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WO2025018433A1 - Procédé de traitement de fibres kératiniques - Google Patents

Procédé de traitement de fibres kératiniques Download PDF

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Publication number
WO2025018433A1
WO2025018433A1 PCT/JP2024/080116 JP2024080116W WO2025018433A1 WO 2025018433 A1 WO2025018433 A1 WO 2025018433A1 JP 2024080116 W JP2024080116 W JP 2024080116W WO 2025018433 A1 WO2025018433 A1 WO 2025018433A1
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WO
WIPO (PCT)
Prior art keywords
weight
composition
keratin fibers
present
compound
Prior art date
Application number
PCT/JP2024/080116
Other languages
English (en)
Inventor
Romain Flouw
Nicolas MARETS
Ayano Takeda
Tomotaka Michitsuji
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 JP2023118442A external-priority patent/JP2025015194A/ja
Priority claimed from FR2309005A external-priority patent/FR3152401A3/fr
Application filed by L'oreal filed Critical L'oreal
Publication of WO2025018433A1 publication Critical patent/WO2025018433A1/fr

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Classifications

    • 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
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • 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
    • 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
    • A61K2800/884—Sequential application

Definitions

  • the present invention mainly relates to a process for treating, preferably reshaping, and more preferably straightening, keratin fibers such as hair.
  • Reshaping 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.
  • a reshaping method using a heating iron is convenient for quick styling, it is not easy to obtain enough reshaping effect.
  • JP-A-2020-066575 discloses a hair processing method comprising: an acid treatment of applying to the hair an acidic first hair composition containing an acid and/or a salt thereof; a washing treatment of washing the hair; a silicone treatment of applying to the hair a second hair composition that is a liquid containing silicone; a drying treatment of drying the hair; and a heat treatment of bringing the hair into contact with a heating element having a preset temperature of at least 100°C.
  • US-A-2012-312317 discloses a process for semi-permanent hair straightening, comprising: a) applying a solution comprising an alpha-keto acid operable as a buffering agent; b) keeping the solution in contact with hair for 15 to 120 minutes; c) drying the hair, and d) straightening the hair with a hair straightening iron at a temperature of approximately 200 +/- 50°C.
  • JP-A-2019-123701 discloses a hair treatment method comprising:
  • a hair treatment agent to the hair, containing (a) levulinic acid of 13-30 mass% and (b) glyoxylic acid of 1-2 mass%, with the total content of levulinic acid and glyoxylic acid being 15 mass% or more and the pH ranging from 1.5 to 3.0;
  • An objective of the present invention is to provide an improved process for reshaping keratin fibers such as hair, which can provide the keratin fibers with improved reshaping effects while providing the keratin fibers with better discipline of the keratin fibers, leading to an ease of combing the keratin fibers and an ease of application of a hair iron to the keratin fibers.
  • the above objective of the present invention can be achieved by a process for reshaping, preferably straightening keratin fibers such as hair, comprising the steps of:
  • composition A comprises:
  • composition B comprises:
  • step (iii) optionally heating the keratin fibers at a temperature of more than 50°C, preferably more than 100°C, and more preferably more than 150°C, wherein the process comprises step (i) and then step (ii) or step (ii) and then step (i).
  • the (a) silicone may be selected from amino-modified silicones.
  • the amount of the (a) silicone(s) in the composition A may be from 1% to 60% by weight, preferably from 3% to 40% by weight, and more preferably from 5% to 20% by weight relative to the total weight of the composition A.
  • the plant oil may comprise at least one fatty acid.
  • the fatty acid may be selected from monounsaturated and polyunsaturated fatty acids.
  • the fatty acid may be selected from saturated fatty acids having from 8 to 28 carbon atoms.
  • the fatty acid(s) may be present in the (b) plant oil(s) in an amount of 50% by weight or more, preferably 65% by weight or more, and more preferably 80% by weight or more, relative to the total weight of the (b) plant oil(s).
  • the amount of the (b) plant oil(s) in the composition A may be from 1% to 60% by weight, preferably from 3% to 40% by weight, and more preferably from 5% to 20% by weight relative to the total weight of the composition A.
  • the total amount of the (a) silicone(s) and the (b) plant oil(s) in the composition A may be from 3% to 99% by weight, preferably from 5% to 75% by weight, and more preferably from 10% to 50% by weight relative to the total weight of the composition A.
  • the amount of the (c) compound(s) in the composition B 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 B.
  • the (d) compound may be selected from levulinic acid, a salt thereof, and a mixture thereof.
  • the amount of the (d) compound(s) in the composition B 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 B.
  • the pH of the composition B may be 7 or less, preferably 6 or less, and more preferably 5 or less.
  • the process according to the present invention may not include application of ammonia or a thiol compound onto the keratin fibers.
  • the process according to the present invention may not include application of a reducing agent or an oxidizing agent onto the keratin fibers.
  • the present invention may relate to a kit for reshaping, preferably straightening keratin fibers such as hair, comprising: a composition A comprising:
  • composition B comprising:
  • the present invention also relates to a use of a combination of a composition A and a composition B for reshaping, preferably straightening keratin fibers such as hair, wherein the composition A comprises:
  • composition B comprises:
  • composition A comprises at least one silicone and at least one plant oil
  • composition B comprises at least one glyoxylic acid or a derivative thereof and at least one keto acid or a salt thereof.
  • the present invention mainly relates to a process for reshaping, preferably straightening keratin fibers such as hair, comprising the steps of:
  • composition A comprises:
  • composition B comprises:
  • step (iii) optionally heating the keratin fibers at a temperature of more than 50°C, preferably more than 100°C, and more preferably more than 150°C, wherein the process comprises step (i) and then step (ii) or step (ii) and then step (i).
  • the present invention can improve a process for reshaping keratin fibers such as hair, with the application of two different compositions, the composition A and the composition B, by providing improved reshaping effects.
  • the process according to the present invention can provide keratin fibers such as hair, with better discipline of keratin fibers, leading to an ease of combing the keratin fibers and an ease of application of a hair iron to the keratin fibers.
  • the present invention can provide keratin fibers with less damage as compared to conventional straightening 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.
  • the present invention can use no or very little ammonia or a 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.
  • the present invention relates to a process for reshaping, preferably straitening keratin fibers, preferably hair, comprising the steps of:
  • composition A comprises:
  • composition B comprises: (c) 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; and
  • step (iii) optionally heating the keratin fibers at a temperature of more than 50°C, preferably more than 100°C, and more preferably more than 150°C, wherein the process comprises step (i) and then step (ii) or step (ii) and then step (i).
  • the process according to the present invention is for the purpose of reshaping keratin fibers such as hair, preferably reshaping for a long period of time, and more preferably reshaping even after shampooing.
  • the process according to the present invention can be a semi-permanent reshaping process.
  • the step (i) is to apply a composition A onto the keratin fibers.
  • the composition A will be described in detail later.
  • composition A may be performed by any means, such as a brush and a comb.
  • the bath ratio of the applied composition A 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 applied amount of the composition A onto the keratin fibers is not particularly limited, but in general ranges from 0.1 g to 1 g relative to 1 g of the keratin fibers.
  • the keratin fibers are 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 cleansing step is preferably carried out once before the process of the present invention is carried out.
  • the keratin fibers be left as they are for a certain amount of time; typically from 1 second to 10 minutes, preferably from 5 seconds to 5 minutes, and more preferably from 10 seconds to 3 minutes, if necessary, in order to let the composition A penetrate into the keratin fibers.
  • composition A may or may not be rinsed off from the keratin fibers after the step (i).
  • the keratin fibers are rinsed off with water to rinse the applied composition A off the keratin fibers after the step (i).
  • the step (ii) is to apply a composition B onto the keratin fibers.
  • the composition B will be described in detail later.
