine number is between 0.01 and 1 meq/g;
  • Multiblock polyoxyalkylenated aminosilicones of type (AB) n , A being a polysiloxane block and B being a polyoxyalkylenated block containing at least one amine group.
  • Said silicones are preferably constituted of repeating units having the following general formula: or alternatively in which: a is an integer greater than or equal to 1, preferably ranging from 5 to 200, more particularly ranging from 10 to 100; b is an integer comprised between 0 and 200, preferably ranging from 4 to 100, more particularly between from 5 and 30; x is an integer ranging from 1 to 10,000, more particularly from 10 to 5,000;
  • R" is a hydrogen atom or a methyl
  • R independently represents a divalent linear or branched C2-C12 hydrocarbon-based group, optionally including one or more heteroatoms such as oxygen; preferably, R independently denotes an ethylene group, a linear or branched propylene group, a linear or branched butylene group, or a -CH 2 CH2CH2OCH(OH)CH2- group; preferentially R independently denotes a -CH2CH 2 CH2OCH(OH)CH 2 - group;
  • R' independently represent a divalent linear or branched C2-C12 hydrocarbon-based group, optionally including one or more heteroatoms such as oxygen; preferably, R' denotes an ethylene group, a linear or branched propylene group, a linear or branched butylene group, or a -CH 2 CH2CH2OCH(OH)CH 2 - group; preferentially R' denotes - CH(CH 3 )-CH 2 -.
  • the siloxane blocks preferably represent between 50 and 95 mol% of the total weight of the silicone, more particularly from 70 to 85 mol%.
  • the amine content is preferably between 0.02 and 0.5 meq/g of the copolymer in a 30% solution of dipropylene glycol, more particularly between 0.05 and 0.2.
  • the weight-average molecular weight (Mw) of the above aminosilicone is preferably between 5,000 and 1,000,000, more particularly between 10,000 and 200,000.
  • R, R' and R" independently represent a C1-C4 alkyl or hydroxy group
  • A represents a C3 alkylene group
  • m and n are such that the weight-average molecular mass of the compound is between 5,000 and 500,000 approximately; in which: x and y are numbers ranging from 1 to 5,000; preferably, x ranges from 10 to 2,000 and especially from 100 to 1,000; preferably, y ranges from 1 to 100;
  • R1 and R2 independently preferably identical, are linear or branched, saturated or unsaturated alkyl groups, comprising 6 to 30 carbon atoms, preferably 8 to 24 carbon atoms and especially 12 to 20 carbon atoms;
  • A denotes a linear or branched alkylene group containing from 2 to 8 carbon atoms.
  • A comprises 3 to 6 carbon atoms, especially 4 carbon atoms; preferably, A is branched.
  • R1 and R2 are independently saturated linear alkyl groups comprising 6 to 30 carbon atoms, preferably 8 to 24 carbon atoms and especially 12 to 20 carbon atoms; mention may be made in particular of dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl groups; and preferentially, R1 and R2, which may be identical or different, are chosen from hexadecyl (cetyl) and octadecyl (stearyl) groups.
  • the silicone is of formula (K) with: x ranging from 10 to 2,000 and especially from 100 to 1,000; y ranging from 1 to 100;
  • A comprising 3 to 6 carbon atoms and especially 4 carbon atoms; preferably, A is branched; and more particularly A is chosen from the following divalent groups: - CH 2 CH 2 CH 2 - and -CH 2 CH(CH 3 )CH 2 -; and
  • a preferred silicone of formula (K) is bis-cetearyl amodimethicone.
  • n and m are such that the weight-average molecular weight of the silicone is between 1,000 and 55,000.
  • silicone (B) mention may be made of those sold under the names AMS-132, AMS- 152, AMS- 162, AMS- 163, AMS-191 and AMS-1203 by the company Gelest and KF-8015 by the company Shin-Etsu Chemical.
  • n is such that the weight-average molecular weight of the silicone is between 500 and 3,000.
  • silicone (C) mention may be made of those sold under the names MCR-A11 and MCR-A12 by the company Gelest.
  • the (c) aminosilicone according to the present invention is amodimethicone such as the amodimethicone sold under the name KF 8020 from the supplier Shin-Etsu Chemical, or the tradename SILSOFT 253 from the supplier MOMENTIVE PERFORMANCE MATERIALS.
  • Another preferred aminosilicone is an amodimethicone of formula (F) sold under the tradename XIAMETER® MEM-8299 Cationic Emulsion by Dow.
  • the (c) aminosilicone according to the present invention is chosen from bis-cetearyl amodimethicone (sold under the name SILSOFT AX by Momentive).
  • aminosilicone that may be used in the composition of the present invention is aminopropyldimethicone, for example, aminopropyldimethicone sold under the name KF-8015 from Shin-Etsu Chemical.
  • Aminosilicones suitable for use according to the present invention include, but are not limited to, volatile and non-volatile, cyclic, linear, and branched aminosilicones having a viscosity ranging from 5 x 1 O' 6 to 2.5 m 2 /s at 25°C, for example, from IxlO -5 to 1 m 2 /s.
  • the (c) aminosilicone be selected from the group consisting of amodimethicone, aminopropyldimethicone, and a mixture thereof.
  • the amount of the (c) amino silicone(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.05% by weight or more, and more preferably 0.1% by weight or more, relative to the total weight of the composition.
  • the amount of the (c) aminosilicone(s) in the composition according to the present invention may be from 0.01% to 10% by weight, preferably from 0.05% to 5% by weight, and more preferably from 0.1% to 1% by weight, relative to the total weight of the composition.
  • composition according to the present invention may comprise (d) water.
  • the composition according to the present invention comprises (d) water
  • the composition according to the present invention is not anhydrous.
