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WO2025231576A1 - Composition sans silicone pour le conditionnement des cheveux - Google Patents

Composition sans silicone pour le conditionnement des cheveux

Info

Publication number
WO2025231576A1
WO2025231576A1 PCT/CN2024/091132 CN2024091132W WO2025231576A1 WO 2025231576 A1 WO2025231576 A1 WO 2025231576A1 CN 2024091132 W CN2024091132 W CN 2024091132W WO 2025231576 A1 WO2025231576 A1 WO 2025231576A1
Authority
WO
WIPO (PCT)
Prior art keywords
styrene
composition
chosen
hydrogenated
mixtures
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
PCT/CN2024/091132
Other languages
English (en)
Inventor
Lili Yang
Jingting TANG
Lingchao KONG
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
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
Application filed by LOreal SA filed Critical LOreal SA
Priority to PCT/CN2024/091132 priority Critical patent/WO2025231576A1/fr
Priority to FR2406552A priority patent/FR3161851A3/fr
Publication of WO2025231576A1 publication Critical patent/WO2025231576A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • 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
    • A61K8/31—Hydrocarbons
    • 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
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—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
    • A61K8/88—Polyamides
    • 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
    • A61K8/90—Block copolymers
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A61K2800/34—Free of silicones

Definitions

  • the present invention relates to a composition for conditioning the hair.
  • the present invention relates to a silicone free composition for conditioning the hair.
  • the present invention also relates to a process for conditioning the hair.
  • the hair is generally damaged and weakened by the action of external atmospheric agents such as light, weather, and/or the action of mechanical or chemical treatments such as brushing, combing, dyeing, bleaching, permanent and/or straightening.
  • silicone free oil product for conditioning the hair which can provide similar conditioning effect with silicone-based oil products and do not deliver greasy sensory.
  • silicone free oil product is stable so that the consumers can apply it conveniently.
  • An object of the present invention is thus to develop silicone free oil products for conditioning the hair, which is stable, can provide similar or better conditioning effect as compared with silicone-based oil products and do not deliver greasy sensory.
  • Another object of the present invention is to provide a process for conditioning the hair.
  • the present invention provides a silicone free composition, preferably for conditioning the hair comprising:
  • At least one fatty compound chosen from saturated fatty alcohols, saturated fatty acids, and mixtures thereof;
  • At least one thickener chosen from ester-terminated poly (ester-amide) polymers, hydrogenated block copolymers of styrene and olefin, and mixtures thereof.
  • the present invention provides a process for conditioning the hair comprising applying the composition as described above onto the hair.
  • the composition of the present invention is stable, can provide similar or better conditioning effects, for example a silky feeling, as compared with silicone-based oil composition, and can provide a light sensory.
  • silicone free composition means that the composition contains less than 2 wt. %and preferably less than 1 wt. %of silicone, relative to the total weight of the composition, more preferably contains no silicone. Where appropriate, the small amounts of silicone may be provided by ingredients of the composition that contain it in residual amount but are not deliberately provided.
  • composition of the present invention comprises:
  • At least one thickener chosen from ester-terminated poly (ester-amide) polymers, hydrogenated block copolymers of styrene and olefin, and mixtures thereof.
  • composition of the present invention comprises at least one volatile alkane.
  • alkane is intended to mean any compound comprising a linear or branched, saturated, hydrocarbon-based chain constituted exclusively of carbon atoms and hydrogen atoms.
  • volatile alkane that is suitable for use in the present invention is intended to mean an alkane which is capable of evaporating on contact with the skin in less than one hour, at ambient temperature (25°C) and atmospheric pressure (760 mmHg, i.e., 101 325 Pa) , which is liquid at ambient temperature, especially having an evaporation rate ranging from 0.01 to 15 mg/cm 2 /minute, at ambient temperature (25°C) and atmospheric pressure (760 mmHg) .