  • the application of the composition B may be performed by any means, such as a brush or a comb.
  • the bath ratio of the applied composition B 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, respectively.
  • 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 applied amount of the composition B onto the keratin fibers is not particularly limited, but in general ranges from 0.1 g to 1 g relative to 1 g of the keratin fibers.
  • the keratin fibers are cleaned before the step (ii).
  • 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 (ii).
  • the keratin fibers be left as they are for a certain amount of time; typically from 1 second to 30 minutes, preferably from 5 seconds to 20 minutes, and more preferably from 10 seconds to 15 minutes, if necessary, in order to let the composition B penetrate into the keratin fibers.
  • composition B may or may not be rinsed off from the keratin fibers after the step (ii).
  • the keratin fibers are rinsed off with water to rinse the applied composition B off the keratin fibers after the step (ii).
  • the process comprises the step (i) and then the step (ii) in this order.
  • the process comprises the step (ii) and then the step (i) in this order.
  • the process comprises the step (i) and then the step (ii) and then the step (i) again in this order.
  • the step (iii) is an optional step.
  • the step (iii) is to heat the keratin fibers at a temperature of more than 50°C, preferably more than 100°C, and more preferably more than 150°C.
  • the step (iii) can be carried out after the both of the steps (i) and (ii) are finished.
  • the keratin fibers are dried just before the step (iii).
  • the drying of the keratin fibers can be performed with a conventional drying means such as a hair dryer.
  • the keratin fibers which are preferably dry, are heated at a temperature of more than 50°C, preferably more than 100°C, and more preferably more than 150°C, with a heater, preferably a heating iron or a heating curler.
  • 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.
  • the heating can be carried out with conventional means, such as applying a heating iron or curler, or a dryer.
  • the reshaping may be performed by providing the keratin fibers with any mechanical force such as mechanical tension.
  • the mechanical force can be applied to the keratin fibers by any reshaping means to deform the keratin fibers to an intended shape.
  • the mechanical power may be provided by at least one reshaping means selected from the group consisting of at least one iron, at least one curler, and a combination thereof. Any conventional iron or curler may be used as the reshaping means.
  • the reshaping means may comprise at least one heater.
  • the reshaping means may be at least one heating iron and/or at least one heating curler.
  • the keratin fibers may be straightened or curled.
  • the process according to the present invention can be for straitening or curling keratin fibers, such as hair.
  • 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 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 the direction of the 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.
  • the heating time may depend on the temperature of the heating iron but also on the number of strokes of the heating iron. It may be, for example, from 1 second to 10 minutes, and preferably from a few seconds to 5 minutes.
  • 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.
  • step (iii) mechanical tension may be applied to keratin fibers as explained above.
  • compositions A and B used in the process according to the present invention will be explained.
  • composition A Composition A
  • composition A of the present invention comprises:
  • composition A 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 used for 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 A of the present invention is preferably in the form of an emulsion, and more preferably an O/W emulsion.
  • composition A used for the present invention may be in any galenical form.
  • the composition A used for the present invention may be in the form of any treatment for hair in general, such as a cream, a lotion, a gel, or the like.
  • composition A used for the present invention may have a pH of 8 or less, preferably 7 or less, and more preferably 6 or less, which is measured at 25 °C.
  • composition used for the present invention may have a pH of 3 or more, preferably 4 or more, and more preferably 4.5 or more, which is measured at 25°C.
  • composition used for the present invention may have a pH of from 3 to 8, preferably from 4 to 7, and more preferably from 4.5 to 6, which is measured at 25°C.
  • composition A The ingredients of the composition A are described in a detailed manner below.
  • composition A in the process according to the present invention comprises at least one silicone. Two or more silicones may be included in the composition A. Thus, a single type of silicone or a combination of different types of silicones may be used in the composition A.
  • the most common hydrocarbon radicals are alkyl radicals, in particular Ci-Cio alkyl radicals and especially methyl, fluoroalkyl radicals, and aryl radicals and especially phenyl.
  • the (a) silicone may be selected from silicone oils.
  • silicone oil means a silicone compound or substance which is in the form of a liquid or a paste at room temperature (25°C) under atmospheric pressure (760 mmHg).
  • silicone oils those generally used in cosmetics may be used alone or in combination.
  • Silicones or 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 silicone oil(s) may be selected from volatile silicones, non-volatile silicones and mixtures thereof.
  • the silicone oil may comprise either at least one volatile silicone oil or at least one nonvolatile silicone oil, or both at least one volatile silicone oil and at least one non-volatile silicone oil.
  • the volatile or non-volatile silicone may be selected from linear, branched, or cyclic silicones, optionally modified with at least one organo-functional moiety or group.
  • the (a) silicone is preferably non-volatile.
  • the silicone oil may be selected from the group consisting of polydialkylsiloxanes such as polydimethylsiloxanes (PDMS), polyalkylarylsiloxanes such as phenyltrimethicone, polydiarylsiloxanes, and organo-modified polysiloxanes comprising at least one organo-functional moiety or group chosen from poly(oxyalkylene) moieties or groups, alkoxy or alkoxyalkyl moieties or groups, hydroxyl or hydroxylated moieties or groups, acyloxy or acyloxyalkyl moieties or groups, carboxylic acid or carboxylate moieties or groups, acrylic moieties or groups, and oxazoline moieties.
  • PDMS polydimethylsiloxanes
  • polyalkylarylsiloxanes such as phenyltrimethicone
  • polydiarylsiloxanes polydiarylsiloxanes
  • the silicone oil(s) may be chosen from non-volatile silicones, such as polydialkylsiloxanes, polyalkylarylsiloxanes, polydiarylsiloxanes, and organo-modified polysiloxanes as explained above.
  • the molecular weight of the (a) silicone preferably polydimethylsiloxanes with trimethylsilyl end groups, has a weight-average molecular weight (Mw) of 300,000 or more, preferably 350,000 or more, more preferably 400,000 or more, and preferably 3,000,000 or less, more preferably 2,000,000 or less, even more preferably 1,000,000 or less.
  • Mw weight-average molecular weight
  • the (a) silicone preferably silicone oil
  • the (c) silicones that are preferred in accordance with the present invention may be the polydimethylsiloxanes with trimethylsilyl end groups, such as the oils having a viscosity at 25°C greater than 1,000,000 cSt (mm 2 /s), even more preferentially a viscosity greater than 2,000,000 cSt, and even more particularly greater than 5,000,000 cSt, better still greater than 10,000,000 cSt and preferably less than 50,000,000 cSt, better still less than 30,000,000 cSt, even better still less than 15,000,000 cSt.
  • all the polydimethylsiloxanes can be used as they are or in the form of solutions, emulsions, nanoemulsions or microemulsions.
  • Non-limiting examples of commercial products corresponding to such polydialkylsiloxanes include BY22-029 (product of Dow Corning Toray, Co., Ltd.; nonionic emulsion of dimethicone oil), BY22-060 (product of Dow Corning Toray, Co., Ltd.; cationic emulsion containing a solution obtained by diluting highly polymerized dimethicone with a low viscosity silicone), BY22-019 (product of Dow Coming Toray, Co., Ltd.; nonionic and cationic emulsion containing a solution obtained by diluting highly polymerized dimethicone with cyclic silicone), BY22-020 (product of Dow Corning Toray, Co., Ltd.; cationic emulsion containing a solution obtained by diluting a highly polymerized dimethicone with light liquid isoparaffin), KM902 (product of Shin-Etsu Chemical Co., Ltd.; nonionic emulsion of highly polymer
  • Polyalkylarylsiloxanes may be chosen from polydimethyl/methylphenylsiloxanes and linear and/or branched polydimethyl/diphenyl siloxanes.
  • 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; and some SF series fluids from GENERAL ELECTRIC, such as SF 1023, SF 1154, SF 1250, and SF 1265.