  • the amount of the (d) water in the composition according to the present invention may be 20% by weight or more, preferably 30% by weight or more, and more preferably 40% by weight or more relative to the total weight of the composition.
  • the amount of the (d) water in the composition according to the present invention may be from 20% to 95% by weight, preferably from 30% to 90% by weight, and more preferably from 40% to 85% by weight relative to the total weight of the composition.
  • composition according to the present invention may comprise (e) at least one betaine compound.
  • a single type of (e) betaine compound may be used, or two or more different types of (e) betaine compounds may be used in combination.
  • betaine compound here means an amphoteric compound having a positively charged cationic moiety and a negatively charged anionic moiety, wherein no hydrogen atom is bound to a positively charged atom in the positively charged cationic moiety and the positively charged cationic moiety may not be adjacent to the negatively charged anionic moiety.
  • the (e) betaine compound here is not a surfactant, which comprises at least one hydrophilic part and at least one hydrophobic part.
  • the positively charged cationic moiety in the (e) betaine compound includes, but is not limited to, a quaternary ammonium cation, a phosphonium cation, and a sulfonium cation.
  • the (e) betaine compound includes a quaternary ammonium cation as the positively charged cationic moiety.
  • the negatively charged anionic moiety in the (e) betaine compound includes, but is not limited to, a carboxylate anion.
  • the (e) betaine compound may be selected from the group consisting of trimethylglycine, carnitine, L-proline betaine or stachydrine, and mixtures thereof, and may preferably be trimethylglycine.
  • the amount of the (e) betaine compound(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.05% by weight or more, and more preferably 0.1% by weight or more relative to the total weight of the composition.
  • the amount of the (e) betaine compound(s) in the composition according to the present invention may be 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less relative to the total weight of the composition.
  • the amount of the (e) betaine compound(s) in the composition according to the present invention may range from 0.01% to 15% by weight, preferably from 0.05% to 10% by weight, and more preferably from 0.1% to 5% by weight relative to the total weight of the composition.
  • composition according to the present invention may comprise (f) at least one fatty amine.
  • Two or more fatty amines may be used in combination.
  • a single type of a fatty amine or a combination of different types of fatty amines may be used.
  • fatty amines is understood to mean primary, secondary or tertiary fatty amines, which are optionally (poly)oxyalkylenated, or salts thereof.
  • the fatty amines generally comprise at least one C6-C30 hydrocarbon-based chain.
  • the fatty amines according to the present invention are not quatemized.
  • the fatty amines according to the present invention are not (poly)oxyalkylenated.
  • the composition according to the present invention comprises (f) at least one fatty amine comprising at least one C6-C30 hydrocarbon-based chain.
  • the composition according to the present invention comprises (f) at least one fatty amine chosen from tertiary fatty amines.
  • composition according to the present invention comprises one or more tertiary fatty amines chosen from fatty amidoamines.
  • the (f) fatty amine that may be used in the context of the present invention may be chosen from fatty amines having the formula (IV) below:
  • R represents a monovalent hydrocarbon-based radical containing from 6 to 30 carbon atoms, preferably from 8 to 24 carbon atoms, and in particular a linear or branched, saturated or unsaturated and substituted or unsubstituted C6-C30, preferably C8-C24, alkyl radical, preferably a linear or branched C6-C30, better still C8-C24, alkyl radical, or a linear or branched C6-C30, preferably C8-C24, alkenyl radical; and
  • R’ which may be identical or different, represent a linear or branched, saturated or unsaturated and substituted or unsubstituted monovalent hydrocarbon-based radical containing less than 6 carbon atoms, preferably from 1 to 4 carbon atoms, preferably a methyl radical.
  • the (f) fatty amine corresponding to the above formula (IV) may be chosen, for example, from dimethyllauramine, dimethylbehenamine, dimethylcocamine, dimethylmyristamine, dimethylpalmitamine, dimethylstearamine, dimethyltallowamine, dimethylsoyamine, and mixtures thereof.
  • fatty amine that may be used in the context of the present invention may also be chosen from fatty amidoamines, preferably fatty amidoamines having the formula (V) below:
  • R represents a monovalent hydrocarbon-based radical containing from 5 to 29 carbon atoms, preferably from 7 to 23 carbon atoms, and in particular a linear or branched, saturated or unsaturated and substituted or unsubstituted C5-C29, preferably C7-C23, alkyl radical, preferably a linear or branched C5-C29, better still C5-C23, alkyl radical, or a linear or branched C5-C29, preferably C7-C23, alkenyl radical;
  • R which may be identical or different, represent a divalent hydrocarbon-based radical containing less than 6 carbon atoms, preferably 2 or 3 carbon atoms;
  • R’ which may be identical or different, represent a linear or branched, saturated or unsaturated and substituted or unsubstituted monovalent hydrocarbon-based radical containing less than 6 carbon atoms, preferably from 1 to 4 carbon atoms, preferably a methyl radical.
  • the (f) fatty amine corresponding to the above formula (V) may be chosen, for example, from oleamidopropyl dimethylamine, stearamidopropyl dimethylamine sold by the company Inolex Chemical Company under the name Lexamine SI 3, iso stearamidopropyl dimethylamine, stearamidoethyl dimethylamine, lauramidopropyl dimethylamine, myristamidopropyl dimethylamine, behenamidopropyl dimethylamine, dilinoleamidopropyl dimethylamine, palmitamidopropyl dimethylamine, ricinoleamidopropyl dimethylamine, soyamidopropyl dimethylamine, avocadoamidopropyl dimethylamine, cocamidopropyl dimethylamine, minkamidopropyl dimethylamine, oatamidopropyl dimethylamine, sesamidopropyl dimethylamine, tallamidopropyl dimethylamine, oli
  • the (f) fatty amine may be chosen from fatty amidoamines, preferentially from fatty amidoamines of the above formula (V).