  • Organo-modified 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 organo-functional moiety or group linked directly or by means of a hydrocarbon group.
  • Organo-modified silicones may include, for example, polyorganosiloxanes comprising: polyethyleneoxy and/or polypropyleneoxy moieties optionally comprising C6-C24 alkyl moieties, such as products called dimethicone copolyols marketed by DOW CORNING under the trade name DC 1248 and under the trade name DC Q2-5220 and SILWET® L 722, L 7500, L 77, and L 711 fluids marketed by UNION CARBIDE and (Ci2)alkyl-methicone copolyol marketed by DOW CORNING under the trade name Q2 5200; 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
  • 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.
  • 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
  • the silicone oil(s) may be chosen from polydimethylsiloxanes and organo -modified polydimethylsiloxanes. It is preferable that the silicone oil be selected from volatile or non-volatile silicone oils, such as volatile or non-volatile polydimethylsiloxanes (PDMS) containing a linear or cyclic silicone chain, that are liquid or pasty at ambient temperature, in particular cyclopolydimethylsiloxanes (cyclomethicones) such as cyclopentasiloxane and cyclohexasiloxane; polydimethylsiloxanes containing alkyl, alkoxy, or phenyl groups that are pendent and/or at the end(s) of the silicone chain, which groups have from 2 to 24 carbon atoms; phenyl silicones such as phenyltrimethicones, phenyldimethicones, phenyltrimethyls
  • PDMS volatile or non-volatile polydi
  • Non-limiting examples of such combinations include a mixture of cyclopentasiloxane and dimethiconol, marketed, for instance, under the trade name Xiameter PMX-1501 Fluid by Dow Corning.
  • the degree of polymerization of the (a) silicone be less than 2,000, more preferably less than 1,500, and even more preferably less than 1,000.
  • the (a) silicone is selected from amino-modified silicones.
  • amino-modified silicone denotes any silicone comprising at least one primary, secondary or tertiary amine or one quaternary ammonium, and more particularly at least one primary amine.
  • aminosilicone that may be used in the present invention, the following can be cited:
  • G independently designates a hydrogen atom, or a phenyl, OH, or a C 1 -C 8 alkyl group, for example methyl, or a C 1 -C 8 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 less than 2,000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to less than 1,999 and in particular from 49 to 149, and for m to denote a number from 1 to less than 2,000 and in particular from 1 to 10;
  • R' independently denotes a monovalent group having formula -C q H 2q L in which q is a number ranging from 2 to 8 and L is an optionally quaternized amino group chosen from the following groups:
  • R" independently denotes hydrogen, phenyl, benzyl, or a saturated monovalent hydrocarbonbased group, for example a C 1 -C 20 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; and
  • 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.
  • n and n are numbers such that the sum (n + m) can range from 1 to 1,000, in particular from 50 to 250 and more particularly from 100 to 200, it being possible for n to denote a number from 0 to 999 and in particular from 49 to 249, and more particularly from 125 to 175, and for m to denote a number from 1 to 1,000 and in particular from 1 to 10, and more particularly from 1 to 5;
  • R 1 , R 2 , and R 3 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 silicone ranges preferably from 2,000 to 230,000, more particularly from 3,500 to 150,000.
  • 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 R 1 or R 2 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 silicone ranges preferably from 2,000 to 200,000, even more particularly 5,000 to 100,000 and more particularly from 10,000 to 50,000.
  • Commercial products corresponding to these 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 aminosilicone having structure (D) is sold by Wacker under the name BELSIL ADM 652.
  • a product containing 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 less than 2,000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to less than 1 ,999 and in particular from 49 to 149, and for m to denote a number from 1 to less than 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 these aminosilicones 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 trade name XIAMETER® MEM-8299 Cationic Emulsion by Dow Coming.
  • 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 less than 2,000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to less than 1,999 and in particular from 49 to 149, and for m to denote a number from 1 to less than 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 these aminosilicones 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 DC2-8566 Amino Fluid by Dow Coming.
  • R 5 independently represents a monovalent hydrocarbon-based group containing from 1 to 18 carbon atoms, and in particular a C 1 -C 18 alkyl or C 2 -C 18 alkenyl group, for example methyl;
  • R 6 represents a divalent hydrocarbon-based group, in particular a C 1 -C 18 alkylene group or a divalent C 1 -C 18 , for example C 1 -C 8 , alkyleneoxy group linked to 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; and s represents a mean statistical value from 20 to 200 and in particular from 20 to 50.
  • R 7 independently represents a monovalent hydrocarbon-based group containing from 1 to 18 carbon atoms, and in particular a C 1 -C 18 alkyl group, a C 2 -C 18 alkenyl group or a ring containing 5 or 6 carbon atoms, for example methyl;
  • Re independently represents a divalent hydrocarbon-based group, in particular a Ci- C 18 alkylene group or a divalent C 1 -C 18 , for example C 1 -C 8 , alkyleneoxy group linked to the Si via an SiC bond;
  • R 8 independently represents a hydrogen atom, a monovalent hydrocarbon-based group containing from 1 to 18 carbon atoms, and in particular a C 1 -C 18 alkyl group, a C 2 -C 18 alkenyl group or a -R 6 -NHCOR 7 group;
  • X- is an anion such as a halide ion, in particular chloride, or an organic acid salt (for example acetate); and r represents a mean statistical value from 2 to 200 and in particular from 5 to 100.
  • R 1 , R 2 , R 3 and R4 independently denote a C 1 -C 4 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:
  • 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 C 2 -C 12 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 CH 2 CH 2 OCH(OH)CH 2 - group; preferentially R independently denotes a -CH 2 CH 2 CH 2 OCH(OH)CH2- group; and
  • R' independently represents a divalent linear or branched C 2 -C 12 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 CH 2 CH 2 OCH(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 copolymer in a 30% solution in dipropylene glycol, more particularly between 0.05 and 0.2.
  • the weight-average molecular weight (Mw) of the silicone is preferably between 5,000 and 1,000,000, more particularly between 10,000 and 200,000.
  • R, R' and R" independently represent a C 1 -C 4 alkyl or hydroxy group
  • A represents a C 3 alkylene group and m and n are such that the sum of m + n is less than 2,000, preferably less than 1,500, and more preferably less than 1,000 approximately; in which: x and y are numbers such that the sum of x and y ranges from 1 to less than 2,000; preferably, x ranges from 10 to less than 1,500 and especially from 100 to 1,000; preferably, y ranges from 1 to 100;
  • R1 and R2 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; and
  • 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: CH2CH2CH2- and - CH 2 CH(CH 3 )CH 2 -; and
  • R1 and R2 being independently linear, saturated alkyl groups comprising 6 to 30 carbon atoms, preferably 8 to 24 carbon atoms and especially 12 to 20 carbon atoms; chosen in particular from dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl groups; preferentially, R1 and R2, which may be identical or different, being chosen from hexadecyl (cetyl) and octadecyl (stearyl) groups.
  • a preferred silicone of formula (K) is bis-cetearyl amodimethicone.
  • aminosilicones of the present disclosure may also be chosen from polydimethylsiloxanes comprising primary amine groups at the chain end or on side chains, for example aminopropyl end or side groups, for instance those of formula (A), (B), or (C):
  • n is less than 2,000, preferably less than 1,500, and more preferably less than 1,000.
  • aminosilicone (A) mention may be made of those sold under the names DMS-A11, DMS-A12, DMS-A15, DMS-A21, DMS-A31, DMS- A32 and DMS-A35 by the company Gelest.
  • n and m are such that it is less than 2,000, preferably less than 1,500, and more preferably less than 1,000.
  • 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.
  • n is less than 2,000, preferably less than 1,500, and more preferably less than 1,000.
  • silicone (C) mention may be made of those sold under the names MCR-A11 and MCR-A12 by the company Gelest.
  • the aminosilicone according to the present invention is amodimethicone.
  • the aminosilicone is bis-cetearyl amodimethicone.
  • the aminosilicone is aminopropyl dimethicone.
  • 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 10 -6 to 2.5 m 2 /s at 25°C, for example, from 1 ⁇ 10 -5 to 1 m 2 /s.
  • the silicone(s) used in the present invention can also be a silicone gum.
  • silicone gum used herein means polyorganosiloxanes with a weight-average molecular weight (Mw) of between 200,000 and 2,000,000 used alone or as a mixture in a solvent chosen from volatile silicones, polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffins, methylene chloride, pentane or mixtures thereof; they can, for example, have one of the following structures: poly dimethylsiloxane, poly [(dimethylsiloxane) I (methyl vinylsiloxane)], poly [(dimethylsiloxane) I (vinylhydrogenosiloxane)], poly[(dihydrogenodimethylsiloxane) / (di vinylsiloxane)], poly[(dimethylsiloxane) / (diphenylsiloxane)
  • the silicones can be used as they are or in the form of solutions in organic solvents or else in the form of emulsions or microemulsions.
  • the silicone is in the form of an aqueous emulsion.
  • aqueous emulsion is intended to mean an emulsion of oil-in- water type in which the silicone copolymer is dispersed in the form of particles or droplets in the aqueous phase forming the continuous phase of the emulsion.
  • This silicone emulsion can have a silicone droplet or particle size ranging from 10 nm to 50 pm, and preferably from 0.3 pm to 20 pm. The particle size is measured by laser particle sizing.
  • This emulsion can be stabilized with a customary emulsifying system.
  • the emulsifying system comprises surfactants that are normally used in silicone emulsions. These surfactants may be nonionic, cationic, anionic or amphoteric surfactants or mixtures thereof.
  • the (a) silicone(s) may be present in an amount of 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 A.
  • the (a) silicone(s) may be present in an amount of 60% by weight or less, preferably 40% by weight or less, and more preferably 20% by weight or less, relative to the total weight of the composition A.
  • the amount of (a) silicone(s) in the composition A according to the present invention may be from 1% to 60% by weight, preferably from 3% to 40% by weight, and more preferably from 5% to 20% by weight relative to the total weight of the composition A.
  • composition A according to the present invention comprises (b) at least one plant oil.
  • Two or more (b) plant oils may be used in combination.
  • a single type of (b) plant oil or a combination of different types of (b) plant oils may be used.
  • oils means a fatty compound or substance which is in the form of a liquid or a paste (non-solid) at room temperature (25°C) under atmospheric pressure (760 mmHg). These oils may be volatile or non-volatile, polar or apolar, and preferably non-volatile and polar.
  • polar oil is intended to mean an oil of which the solubility parameter ⁇ a at 25°C is other than 0 (J/cm 3 ) 1/2 .
  • polar oil is intended to mean an oil of which the chemical structure is formed essentially from, or even constituted of, carbon and hydrogen atoms, and comprising at least one highly electronegative heteroatom such as an oxygen, nitrogen, silicon or phosphorus atom.
  • ⁇ a ( ⁇ P 2 + ⁇ h 2 ) 1/2 .
  • ⁇ P , ⁇ h , ⁇ D and ⁇ a are expressed as (J/cm 3 ) 1/2 .
  • plant oil here means oils of plant origin.
  • the plant oil can be hydrocarbon-based oils.
  • hydrocarbon-based oil or “hydrocarbon oil” is intended to mean an oil mainly containing hydrogen and carbon atoms and optionally oxygen, nitrogen, sulfur and/or phosphorus atoms.
  • the hydrocarbon-based oil does not comprise any silicon atoms.
  • Examples of the (b) plant oils may include, but are not limited to, shea oil, alfalfa oil, poppy oil, winter squash oil, millet oil, barley oil, quinoa oil, rye oil, candlenut oil, passionflower oil, aloe vera oil, sweet almond oil, peach stone oil, groundnut oil, argan oil, avocado oil, baobab oil, borage oil, broccoli oil, calendula oil, camelina oil, canola oil, carrot oil, safflower oil, flax oil, rapeseed oil, cotton oil, coconut oil (cocos nucifera oil), marrow seed oil, wheatgerm oil, jojoba oil, lily oil, macadamia oil, corn oil, meadowfoam oil, St John's Wort oil, monoi oil, hazelnut oil, apricot kernel oil, walnut oil, olive oil, evening primrose oil, palm oil, blackcurrant pip oil, kiwi seed oil, grapeseed oil, pistachio
  • the (b) plant oil may include at least one fatty acid.
  • the (b) plant oil can be fatty-acid blend plant oils.
  • the (b) plant oil may include a single type of fatty acid or a combination of different types of fatty acids.
  • fatty acid here means a monofunctional carboxylic acid with an aliphatic chain.
  • the fatty acid may be linear or branched. In one preferred embodiment of the present invention, the fatty acid is linear.
  • the fatty acid may be saturated or unsaturated. In one embodiment of the present invention, the fatty acid is selected from saturated fatty acids. In another embodiment of the present invention, the fatty acid is selected from unsaturated fatty acids. The fatty acid may be selected from monounsaturated and polyunsaturated fatty acids. The fatty acid may be selected from monounsaturated and polyunsaturated fatty acids having 1 to 3 carbon-carbon double bonds, and more preferably monounsaturated fatty acids.
  • Non-limiting examples of the fatty acid include fatty acids having from 8 to 28 carbon atoms, preferably from 10 to 24 carbon atoms, and more preferably from 12 to 22 carbon atoms.
  • the fatty acid is selected from linear saturated fatty acids and linear unsaturated fatty acids having 1 to 3 carbon-carbon double bonds, preferably monounsaturated fatty acids.
  • the fatty acid is selected from linear fatty acids having from 8 to 28 carbon atoms, preferably from 10 to 24 carbon atoms, and more preferably from 12 to 22 carbon atoms, wherein the fatty acids are saturated or monounsaturated.
  • the fatty acid can be represented by the following formula (I):
  • R is a linear or branched, preferably linear, C8-C28 alkyl or alkenyl group, preferably a C10-C24 alkyl or alkenyl group, more preferably a C12-C22 alkyl group or alkenyl group.
  • R may comprise 1 to 3 carbon-carbon double bonds, and preferably a carbon-carbon double bond.
  • fatty acids mention can be made of arachidic acid, capric acid, caprylic acid, lauric acid, linoleic acid, linolenic acid, myristic acid, oleic acid, palmitic acid, palmitoleic acid, stearic acid, eicosenoic acid, erucic acid, and mixtures thereof.
  • the fatty acid is selected from linoleic acid, linolenic acid, oleic acid, palmitoleic acid, eicosenoic acid, erucic acid, and mixtures thereof.
  • the (b) plant oil is selected from avocado oil, jojoba oil, and a combination thereof.
  • the fatty acid(s) may be present in the (b) plant oil(s) in an amount of 50% by weight or more, preferably 65% by weight or more, and more preferably 80% by weight or more, relative to the total weight of the (b) plant oil(s).
  • the (b) plant oil comprises at least one monounsaturated fatty acid, and preferably at least one linear monounsaturated fatty acid, having from 8 to 28 carbon atoms, preferably from 10 to 24 carbon atoms, and more preferably from 12 to 22 carbon atoms.
  • the monosaturated fatty acid(s) may be present in the (b) plant oil(s) in an amount of 50% by weight or more, preferably 60% by weight or more, and more preferably 70% by weight or more, relative to the total weight of the (b) plant oil(s).
  • the linear monosaturated fatty acid(s) may be present in the (b) plant oil(s) in an amount of 50% by weight or more, preferably 60% by weight or more, and more preferably 70% by weight or more, relative to the total weight of the (b) plant oil(s).