  • the (f) fatty amine is stearamidopropyl dimethylamine.
  • R denotes a C17 alkyl group for stearamidopropyl dimethylamine.
  • composition according to the present invention comprises stearamidopropyl dimethylamine.
  • the amount of the (I) fatty amine(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.1% by weight or more, and more preferably 1 % by weight or more, relative to the total weight of the composition.
  • the amount of the (f) fatty amine(s) in the composition according to the present invention may be 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.
  • the amount of the (f) fatty amine(s) in the composition according to the present invention may be from 0.01% to 15% by weight, preferably from 0.1% to 10% by weight, and more preferably from 1% to 5% by weight, relative to the total weight of the composition.
  • composition according to the present invention may comprise (g) at least one oil. Two or more oils may be used in combination. Thus, a single type of oil or a combination of different types of oils may be used.
  • oil means a fatty compound or substance which is in the form of a liquid or a paste or a solid at room temperature (25°C) under atmospheric pressure (760 mmHg).
  • oil(s) those generally used in cosmetics can be used alone or in combination. These oils may be volatile or non-volatile.
  • the (g) oil may be a non-polar oil such as a hydrocarbon oil, a silicone oil, or the like; a polar oil such as a plant or animal oil and an ester oil or an ether oil; or a mixture thereof.
  • the (g) oil may be selected from the group consisting of oils of plant or animal origin, synthetic oils, silicone oils, and hydrocarbon oils.
  • alkane oils such as isododecane and isohexadecane
  • ester oils such as isododecane and isohexadecane
  • ether oils such as triglycerides
  • the ester oils are preferably liquid esters of saturated or unsaturated, linear or branched Ci- C26 aliphatic monoacids or polyacids and of saturated or unsaturated, linear or branched Ci- C26 aliphatic monoalcohols or polyalcohols, the total number of carbon atoms of the esters being greater than or equal to 10.
  • At least one from among the alcohol and the acid from which the esters of the present invention are derived is branched.
  • ethyl palmitate ethyl hexyl palmitate
  • isopropyl palmitate dicaprylyl carbonate
  • alkyl myristates such as isopropyl myristate or ethyl myristate
  • cetyl palmitate isocetyl stearate
  • 2-ethylhexyl isononanoate isononyl isononanoate
  • isodecyl neopentanoate isostearyl neopentanoate.
  • esters of C4-C22 dicarboxylic or tricarboxylic acids and of C1-C22 alcohols and esters of monocarboxylic, dicarboxylic or tricarboxylic acids and of non-sugar C4-C26 dihydroxy, trihydroxy, tetrahydroxy or pentahydroxy alcohols may also be used.
  • sugar esters and diesters of C6-C30 and preferably C12-C22 fatty acids.
  • sucrose means oxygen-bearing hydrocarbon-based compounds containing several alcohol functions, with or without aldehyde or ketone functions, and which comprise at least 4 carbon atoms. These sugars may be monosaccharides, oligosaccharides or polysaccharides.
  • suitable sugars include sucrose (or saccharose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose, and derivatives thereof, especially alkyl derivatives, such as methyl derivatives, for instance methylglucose.
  • the sugar esters of fatty acids may be chosen especially from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C6-C30 and preferably C12-C22 fatty acids. If they are unsaturated, these compounds may have one to three conjugated or non-conjugated carbon-carbon double bonds.
  • esters according to this variant may also be selected from monoesters, diesters, triesters, tetraesters and polyesters, and mixtures thereof.
  • esters may be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates, or mixtures thereof such as, especially, oleopalmitate, oleostearate and palmitostearate mixed esters, as well as pentaerythrityl tetraethyl hexanoate.
  • monoesters and diesters and especially sucrose, glucose or methylglucose monooleates or dioleates, stearates, behenates, oleopalmitates, linoleates, linolenates and oleostearates.
  • ester oils mention may be made of, for example, diisopropyl adipate, dioctyl adipate, 2-ethylhexyl hexanoate, ethyl laurate, cetyl octanoate, octyldodecyl octanoate, isodecyl neopentanoate, myristyl propionate, 2-ethylhexyl 2-ethylhexanoate, 2- ethylhexyl octanoate, 2-ethylhexyl caprylate/caprate, methyl palmitate, ethyl palmitate, isopropyl palmitate, dicaprylyl carbonate, isopropyl lauroyl sarcosinate, isononyl isononanoate, ethylhexyl palmitate, isohexyl laurate, hexyl laur
  • artificial triglycerides mention may be made of, for example, capryl caprylyl glycerides, glyceryl trimyristate, glyceryl tripalmitate, glyceryl trilinolenate, glyceryl trilaurate, glyceryl tricaprate, glyceryl tricaprylate, glyceryl tri(caprate/caprylate) and glyceryl tri (caprate/ caprylate/linolenate) .
  • capryl caprylyl glycerides glyceryl trimyristate, glyceryl tripalmitate, glyceryl trilinolenate, glyceryl trilaurate, glyceryl tricaprate, glyceryl tricaprylate, glyceryl tri(caprate/caprylate) and glyceryl tri (caprate/ caprylate/linolenate) .
  • silicone oils mention may be made of, for example, linear organopolysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, and the like; cyclic organopolysiloxanes such as cyclohexasiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, and the like; and mixtures thereof.
  • linear organopolysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, and the like
  • cyclic organopolysiloxanes such as cyclohexasiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodeca
  • the silicone oils are chosen from liquid polydialkylsiloxanes, especially liquid polydimethylsiloxanes (PDMS) and liquid polyorganosiloxanes comprising at least one aryl group.
  • PDMS liquid polydimethylsiloxanes
  • silicone oils may also be organomodified.