  • the (b) plant oil(s) may be present in an amount of 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 A.
  • the (b) plant oil(s) may be present in an amount of 60% by weight or less, preferably 40% by weight or less, and more preferably 20% by weight or less, relative to the total weight of the composition A.
  • the amount of the (b) plant oil(s) in the composition A according to the present invention may be from 1% to 60% by weight, preferably from 3% to 40% by weight, and more preferably from 5% to 20% by weight relative to the total weight of the composition A,
  • the total amount of the (a) silicone(s) and the (b) plant oil(s) in the composition A may be 3% by weight or more, preferably 5% by weight or more, and more preferably 10% by weight or more, relative to the total weight of the composition A.
  • the total amount of the (a) silicone(s) and the (b) plant oil(s) in the composition A may be 99% by weight or less, preferably 75% by weight or less, and more preferably 50% by weight or less, relative to the total weight of the composition A.
  • the total amount of the (a) silicone(s) and the (b) plant oil(s) in the composition A may be from 3% to 99% by weight, preferably from 5% to 75% by weight, and more preferably from 10% to 50% by weight relative to the total weight of the composition A.
  • composition B of the present invention comprises:
  • composition B 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 used for 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 B of the present invention is preferably in the form of an emulsion, and more preferably an O/W emulsion.
  • composition B used for the present invention may be in any galenical form.
  • the compositions used for the present invention may be in the form of any treatment for hair in general, such as a cream, a lotion, a gel, or the like.
  • composition B used for 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 B used for the present invention may have a pH of 3 or more, which is measured at 25°C.
  • composition B used for 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 B The ingredients of the composition B are described in a detailed manner below.
  • composition B comprises (c) 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 (c) compound may be used, or two or more different types of (c) compounds may be used in combination.
  • the (c) 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 (c) 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.
  • the amount of the (c) 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 (c) compound(s) in the composition according to the present invention is less than 25% by weight, preferably less than 20% by weight, and more preferably less than 15% by weight, relative to the total weight of the composition B.
  • the amount of the (c) compound(s) in the composition according to the present invention may be from 0.1% to less than 25% by weight, preferably from 0.5% to less than 20% by weight, and more preferably from 1% to less than 15% by weight, relative to the total weight of the composition B.
  • the amount of the (c) compound(s) in the composition according to the present invention may be more than 3% by weight, preferably more than 5% by weight, and more preferably more than 10% by weight, relative to the total weight of the composition B.
  • the amount of the (c) compound(s) in the composition according to the present invention may be more than 3% and less than 25% by weight, preferably more than 5% and less than 20% by weight, and more preferably more than 10% and less than 15% by weight, relative to the total weight of the composition.
  • composition according to the present invention comprises (d) at least one compound, different from the (c) compound, selected from keto acids, salts thereof, and mixtures thereof.
  • Two or more (d) compounds may be used in combination.
  • a single type of (d) compound or a combination of different types of (d) compounds may be used.
  • the keto acids may be selected from a-keto acids, [3-keto acids, y-keto acids, and mixtures thereof.
  • the a-keto acids may be compounds represented by the general formula (I):
  • R 1 denotes a linear or branched Cj-Cg alkyl group, optionally substituted with an OH, COOH or a halogen atom such as a chlorine or bromine atom.
  • a-keto acids include pyruvic acid.
  • the ⁇ -keto acids may be represented by the general formula (II):
  • 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.
  • ⁇ -keto acids include acetoacetic acid.
  • the y-keto acids may be represented by the general formula (III):
  • R 2 denotes a linear or branched C 1 -C 6 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.
  • (d) compound(s) "/-keto acid, and more preferably levulinic acid and/or a salt thereof such as sodium levulinate.
  • the amount of the (d) compound(s) in the composition B of 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 B.
  • the amount of the (d) compound(s) in the composition B of the present invention is 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 B.
  • the amount of the (d) compound(s) in the composition B of 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 B.
  • the amount of the (d) compound(s) in the composition B of 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 B.
  • the amount of the (d) compound(s) in the composition B of 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 amount of the (d) compound(s) in the composition B of the present invention may be from 0.5% to 10% by weight, preferably from 1% to 5% by weight, and more preferably from 2% to 4% by weight, relative to the total weight of the composition B.
  • the (c) compound(s) is (are) present in a less amount than the (b) compound(s) in the composition B.
  • the weight ratio of the (b) compound(s) to the (c) compound(s) included in the composition B may range from 1 :1 to 10:1, preferably from 1.5:1 to 7:1, and more preferably from 2:1 to 5:1.
  • compositions A and B according to the present invention may comprise water, respectively.
  • compositions A and B according to the present invention comprises water
  • the compositions according to the present invention are not anhydrous.
  • the amount of water in the each of compositions A and B 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 each of the compositions.
  • the amount of water in each of the compositions A and B according to the present invention may be 95% by weight or less, preferably 90% by weight or less, and more preferably 85% by weight or less relative to the total weight of each of the compositions.
  • the amount of water in each of the compositions 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 each of the compositions.
  • compositions A and B according to the present invention may or may not 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 composition A does not comprise any alkaline agent, while the composition B comprises at least one alkaline agent.
  • 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-m ethyl- 1,3 -propanediol, 3 -amino- 1,2- 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 each of the compositions A and B 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 each of the compositions.
  • the amount of the alkaline agent(s) in each of the compositions A and B 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 each of the compositions.
  • 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 each of the compositions.
  • compositions A and B of the present invention may or may not comprise at least one oil other than the (b) plant oil.
  • Two or more oils may be used in combination.
  • a single type of oil or a combination of different types of oils may be used.
  • each of the compositions A and B of the present invention comprise at least one oil other than the (b) plant oil.
  • 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 oil may be a non-polar oil such as a hydrocarbon oil, or the like; a polar oil such as an animal oil and an ester oil or an ether oil; or a mixture thereof.
  • the oil may be selected from the group consisting of oils of animal origin, synthetic 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 palmito stearate 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.
  • Glucate® DO is sold under the name Glucate® DO by the company Amerchol, which is a methylglucose dioleate.
  • 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/ capryl ate/linolenate) .
  • capryl caprylyl glycerides glyceryl trimyristate, glyceryl tripalmitate, glyceryl trilinolenate, glyceryl trilaurate, glyceryl tricaprate, glyceryl tricaprylate, glyceryl tri(caprate/caprylate) and glyceryl tri (caprate/ capryl ate/linolenate) .
  • Hydrocarbon oils may be chosen from: linear or branched, optionally cyclic, C 6 -C 16 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.
  • hydrocarbon oils As preferable examples of hydrocarbon oils, mention may be made of, for example, linear or branched hydrocarbons such as isohexadecane, isododecane, squalane, mineral oil (e.g., liquid paraffin), paraffin, vaseline or petrolatum, naphthalenes, and the like; hydrogenated polyisobutene, isoeicosan, and decene/butene copolymers; and mixtures thereof.
  • linear or branched hydrocarbons such as isohexadecane, isododecane, squalane, mineral oil (e.g., liquid paraffin), paraffin, vaseline or petrolatum, naphthalenes, and the like; hydrogenated polyisobutene, isoeicosan, and decene/butene copolymers; and mixtures thereof.
  • the oil be chosen from polar oils, more preferably ester oils, and even more preferably monoester oils.
  • the amount of the oil(s) in each of the compositions A and B of 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 each of the compositions.
  • the amount of the oil(s) in each of the compositions A and B of according to the present invention may be 20% by weight or less, preferably 15% by weight or less, and more preferably 10% by weight or less, relative to the total weight of each of the compositions.
  • the amount of the oil(s) in each of the compositions A and B of the present invention may be from 0.1% to 20% by weight, preferably from 0.5% to 15% by weight, and more preferably from 1% to 10% by weight, relative to the total weight of each of the compositions.
  • compositions A and B of the present invention may or may not comprise 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.
  • compositions B of the present invention comprises at least one fatty alcohol, but the composition A does not comprise the fatty alcohol.
  • 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 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 may represent a mixture of fatty alcohols, which means that several species of fatty alcohols may coexist, in the form of a mixture, in a commercial product.
  • 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 fatty alcohol(s) in each of the compositions A and B of the present invention may be 0.5% by weight or more, preferably 1% by weight or more, and more preferably 2% by weight or more, relative to the total weight of each of the compositions.
  • the amount of the fatty alcohol(s) in each of the compositions A and B of according to the present invention may be 20% by weight or less, preferably 15% by weight or less, and more preferably 10% by weight or less, relative to the total weight of each of the compositions.
  • the amount of the fatty alcohol(s) in each of the compositions A and B of the present invention may be from 0.5% to 20% by weight, preferably from 1% to 15% by weight, and more preferably from 2% to 10% by weight, relative to the total weight of each of the compositions.
  • compositions A and B of the present invention may or may not comprise at least one nonionic surfactant.
  • a single type of nonionic surfactant may be used, or two or more different types of nonionic surfactants may be used in combination.
  • each of the compositions A and B of the present invention comprises at least one nonionic surfactant.
  • nonionic surfactants are compounds well known in and of themselves (see, e.g., in this regard, "Elandbook of Surfactants” by M. R. Porter, Blackie & Son publishers (Glasgow and London), 1991, pp. 116-178).
  • they can, for example, be chosen from alcohols, alphadiols, alkylphenols, and esters of fatty acids, these compounds being ethoxylated, propoxylated, or glycerolated and having at least one fatty chain comprising, for example, from 8 to 30 carbon atoms, it being possible for the number of ethylene oxide or propylene oxide groups to range from 2 to 50, and for the number of glycerol groups to range from 1 to 30.
  • Maltose derivatives may also be mentioned. Non-limiting mention may also be made of copolymers of ethylene oxide and/or of propylene oxide; condensates of ethylene oxide and/or of propylene oxide with fatty alcohols; polyethoxylated fatty amides comprising, for example, from 2 to 30 mol of ethylene oxide; polyglycerolated fatty amides comprising, for example, from 1.5 to 5 glycerol groups, such as from 1.5 to 4; ethoxylated fatty acid esters of sorbitan comprising from 2 to 30 mol of ethylene oxide; ethoxylated oils of plant origin; fatty acid esters of sucrose; fatty acid esters of polyethylene glycol; polyethoxylated fatty acid mono or diesters of glycerol (C 6 -C 24 )alkylpolyglycosides; N-(C 6 -C 24 )alkylglucamine derivatives; amine oxides such as (C 10 -C
  • the nonionic surfactants may preferably be chosen from monooxyalkylenated, polyoxyalkylenated, monoglycerolated, or polyglycerolated nonionic surfactants.
  • the oxyalkylene units are more particularly oxyethylene or oxypropylene units, or a combination thereof, and are preferably oxyethylene units.
  • monooxyalkylenated or polyoxyalkylenated nonionic surfactants examples include: monooxyalkylenated or polyoxyalkylenated (C 8 -C 24 )alkylphenols, saturated or unsaturated, linear or branched, monooxyalkylenated or polyoxyalkylenated CR- C 30 alcohols, saturated or unsaturated, linear or branched, monooxyalkylenated or polyoxyalkylenated CR- C 30 amides, esters of saturated or unsaturated, linear or branched, C8-C30 acids and of monoalkyleneglycol or polyalkyleneglycols, monooxyalkylenated or polyoxyalkylenated esters of saturated or unsaturated, linear or branched, C 8 -C 30 acids, and of sorbitol, saturated or unsaturated, monooxyalkylenated or polyoxyalkylenated plant oils, and condensates of ethylene oxide and/or of propy
  • the surfactants preferably contain a number of moles of ethylene oxide and/or of propylene oxide of between 1 and 100, preferably between 1 and 50, and more preferably between 1 and 20.
  • the monooxyalkylenated nonionic surfactants may be chosen from monooxyethylenated fatty alcohol (ether of ethyleneglycol and fatty alcohol), monooxyethylenated fatty ester (ester of ethyleneglycol and fatty acid), and mixtures thereof.
  • Examples of monooxyalkylenated fatty esters that may be mentioned include glycol distearate.
  • the polyoxyalkylenated nonionic surfactants may be chosen from polyoxyethylenated fatty alcohol (ether of polyethyleneglycol and fatty alcohol), polyoxyethylenated fatty ester (ester of polyethyleneglycol and fatty acid), and mixtures thereof.
  • polyoxyethylenated saturated fatty alcohols examples include adducts of ethylene oxide with lauryl alcohol, especially those containing from 2 to 20 oxyethylene units and more particularly those containing from 2 to 10 oxyethylene units (Laureth-2 to Laureth-20, as the CTFA names); adducts of ethylene oxide with behenyl alcohol, especially those containing from 2 to 20 oxyethylene units (Beheneth-2 to Beheneth-20, as the CTFA names); adducts of ethylene oxide with cetearyl alcohol (mixture of cetyl alcohol and stearyl alcohol), especially those containing from 2 to 20 oxyethylene units (Ceteareth-2 to Ceteareth-20, as the CTFA names); adducts of ethylene oxide with cetyl alcohol, especially those containing from 2 to 20 oxyethylene units (Ceteth-2 to Ceteth-20, as the CTFA names); adducts of ethylene oxide with steryl alcohol, especially those containing from 2 to 20 oxyethylene
  • polyoxyethylenated unsaturated fatty alcohols examples include adducts of ethylene oxide with oleyl alcohol, especially those containing from 2 to 20 oxyethylene units and more particularly those containing from 2 to 10 oxyethylene units (Oleth-2 to Oleth-20, as the CTFA names); and mixtures thereof.
  • nonionic surfactant be selected from monooxyalkylenated, polyoxyalkylenated nonionic surfactants, more preferably polyoxyalkylenated nonionic surfactants, and even more preferably polyoxyethylenated fatty alcohols.
  • the amount of the nonionic surfactant(s) in each of the compositions A and B of the present invention may be 0.1% by weight or more, preferably 0.25% by weight or more, and more preferably 0.5% by weight or more, relative to the total weight of each of the compositions.
  • the amount of the nonionic surfactant(s) in each of the compositions A and B of according to the present invention may be 20% by weight or less, preferably 15% by weight or less, and more preferably 10% by weight or less, relative to the total weight of each of the compositions.
  • the amount of the nonionic surfactant(s) in each of the compositions A and B of the present invention may be from 0.1% to 20% by weight, preferably from 0.25% to 15% by weight, and more preferably from 0.5% to 10% by weight, relative to the total weight of each of the compositions.
  • composition A and B of the present invention may or may not comprise at least one polyol, A single type of polyol may be used, or two or more different types of polyols may be used in combination.
  • both of the compositions A and B comprise at least one polyol.
  • polyol should be understood as meaning any organic molecule comprising at least two free hydroxyl groups.
  • the polyol that is suitable for use in the invention may be a compound of linear, branched or cyclic, saturated or unsaturated alkyl type, bearing at least two -OH functions on the alkyl chain.
  • the polyol is a compound of linear or branched, preferably linear alkyl type bearing at least two -OH functions, preferably 2 to 5 -OH functions, more preferably 2 to 4 - OH functions, and even more preferably 2 or 3 -OH functions on the alkyl chain.
  • the polyols that are advantageously suitable are those especially having from 2 to 8 carbon atoms or for example, 3 to 6 carbon atoms.
  • the polyols may be chosen from linear or branched, preferably linear polyols having from 3 to 8 carbon atoms; mention may be made especially of:
  • - diols such as hexylene glycol, dipropylene glycol, pentylene glycol, propylene glycol and butylene glycol;
  • triols such as glycerol (glycerin), and mixtures thereof.