  • organomodified silicones that can be used in accordance with the present invention are silicone oils as defined above and comprise in their structure one or more organofunctional groups attached via a hydrocarbon-based group.
  • Organopolysiloxanes are defined in greater detail in Walter Noll’s Chemistry and Technology of Silicones (1968), Academic Press. They may be volatile or non-volatile.
  • cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably 4 to 5 silicon atoms.
  • cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably 4 to 5 silicon atoms.
  • These are, for example, octamethylcyclotetrasiloxane sold in particular under the name Volatile Silicone® 7207 by Union Carbide or Silbione® 70045 V2 by Rhodia, decamethylcyclopentasiloxane sold under the name Volatile Silicone® 7158 by Union Carbide, Silbione® 70045 V5 by Rhodia, and dodecamethylcyclopentasiloxane sold under the name Silsoft 1217 by Momentive Performance Materials, and mixtures thereof. Mention may also be made of cyclocopolymers of the type such as dimethylsiloxane/methylalkylsiloxane, such as Silicone Volatile® FZ 3109 sold by the company Union Carbide, of formula:
  • Non-volatile polydialkylsiloxanes may also be used. These non-volatile silicones are more particularly chosen from polydialkylsiloxanes, among which mention may be made mainly of polydimethylsiloxanes containing trimethylsilyl end groups.
  • polydialkylsiloxanes mention may be made, in a non-limiting manner, of the following commercial products: the Silbione® oils of the 47 and 70 047 series or the Mirasil® oils sold by Rhodia, for instance the oil 70 047 V 500 000; the oils of the Mirasil® series sold by the company Rhodia; the oils of the 200 series from the company Dow Coming, such as DC200 with a viscosity of 60 000 mm 2 /s; the Viscasil® oils from General Electric and certain oils of the SF series (SF 96, SF 18) from General Electric.
  • the Silbione® oils of the 47 and 70 047 series or the Mirasil® oils sold by Rhodia for instance the oil 70 047 V 500 000
  • the oils of the Mirasil® series sold by the company Rhodia the oils of the 200 series from the company Dow Coming, such as DC200 with a viscosity of 60 000 mm 2 /s
  • the Viscasil® oils from General Electric and certain oils of the SF
  • CTFA dimethiconol
  • silicones containing aryl groups are polydiarylsiloxanes, especially polydiphenylsiloxanes and polyalkylarylsiloxanes.
  • examples that may be mentioned include the products sold under the following names: the Silbione® oils of the 70 641 series from Rhodia; the oils of the Rhodorsil® 70 633 and 763 series from Rhodia; the oil DOWSILTM556 Cosmetic Grade Fluid from Dow; the silicones of the PK series from Bayer, such as the product PK20; certain oils of the SF series from General Electric, such as SF 1023, SF 1154, SF 1250 and SF 1265.
  • Hydrocarbon oils may be chosen from: linear or branched, optionally cyclic, Ce-Ci6 lower alkanes. Examples that may be mentioned include hexane, undecane, dodecane, tridecane and isoparaffins, for instance isohexadecane, isododecane and isodecane; and linear or branched hydrocarbons containing more than 16 carbon atoms, such as liquid paraffins, liquid petroleum jelly, polydecenes and hydrogenated polyisobutenes such as Parleam®, and squalane.
  • the (g) oil be chosen from polar oils, more preferably ester oils, and even more preferably monoester oils.
  • the amount of the (g) oil(s) in the composition according to the present invention may be 1% by weight or more, preferably 3% by weight or more, and more preferably 5% by weight or more relative to the total weight of the composition.
  • the amount of the (g) oil(s) in the composition according to the present invention may be 40% by weight or less, preferably 30% by weight or less, and more preferably 20% by weight or less relative to the total weight of the composition.
  • the amount of (g) oil(s) in the composition according to the present invention may be from 1% to 40% by weight, preferably from 3% to 30% by weight, and more preferably from 5% to 20% by weight relative to the total weight of the composition.
  • composition according to the present invention may comprise (h) at least one fatty alcohol.
  • a single type of fatty alcohol may be used, or two or more different types of fatty alcohols may be used in combination.
  • fatty here means the inclusion of a relatively large number of carbon atoms.
  • alcohols which have 6 or more, preferably 8 or more, and more preferably 10 or more carbon atoms are encompassed within the scope of fatty alcohols.
  • the fatty alcohols may be saturated or unsaturated.
  • the fatty alcohol may be linear or branched. Two or more fatty alcohols may be used in combination.
  • the (h) fatty alcohol may have the structure R-OH wherein R is chosen from saturated and unsaturated, linear and branched radicals containing from 8 to 40 carbon atoms, for example from 8 to 30 carbon atoms. In at least one embodiment, R is chosen from C12-C24 alkyl and C12-C24 alkenyl groups. R may be or may not be substituted with at least one hydroxyl group.
  • Non-limiting examples of the (h) fatty alcohols include lauryl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, linoleyl alcohol, undecylenyl alcohol, palmitoleyl alcohol, arachidonyl alcohol, erucyl alcohol, cetearyl alcohol, and a mixture thereof.
  • Suitable fatty alcohols include, but are not limited to, cetyl alcohol, cetearyl alcohol, stearyl alcohol, behenyl alcohol, oleyl alcohol, and a mixture thereof.
  • the fatty alcohol used in the composition according to the present invention is chosen from a mixture of cetyl alcohol and stearyl alcohol (cetearyl alcohol).
  • the (h) fatty alcohol be selected from the group consisting of cetyl alcohol, cetearyl alcohol, and stearyl alcohol.
  • the amount of the (h) fatty alcohol(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.1% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition.
  • the amount of the (h) fatty alcohol(s) in the composition according to the present invention may be 20% by weight or less, preferably 5% by weight or less, and more preferably 10% by weight or less, relative to the total weight of the composition.
  • the amount of the (h) fatty alcohol(s) in the composition according to the present invention may range from 0.01% to 20% by weight, preferably from 0.1% to 15% by weight, and more preferably from 1% to 10% by weight, relative to the total weight of the composition.
  • composition according to the present invention may have a pH of 7 or less, preferably 6 or less, and more preferably 5 or less, which is measured at 25°C.
  • composition according to the present invention may have a pH of 3 or more, which is measured at 25°C.
  • composition according to the present invention may have a pH of from 3 to 7, preferably from 3 to 6, and more preferably from 3 to 5, which is measured at 25°C.
  • composition according to the present invention may comprise at least one alkaline agent.
  • Two or more alkaline agents may be used in combination.
  • a single type of alkaline agent or a combination of different types of alkaline agents may be used.
  • the alkaline agent is different from the (f) fatty amine.
  • composition according to the present invention include alkaline agent(s), if the (a) compound or the (b) compound can function to reduce the pH of the composition.
  • the alkaline agent may be an inorganic alkaline agent. It is preferable that the alkaline agent be non-volatile. It is preferable that the inorganic alkaline agent be selected from the group consisting of alkaline metal hydroxides; alkaline earth metal hydroxides; and alkaline metal phosphates and monohydrogen phosphates such as sodium phosphate or sodium monohydrogen phosphate.
  • inorganic alkaline metal hydroxides mention may be made of sodium hydroxide, lithium hydroxide and potassium hydroxide.
  • alkaline earth metal hydroxides mention may be made of calcium hydroxide and magnesium hydroxide.
  • sodium hydroxide and potassium hydroxide are preferable.
  • the alkaline agent may be an organic alkaline agent. It is preferable that the organic alkaline agent be selected from the group consisting of monoamines and diamines.
  • alkanolamines such as mono-, di- and tri-ethanolamine, comprising 1 to 3 hydroxyalkyl (C1-C4) groups.
  • alkanolamines may be selected from monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine, N,N-dimethylethanolamine, 2-amino-2-methyl- 1-propanol, triisopropanolamine, 2-amino-2-methyl-l,3-propanediol, 3-amino-l,2- propanediol, 3 -dimethylamino- 1,2-propanediol, and tris(hydroxymethylamino)methane.
  • the diamines may be described by the structure (B) below: wherein W denotes an alkylene such as propylene optionally substituted by a hydroxyl or a C1-C4 alkyl radical, and R a , Rb, Rc and Rd independently denote a hydrogen atom, an alkyl radical or a C1-C4 hydroxyalkyl radical, which may be exemplified by 1,3 -propanediamine and derivatives thereof.
  • W denotes an alkylene such as propylene optionally substituted by a hydroxyl or a C1-C4 alkyl radical
  • R a , Rb, Rc and Rd independently denote a hydrogen atom, an alkyl radical or a C1-C4 hydroxyalkyl radical, which may be exemplified by 1,3 -propanediamine and derivatives thereof.
  • the amount of the alkaline agent(s) in the composition according to the present invention may be 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.
  • the amount of the alkaline agent(s) in the composition according to the present invention may be from 0.01% to 15% by weight, preferably from 0.05% to 10% by weight, and more preferably from 0.1% to 5% by weight, relative to the total weight of the composition.
  • composition according to the present invention may comprise at least one acid which is different from the (a) compound or the (b) compound. Two or more acids may be used in combination. Thus, a single type of acid or a combination of different types of acids may be used.
  • the acid may be used to adjust the pH of the composition according to the present invention.
  • HC1 hydrochloric acid
  • the amount of the acid(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.05% by weight or more, and more preferably 0.1% by weight or more, relative to the total weight of the composition.
  • the amount of the acid(s) in the composition according to the present invention may be 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.
  • the amount of the acid(s) in the composition according to the present invention may be from 0.01% to 15% by weight, preferably from 0.05% to 10% by weight, and more preferably from 0.1% to 5% by weight, relative to the total weight of the composition.
  • composition according to the present invention may also comprise at least one other optional ingredient, chosen in particular from: anionic and amphoteric surfactants; thickeners; sunscreens; moisturizers; antidandruff agents; antioxidants; antibacterial agents such as benzoic acid; preservatives such as phenoxyethanol; chelating agents; nacreous agents and opacifiers; plasticizers or coalescers; fillers; emulsifiers; polymers, in particular conditioning polymers, such as cationic polymers; fragrances; silanes; crosslinking agents; and surfactants including anionic, cationic, amphoteric and nonionic surfactants.
  • the composition can, of course, comprise several cosmetic ingredients appearing in the above list.
  • composition according to the present invention may include one or several cosmetically acceptable organic solvents, which may be alcohols: in particular monovalent alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol, and phenylethyl alcohol; diols such as ethylene glycol, propylene glycol, and caprylyl glycol; other polyols such as glycerol; and ethers such as ethylene glycol monomethyl, monoethyl, and monobutyl ethers, propylene glycol monomethyl, monoethyl, and monobutyl ethers, and butylene glycol monomethyl, monoethyl, and monobutyl ethers.
  • alcohols in particular monovalent alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol, and phenylethyl alcohol; diols such as ethylene glycol, propylene glycol, and caprylyl glycol; other polyols such as glycerol
  • the above optional ingredient(s) can be present in normal amounts which can be easily determined by those skilled in the art and which can be, for each ingredient, between 0.01% and 80% by weight. Those skilled in the art will take care to choose the ingredients included in the composition, and also the amounts thereof, such that they do not harm the properties of the compositions used for the present invention.
  • the composition according to the present invention be free of ammonia or thiol compound.