  • the polyol is selected from linear alkyl type polyols having 3 to 6 carbon atoms.
  • the polyol(s) may be present in each of the compositions A and B of the present invention in an amount of 0.5% by weight or more, preferably 1% by weight or more, and more preferably 2% by weight or more, relative to the total weight of the composition.
  • the polyol(s) may be present in each of the compositions A and B of the present invention in an amount of 20% by weight or less, preferably 15% by weight or less, and more preferably 10% by weight or less, relative to the total weight of the composition.
  • the amount of the polyol(s) in each of the compositions A and B of the present invention may be from 0.5% to 20% by weight, preferably from 1% to 15% by weight, and more preferably from 2% to 10% by weight relative to the total weight of the composition.
  • composition A and B of the present invention may or may not comprise at least one monoalcohol.
  • a single type of monoalcohol may be used, or two or more different types of monoalcohols may be used in combination.
  • both of the compositions A and B of the present invention comprises at least one monoalcohol.
  • the monoalcohol here may be a water-soluble, hydrophilic monoalcohol.
  • hydrophilic here means that a substance is soluble in water at a concentration of at least 1% by weight relative to the total weight of water at room temperature (25°C) and atmospheric pressure (10 5 Pa).
  • the monoalcohol may be a linear or branched, saturated or unsaturated monoalcohol having from 1 to 8 carbon atoms, preferably from 2 to 8 carbon atoms, bearing only one hydroxyl (OH) function.
  • the monoalcohol may be an aliphatic monoalcohol having from 1 to 8 carbon atoms, preferably from 2 to 8 carbon atoms.
  • aliphatic monoalcohol here means any linear or branched, saturated alkane compound bearing only one hydroxyl (OH) function.
  • the aliphatic monoalcohol(s) may be chosen from ethanol, propanol, butanol, isopropanol, isobutanol and mixtures thereof.
  • the monoalcohol can be selected from linear aliphatic monoalcohols having from 1 to 8 carbon atoms, preferably from 2 to 8 carbon atoms, such as ethanol, propanol, butanol, and mixtures thereof.
  • the amount of the monoalcohol(s) in each of the compositions A and B of the present invention may be 0.1% by weight or more, preferably 0.2% by weight or more, and more preferably 0.25% by weight or more, relative to the total weight of each of the compositions.
  • the amount of the monoalcohol(s) in each of the compositions A and B of according to the present invention may be 25% by weight or less, preferably 20% by weight or less, and more preferably 15% by weight or less, relative to the total weight of each of the compositions.
  • the amount of the monoalcohol(s) in each of the compositions A and B of the present invention may be from 0.1% to 25% by weight, preferably from 0.2% to 20% by weight, and more preferably from 0.25% to 15% by weight, relative to the total weight of each of the compositions.
  • compositions A and B according to the present invention may also comprise at least one other optional ingredient, chosen in particular from: viscosity adjusters, such as thickeners; sunscreens; moisturizers; antidandruff agents; antioxidants; antibacterial agents; preservatives; 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 and amphoteric surfactants.
  • the composition can, of course, comprise several cosmetic ingredients appearing in the above list.
  • 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 in each of the compositions A and B. 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.
  • each of the compositions A and B be free of ammonia or a thiol compound.
  • free of ammonia or a thiol compound means that the composition according to the present invention does not include a substantial amount of ammonia or a thiol compound.
  • each of the compositions A and B of 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 a thiol compound, in particular no ammonia or a 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; mono- thioglycerol and derivatives thereof, in particular esters; cysteine and derivatives thereof, in particular esters such as N-acetylcysteine, N-alkanoylcysteine and cysteine al
  • 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.
  • thiol reducing agent examples include, but are not limited to, sugar N-mercapto alkyl amides such as N-(mercapto-2-ethyl)gluconamide, P-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 described in European Patent Application No. 0 368 763; aminomercapto alkyl amides such as those described in European Patent Application No.
  • alkylaminomercaptoalkylamides such as those described in European Patent Application No. 0 514 282; (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.
  • each of the compositions A and B be free of a reducing agent or an oxidizing agent.
  • free of a reducing agent or an oxidizing agent means that a composition does not include a substantial amount of a reducing agent or an oxidizing agent.
  • each of the compositions A and B of 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.
  • the oxidizing agent may be chosen from hydrogen peroxide, alkali metal bromates, ferricyanides peroxygenated salts, and compounds capable of producing hydrogen peroxide by hydrolysis.
  • the oxidizing agent can be chosen from aqueous hydrogen peroxide solution, urea peroxide, alkali metal bromates and persalts such as perborates and persulphates.
  • the process according to the present invention may or may not comprise additional step (iv) for applying at least one treatment composition other than the composition A and the composition B onto the keratin fibers.
  • additional step (iv) for applying at least one treatment composition other than the composition A and the composition B onto the keratin fibers will be described in detail later.
  • the application of the treatment composition may be performed by any means, such as a brush and a comb.
  • the process according to the present invention may comprise the step (iv) after both of the compositions A and B are applied and before the step (iii) if present.
  • the process according to the present invention may comprise the step (iv) after both of the steps (i) and (ii) are finished and before the step (iii) if present.
  • the process according to the present invention comprises step (i), step (ii), step (iv), and step (iii) in this order.
  • the process according to the present invention comprises step (ii), step (i), step (iv), and step (iii) in this order.
  • the process according to the present invention may comprise an optional step of rinsing off the keratin fibers with or without drying the keratin fibers just before and/or after the step (iv).
  • 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 applied amount of the treatment composition onto the keratin fibers is not particularly limited, but in general ranges from 0.01 g to 0,5 g relative to 1 g of the keratin fibers.
  • the process according to the present invention may comprise the step (iv) one time, or may comprise the step (iv) twice or more. In one preferred embodiment, the process according to the present invention may comprise the step (iv) twice.
  • each step (iv) can include application of the same or different treatment compositions.
  • the process comprises step (iv) twice, and each step (iv) includes the application of a different composition onto the keratin fibers.
  • the process according to the present invention does not comprise a rinsing step after the step (iv).
  • the treatment composition used in the step (iv) can be a leave-on type cosmetic composition.
  • the form of the treatment composition which can be 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 used for 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.
  • the treatment compositions which can be used for the present invention may have a pH of from 3 to 8, preferably from 3 to 7 at 25 °C.
  • the formulations of the treatment compositions are not particularly limited, and compositions for keratin fibers commonly used in the cosmetic field can be employed.
  • the treatment composition can be a hair care composition.
  • the treatment composition may or may not include at least one silicone and/or at least one polyol.
  • the treatment composition which can be included in the treatment composition is the same as the (a) silicone explained above, and the same explanations can be applied.
  • the treatment composition comprises at least one amino-modified silicone.
  • the polyol which can be included in the treatment composition is the same as the polyol explained above, and the same explanations can be applied.
  • the amount of the silicone(s) in the treatment composition may be from 1% to 30% by weight, preferably from 3% to 20% by weight, relative to the total weight of the treatment composition.
  • the treatment composition comprises at least one polyol selected from diols such as ethylene glycol, propylene glycol, and caprylyl glycol and other polyols such as glycerol.
  • diols such as ethylene glycol, propylene glycol, and caprylyl glycol
  • other polyols such as glycerol.
  • the amount of the polyol(s) in the treatment composition may be from 0.1% to 20% by weight, preferably from 1% to 10% by weight, relative to the total weight of the treatment composition.
  • the treatment composition may comprise water. In this embodiment, the treatment composition is not anhydrous.
  • the amount of water in the treatment composition may be from 40% to 95% by weight, preferably from 50% to 95% by weight, and more preferably from 60% to 90% by weight relative to the total weight of the composition.