  • free of ammonia or thiol compound means that the composition according to the present invention does not include a substantial amount of ammonia or a thiol compound.
  • the composition according to the present invention includes 1% by weight or less, more preferably 0.5% by weight or less, and even more preferably 0.1% by weight or less of ammonia or thiol compound, in particular no ammonia or thiol compound.
  • the thiol compound here means a compound which has at least one thiol (-SH) group.
  • the thiol compound may be a reducing agent.
  • the thiol reducing agent may be chosen from the group consisting of thioglycolic acid and derivatives thereof, in particular esters thereof such as glycerol or glycol monothioglycolate; thiolactic acid and derivatives thereof, in particular esters thereof such as glycerol monothiolactate; 3 -mercaptopropionic acid and derivatives thereof, in particular esters thereof such as glycerol 3 -mercaptopropionate and ethyleneglycol 3 -mercaptopropionate; cysteamine and derivatives thereof, in particular C1-C4 acyl derivatives thereof such as N-acetylcysteamine and N-propionylcysteamine; monothioglycerol and derivatives thereof, in particular esters; cysteine and derivatives thereof, in particular esters such as N-acetylcysteine, N-alkanoylcysteine and cysteine alkyl
  • salts mention may be made of, for example, ammonium salts; primary-, secondary- or tertiary-amine salts; alkaline metal salts; and alkaline earth metal salts.
  • primary-, secondary- or tertiary-amine for example, monoethanolamine, di-isopropanolamine or triethanolamine, respectively, may be mentioned.
  • alkylamindmercaptoalkylamides such as those described in European Patent Application No. 0 514282; (2/3) hydroxy-2 propyl thioglycolate; and the hydroxy-2 methyl-1 ethyl thioglycolate-based mixture (67/33) described in French Patent Application No. 2 679 448.
  • the term “free of a reducing agent or an oxidizing agent” means that the composition according to the present invention does not include a substantial amount of a reducing agent or an oxidizing agent.
  • the composition according to the present invention includes 1% by weight or less, more preferably 0.5% by weight or less, and even more preferably 0.1% by weight or less of a reducing agent or an oxidizing agent, in particular no reducing agent or no oxidizing agent.
  • the reducing agent may be a thiol reducing agent or a non-thiol reducing agent.
  • the thiol reducing agent is as described above.
  • the non-thiol reducing agent here means a reducing agent with no thiol group.
  • the non- thiol reducing agent may be chosen from the group consisting of sulfites, bisulfites, sulfinates, phosphines, sugars, reductones and hydrides.
  • the non-thiol 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.
  • compositions used for the present invention may be in any form suitable for topical application, and in particular in the form of an aqueous, alcoholic or aqueous-alcoholic, or oily solution or suspension; a solution or a dispersion of a lotion or serum type; an emulsion, in particular of liquid or semi-liquid consistency, of O/W, W/O or multiple type (if the composition according to the present invention includes at least one oil); a suspension or emulsion of a soft consistency of cream (O/W) or (W/O) type; an aqueous gel; or any other cosmetic form.
  • composition according to the present invention can be used for treating, preferably reshaping, and more preferably straightening keratin fibers such as hair.
  • the present invention also relates to a process for reshaping, preferably straightening, keratin fibers, such as hair, comprising the steps of:
  • the process according to the present invention is for the purpose of reshaping, preferably straightening, keratin fibers such as hair, more preferably straightening for a long period of time, and even more preferably straightening even after shampooing several times.
  • the process according to the present invention can be a semi-permanent reshaping, preferably straightening, process.
  • the keratin fibers be cleaned before the step (i).
  • This cleaning step may be performed by, for example, shampooing the keratin fibers, followed by rinsing off the keratin fibers. After rinsing off, the keratin fibers may be dried. It is preferable that the keratin fibers are wet just before the step (i).
  • the composition according to the present invention which is explained above, is applied to keratin fibers such as hair.
  • the application of the composition according to the present invention may be performed by any means, such as a brush or a comb.
  • the bath ratio of the applied composition according to the present invention to the keratin fibers may range from 0.1 to 10, more particularly from 0.5 to 5, and preferably between 0.3 and 2.
  • the term "bath ratio" is intended to mean the weight ratio between the total weight of the applied composition and the total weight of the keratin fibers.
  • the keratin fibers be left as they are for a certain amount of time; typically from 1 minute to 1 hour, preferably from 2 to 30 minutes, and more preferably from 3 to 10 minutes, if necessary, in order to let the composition penetrate into the keratin fibers.
  • the process according to the present invention may comprise the optional step (ii) of rinsing off the keratin fibers with or without drying the keratin fibers after being rinsed off.
  • the keratin fibers are rinsed off in order to remove the composition according to the present invention from the keratin fibers.
  • the step of rinsing may be performed with water. It is preferable that the keratin fibers be dried after being rinsed off.
  • the drying of the keratin fibers can be performed with a conventional drying means such as a hair dryer.
  • the heating iron any conventional heating iron can be used.
  • the heating iron can have at least one plate, preferably two plates, which can be heated by, for example, electric heating.
  • the heated plate(s) can be applied onto the keratin fibers and moved along with the direction of the keratin fibers to straighten them.
  • the heating iron has two plates, and that keratin fibers are sandwiched between the two plates of the heating iron, in which at least one of the plates can be heated, and then the two plates are moved along the direction of the keratin fibers to straighten them.
  • the heating iron in particular a part thereof contacting with keratin fibers, such as a heating plate or heating plates, has a temperature of more than 50°C and less than 250°C, more preferably more than 100°C and less than 240°C, and even more preferably more than 150°C and less than 230°C.
  • the step (iii) can be performed by one or more strokes of moving the heating iron along with the direction of keratin fibers.
  • the step (iii) can be controlled by not only the temperature of the heating iron but also the number of strokes of the heating iron.
  • any conventional heating curler can be used. If the keratin fibers are rolled around a heating curler, this rolling-up may be performed on the entire length of the keratin fibers or, for example, on half the length of the keratin fibers. Depending on, for example, the desired hairstyle shape and amount of curls, the rolling-up may be performed with more or less thick locks.
  • the heating curler in particular a part thereof contacting with keratin fibers, such as a heating rod and a heating cover, has a temperature of more than 50°C and less than 250°C, more preferably more than 100°C and less than 240°C, and even more preferably more than 150°C and less than 230°C.
  • the step (iii) can be performed by maintaining keratin fibers on a heating curler such that mechanical tension is applied on the keratin fibers.
  • the step (iii) can be controlled by not only the temperature of the heating curler but also the strength of the mechanical tension.
  • the heating time may depend on the temperature of the heating curler but also on the strength of the mechanical tension. It may be, for example, from 1 second to 10 minutes, and preferably from a few seconds to 5 minutes.
  • the present invention also relates to a kit for reshaping, preferably straightening, keratin fibers such as hair, comprising: at least one selected from the group consisting of an iron, a curler, a comb, a dryer, and a combination thereof, preferably at least one heating iron, heating curler, heating comb or heating dryer which is capable of providing the keratin fibers with a temperature of more than 50°C, preferably more than 100°C, and more preferably more than 150°C; and the composition according to the present invention.
  • Any conventional iron or curler including any conventional heating iron or heating curler, may be used as the above iron or curler in the kit according to the present invention.
  • the heater in the kit is not limited as long as it can heat keratin fibers at a temperature of more than 50°C, preferably more than 100°C, and more preferably more than 150°C.
  • This temperature may be less than 250°C, preferably less than 240°C, and more preferably less than 230°C.
  • this temperature may be more than 50°C and less than 250°C, preferably more than 100°C and less than 240°C, and more preferably more than 150°C and less than
  • the iron or curler, as well as the composition, in the kit according to the present invention may be used as explained in the section titled [Process] above.
  • composition used in the kit according to the present invention.
  • the present invention may relate to a use of (c) at least one aminosilicone in a composition for reshaping, preferably straightening, keratin fibers such as hair, preferably with heating, comprising:
  • the heating is not limited as long as it can heat keratin fibers at a temperature of more than 50°C, preferably more than 100°C, and more preferably more than 150°C.
  • This temperature may be less than 250°C, preferably less than 240°C, and more preferably less than 230°C.
  • this temperature may be more than 50°C and less than 250°C, preferably more than 100°C and less than 240°C, and more preferably more than 150°C and less than 230°C.
  • composition may further comprise (d) water and/or (e) at least one betaine compound and/or (f) at least one fatty amine and/or (g) at least one oil and/or (h) at least one fatty alcohol.
  • compositions according to Examples 1-4 and Comparative Example 1 were prepared by mixing the ingredients shown in Table 1. The numerical values for the amounts of the ingredients are all based on “% by weight” as raw materials. The concentration of amodimethicone or aminopropyldimethicone in the composition according to Examples 1-4 was adjusted to be 0.5% by weight, relative to the total weight of the composition.
  • compositions were used to straighten a hair swatch, and then the hair swatch was evaluated, in accordance with the following protocols.
  • a hair swatch of Chinese black natural, slightly wavy hair, in a length of 27 cm was shampooed with the SLES shampoo, whose composition is shown in Table 2 below. The hair swatch was rinsed off thoroughly with tap water.
  • the hair swatch was blow-dried with a hair dryer (Nobby NB3100, TESCOM DENKI Co., Ltd, Japan) for about 90 seconds until dried.
  • a hair dryer Nobby NB3100, TESCOM DENKI Co., Ltd, Japan
  • the hair swatch was subjected to straightening by 3 strokes with a hair straightening iron (ADST Premium DS2, Hakko Limited, Japan) at 180°C for 4 seconds/stroke.
  • ADST Premium DS2, Hakko Limited, Japan a hair straightening iron

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Abstract

La présente invention concerne principalement une composition pour les fibres de kératine, telles que des cheveux, comprenant : (a) au moins un composé choisi dans le groupe constitué par l'acide glyoxylique, les solvates d'acide glyoxylique, les sels d'acide glyoxylique, les esters d'acide glyoxylique, les amides d'acide glyoxylique, et leurs mélanges ; (b) au moins un composé, différent du composé (a), choisi dans le groupe constitué des céto-acides, de leurs sels et de leurs mélanges ; et (c) au moins une aminosilicone. La présente invention peut améliorer le coiffage de fibres de kératine telles que des cheveux sur la base du traitement des fibres de kératine avec de l'acide glyoxylique ou un dérivé de celui-ci, en offrant des effets de coiffage plus durables.