  • the present invention also relates to a kit for reshaping, preferably straightening keratin fibers such as hair, comprising the combination of the composition A and the composition B of the present invention.
  • the present invention also relates to a kit for reshaping, preferably straightening keratin fibers such as hair, comprising: a composition A comprising:
  • composition B comprising:
  • composition A and the composition B can be provided separately, for example, in different containers.
  • the kit according to the present invention may further comprise at least one heater, such as an iron or a curler, 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.
  • at least one heater such as an iron or a curler, 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.
  • 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 230°C.
  • 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 be a heating iron or a curler as explained in the section titled [Process] above. Also, the details of the composition used in the kit according to the present invention are explained in the section titled [Process] above.
  • the present invention may relate to a use of the combination of the composition A and the composition B of the present invention, for reshaping, preferably straightening keratin fibers such as hair.
  • the present invention also relates to a use of a combination of a composition A and the composition B, for reshaping, preferably straightening keratin fibers such as hair, wherein the composition A comprises:
  • composition B comprises:
  • the present invention relates to a use of the composition A as a pre-treatment agent or a post-treatment agent for reshaping, preferably straightening keratin fibers with the composition B, wherein: the composition A comprises:
  • composition B comprises:
  • the use of the present invention can be performed with heating the keratin fiber, preferably hair.
  • the heating can be provided after the compositions A and B are applied onto the keratin fiber.
  • 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 5O°C and less than 250°C, preferably more than 1OO°C and less than 240°C, and more preferably more than 150°C and less than 230°C.
  • Compositions A and A’ and Composition B were prepared by mixing the ingredients shown in Tables 1 and 2. The numerical values for the amounts of the ingredients are all based on “% by weight” as raw materials.
  • composition A was applied in an amount of 0.2 g onto the wet hair swatch as a pretreatment (Step (i)).
  • the composition B was applied in an amount of 0.6 g onto the hair swatch (Step (ii)).
  • the hair swatch was left for 10 minutes at room temperature (25°C).
  • the hair swatch was then rinsed off thoroughly with tap water, followed by blow-drying with a hair dryer until the hair swatch was dried.
  • 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 (Step (iii)).
  • the hair swatch which was the same as that used in Example 1, was shampooed with 0.5 g of a plain shampoo according to Example 1.
  • the formulation of the plain shampoo was the same as used in Example 1.
  • no treatments was applied on the hair swatch according to Comparative Example 1. Thus, none of steps (i) to (iii) were conducted in this process.
  • a sample according to Comparative Example 2 was prepared by shampooed with 0.5 g of a plain shampoo according to example 1 , then the hair swatch was blow dried with a hair dryer until the hair swatch was dried. Then, the hair swatch was subjected to straightening without any treatments with the hair straightening iron. The straightening process was the same as that of Example 1. Thus, only step (iii) was conducted in this process.
  • step (i) was not conducted in this process.
  • Example 4 A sample according to Comparative Example 4 was prepared in the same manner as Example 1 , Composition A’ was used instead of Composition A in the pre-treatment step. Thus, step (i) of the present invention using the (a) silicone(s) and the (b) plant oils(s) was not conducted in this process.
  • Example 2 A sample according to Example 2 was prepared in the same manner as Example 1 , a hair swatch of Chinese curled hair (type III) was used instead of the hair swatch of Brazilian curled hair (type IV).
  • Example 2 was repeated, but after Composition B was rinsed off with tap water, 0.25 g of a hair care composition Y was applied onto the hair swatch. The hair swatch was left for 5 minutes at room temperature (25 °C), followed by rinsing off thoroughly with tap water.
  • Example 1 a hair care composition Z was applied onto the hair swatch. Then the hair swatch was blow-dried and was subjected to straightening in the same manner as Example 1.
  • Example 3 included additional step (iv).
  • the formulations of the hair care compositions Y and Z are shown in Tables 4 and 5 below, respectively.
  • the numerical values for the amounts of the ingredients are all based on “% by weight” as raw materials.
  • Example 2 was repeated, but Composition A’ was used instead of Composition A in the pretreatment step.
  • step (i) of the present invention using the (a) silicone(s) and the (b) plant oils(s) was not conducted in this process.
  • Example 3 was repeated, but Composition A’ was used instead of Composition A in the pretreatment step.
  • step (i) of the present invention using the (a) silicone(s) and the (b) plant oils(s) was not conducted in this process.
  • composition B was applied in an amount of 0.6 g onto the wet hair swatch as a pretreatment (Step (ii)).
  • the hair swatch was left for 10 minutes at room temperature (25 °C), followed by rinsing off thoroughly with tap water.
  • composition A was applied in an amount of 0.2 g onto the hair swatch (Step (i)) as a post treatment.
  • the hair swatch was then rinsed off thoroughly with tap water again, followed by blow-drying with a hair dryer until the hair swatch was dried.
  • 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 (Step (iii)).
  • Example 4 was repeated, but after Composition A was then rinsed off with tap water, 0.25 g of a hair care composition Y was applied onto the hair swatch. The hair swatch was left for 10 minutes at room temperature (25°C), followed by rinsing off thoroughly with tap water, Then, 0.003 g of a hair care composition Z was applied onto the hair swatch. The hair swatch was left for 10 minutes at room temperature (25°C). Then the hair swatch was blow- dried and was subjected to straightening in the same manner as Example 1.
  • the formulations of the hair care compositions Y and Z were the same as those used in Example 3, shown in Tables 4 and 5 above, respectively.
  • Example 4 was repeated, but Composition A’ was used instead of Composition A in the posttreatment step.
  • step (i) of the present invention using the (a) silicone(s) and the (b) plant oils(s) was not conducted in this process.
  • Example 5 was repeated, but Composition A’ was used instead of Composition A in the posttreatment step.
  • step (i) of the present invention using the (a) silicone(s) and the (b) plant oils(s) was not conducted in this process.
  • the treated hair swatches were evaluated with respect to "ease of combing” and "ease of application of hair iron” in accordance with the following criteria.
  • the hair swatch treated in each of the processes was combed by a trained person and the combing resistance was evaluated under the following criteria.
  • the iron sliding resistance in the application of the hair iron was evaluated by a trained person under the following criteria.
  • the processes according to the examples could provide keratin fibers with good sensory effects, such as “ease of combing” and “ease of application of hair iron”.

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Abstract

La présente invention concerne principalement un procédé de remodelage, de préférence de défrisage de fibres kératiniques telles que les cheveux, comprenant les étapes consistant à : (i) appliquer une composition A sur les fibres kératiniques, la composition A comprenant : (a) au moins une silicone ; et (b) au moins une huile végétale, (ii) appliquer une composition B sur les fibres kératiniques, la composition B comprenant : (c) 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 ; et (d) au moins un composé, différent du composé (c), choisi dans le groupe constitué par les céto-acides, les sels de ceux-ci, et des mélanges de ceux-ci, et (iii) éventuellement chauffer les fibres kératiniques à une température supérieure à 50 °C, de préférence supérieure à 100 °C, et de préférence encore supérieure à 150 °C, le procédé comprenant l'étape (i) puis l'étape (ii) ou l'étape (ii) puis l'étape (i).
PCT/JP2024/080116 2023-07-20 2024-07-12 Procédé de traitement de fibres kératiniques WO2025018433A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2023118442A JP2025015194A (ja) 2023-07-20 2023-07-20 ケラチン繊維を処置するための方法
JP2023-118442 2023-07-20
FR2309005 2023-08-28
FR2309005A FR3152401A3 (fr) 2023-08-28 2023-08-28 Procédé de traitement de fibres kératineuses

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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
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JP2020066575A (ja) 2018-10-22 2020-04-30 株式会社ミルボン 毛髪処理方法、毛髪用第１組成物及び毛髪用第２組成物
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