PCT/JP2024/080108 2023-07-20 2024-07-05 Composition convenant aux fibres de kératine WO2025018430A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2023118447A JP2025015195A (ja) 2023-07-20 2023-07-20 ケラチン繊維に好適な組成物
JP2023-118447 2023-07-20
FR2308992A FR3152387A3 (fr) 2023-08-28 2023-08-28 Composition adaptée aux fibres kératineuses
FR2308992 2023-08-28

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4185087A (en) 1977-12-28 1980-01-22 Union Carbide Corporation Hair conditioning compositions containing dialkylamino hydroxy organosilicon compounds and their derivatives
EP0354835A1 (fr) 1988-08-04 1990-02-14 L'oreal N-(mercaptoalkyl)oméga-hydroxyalkylamides et leur utilisation en tant qu'agents réducteurs dans un procédé de déformation permanente des cheveux
EP0368763A1 (fr) 1988-11-09 1990-05-16 L'oreal Mercapto-4 butyramides N-mono ou N,N-disubstitués par un radical mono ou polyhydroxyalkyle, et leur utilisation en tant qu'agents réducteurs dans un procédé de déformation permanente des cheveux
EP0432000A1 (fr) 1989-11-20 1991-06-12 L'oreal Composition rÀ©ductrice, pour déformation permanente des cheveux, contenant en tant qu'agent réducteur un amino mercaptoalkylamide ou l'un de ses sels, et son utilisation dans un procédé de déformation permanente des cheveux
EP0514282A1 (fr) 1991-05-17 1992-11-19 L'oreal Nouveaux alkylamino mercaptoalkylamides ou l'un de leurs sels cosmétiquement acceptables, et leur utilisation en tant qu'agents réducteurs, dans un procédé de déformation permanente des cheveux
FR2679448A1 (fr) 1991-07-23 1993-01-29 Oreal Melange azetrope de thioglycolate d'hydroxy-2 propyle et de thioglycolate d'hydroxy-2 methyl-1 ethyle, son procede d'obtention et son utilisation dans un procede de deformation permanente des cheveux.
EP0530974A1 (fr) 1991-08-05 1993-03-10 Unilever Plc Compositions pour le soin des cheveux
WO2011104282A2 (fr) * 2010-02-24 2011-09-01 Alderan S.A.S. Di D'ottavi Adele & C. Procédé de lissage semi-permanent de cheveux frisés, ondulés ou bouclés
WO2013092959A1 (fr) * 2011-12-21 2013-06-27 L'oreal Traitement capillaire au moyen d'une émulsion inverse comprenant un dérivé de dicarbonyle
WO2014072478A1 (fr) * 2012-11-09 2014-05-15 L'oreal Composition comprenant un composé dicarbonyle et un amino-silicone, et procédé de défrisage des cheveux au moyen de cette composition
WO2014131469A1 (fr) 2013-02-28 2014-09-04 Kao Corporation Composition et procédé pour le lissage semi-permanent des cheveux
WO2015036052A1 (fr) * 2013-09-16 2015-03-19 Kao Corporation Procédé de défrisage semi-permanent des cheveux et soins ultérieurs des cheveux
WO2016102206A1 (fr) * 2014-12-22 2016-06-30 Kao Germany Gmbh Procédé de traitement capillaire
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4185087A (en) 1977-12-28 1980-01-22 Union Carbide Corporation Hair conditioning compositions containing dialkylamino hydroxy organosilicon compounds and their derivatives
EP0354835A1 (fr) 1988-08-04 1990-02-14 L'oreal N-(mercaptoalkyl)oméga-hydroxyalkylamides et leur utilisation en tant qu'agents réducteurs dans un procédé de déformation permanente des cheveux
EP0368763A1 (fr) 1988-11-09 1990-05-16 L'oreal Mercapto-4 butyramides N-mono ou N,N-disubstitués par un radical mono ou polyhydroxyalkyle, et leur utilisation en tant qu'agents réducteurs dans un procédé de déformation permanente des cheveux
EP0432000A1 (fr) 1989-11-20 1991-06-12 L'oreal Composition rÀ©ductrice, pour déformation permanente des cheveux, contenant en tant qu'agent réducteur un amino mercaptoalkylamide ou l'un de ses sels, et son utilisation dans un procédé de déformation permanente des cheveux
EP0514282A1 (fr) 1991-05-17 1992-11-19 L'oreal Nouveaux alkylamino mercaptoalkylamides ou l'un de leurs sels cosmétiquement acceptables, et leur utilisation en tant qu'agents réducteurs, dans un procédé de déformation permanente des cheveux
FR2679448A1 (fr) 1991-07-23 1993-01-29 Oreal Melange azetrope de thioglycolate d'hydroxy-2 propyle et de thioglycolate d'hydroxy-2 methyl-1 ethyle, son procede d'obtention et son utilisation dans un procede de deformation permanente des cheveux.
EP0530974A1 (fr) 1991-08-05 1993-03-10 Unilever Plc Compositions pour le soin des cheveux
WO2011104282A2 (fr) * 2010-02-24 2011-09-01 Alderan S.A.S. Di D'ottavi Adele & C. Procédé de lissage semi-permanent de cheveux frisés, ondulés ou bouclés
WO2013092959A1 (fr) * 2011-12-21 2013-06-27 L'oreal Traitement capillaire au moyen d'une émulsion inverse comprenant un dérivé de dicarbonyle
WO2014072478A1 (fr) * 2012-11-09 2014-05-15 L'oreal Composition comprenant un composé dicarbonyle et un amino-silicone, et procédé de défrisage des cheveux au moyen de cette composition
EP2916806B1 (fr) * 2012-11-09 2018-12-26 L'Oréal Procede de lissage des cheveux a partir d'une composition contenant de l'acide glyoxylique et/ou un de ses derives
WO2014131469A1 (fr) 2013-02-28 2014-09-04 Kao Corporation Composition et procédé pour le lissage semi-permanent des cheveux
WO2015036052A1 (fr) * 2013-09-16 2015-03-19 Kao Corporation Procédé de défrisage semi-permanent des cheveux et soins ultérieurs des cheveux
WO2016102206A1 (fr) * 2014-12-22 2016-06-30 Kao Germany Gmbh Procédé de traitement capillaire
JP2019123701A (ja) * 2018-01-12 2019-07-25 株式会社イングラボ 毛髪処理剤

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* Cited by examiner, † Cited by third party
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"Walter Noll's Chemistry and Technology of Silicones", 1968, ACADEMIC PRESS
COSMETICS AND TOILETRIES, vol. 91, no. 76, pages 27 - 32

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