  • volatile linear alkanes that are suitable for use in the present invention are preferably chosen from volatile linear alkanes comprising from 7 to 14 carbon atoms.
  • alkanes that are suitable for the present invention, mention may be made of the alkanes described in patent applications WO 2007/068371 and WO 2008/155059 from the company Cognis (mixtures of distinct alkanes differing by at least one carbon) . These alkanes are obtained from fatty alcohols, which are themselves obtained from copra oil or palm oil.
  • linear alkanes that are suitable for use in the present invention, mention may be made of n-heptane (C 7 ) , n-octane (C 8 ) , n-nonane (C 9 ) , n-decane (C 10 ) , n-undecane (C 11 ) , n-dodecane (C 12 ) , n-tridecane (C 13 ) and n-tetradecane (C 14 ) , and mixtures thereof.
  • n-dodecane C 12
  • n-tetradecane C 14
  • the branched linear alkanes that are suitable for use in the present invention are preferably chosen from branched C 8 -C 16 alkanes, for instance C 8 -C 16 isoalkanes of petroleum origin (also known as isoparaffins) , for instance isododecane (also known as 2, 2, 4, 4, 6-pentamethylheptane) , isodecane and isohexadecane, and mixtures thereof. Isododecane and isohexadecane are more preferably be used.
  • the composition of the present invention comprises at least one volatile alkane chosen from linear C 7 -C 14 alkanes, branched C 8 -C 16 alkanes and mixtures thereof.
  • the composition of the present invention comprises at least one volatile alkane chosen from n-undecane (C11) , n-tridecane (C13) , isododecane, isohexadecane, and mixtures thereof.
  • the composition of the present invention comprises a combination of n-undecane (C11) , n-tridecane (C13) , isododecane and isohexadecane.
  • the volatile alkane can deliver excellent spread ability on hair with no greasiness.
  • the volatile alkane is present in the composition of the present invention in an amount ranging from 1 wt. %to 90 wt. %, preferably from 10 wt. %to 80 wt. %, more preferably from 20 wt. %to 80 wt. %, relative to the total weight of the composition.
  • the composition of the present invention comprises at least one fatty compound chosen from saturated fatty alcohols, saturated fatty acids, and mixtures thereof.
  • fatty compound is intended to mean an organic compound that is insoluble in water at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg or 1.013 ⁇ 10 5 Pa) (solubility of less than 5%and preferably of less than 1%, more preferably still of less than 0.1%) .
  • the fatty compound is generally soluble in organic solvents under the same temperature and pressure conditions, for instance chloroform, dichloromethane, carbon tetrachloride, ethanol, benzene, toluene, tetrahydrofuran (THF) , liquid petroleum jelly or decamethylcyclopentasiloxane.
  • saturated fatty alcohol here means an alcohol having a long aliphatic saturated carbon chain. It is preferable that the saturated fatty alcohol be chosen from any linear or branched, saturated C6-C30 fatty alcohols. Among the linear or branched, saturated C6-C30 fatty alcohols, linear or branched, saturated C8-C20 fatty alcohols are preferably used. Any linear or branched, saturated C10-C20 fatty alcohols are even more preferably used. Linear C12-C20 fatty alcohols are even more preferably used, linear C12-C16 fatty alcohol are most preferably used.
  • saturated fatty alcohols mention may be made of lauryl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, behenyl alcohol, undecylenyl alcohol, myristyl alcohol, octyldodecanol, hexyldecanol, and mixtures thereof.
  • the fatty alcohol used in the composition according to the present invention is chosen from lauryl alcohol, cetyl alcohol, octyldodecanol, hexyldecanol, and mixtures thereof.
  • the saturated fatty alcohol used in the composition according to the present invention is lauryl alcohol.
  • the composition of the present invention comprises at least one fatty compound chosen from saturated fatty acids.
  • saturated fatty acid here means an acid having a long aliphatic saturated carbon chain. It is preferable that the saturated fatty acid be chosen from any linear or branched, saturated C6-C30 fatty acids. Among the linear or branched, saturated C6-C30 fatty acids, linear or branched, saturated C8-C20 fatty acids are preferably used. Any linear or branched, saturated C10-C20 fatty acids are more preferably used.
  • saturated fatty acids mention can be made of, for example, lauric acid, palmitic acid, heptadecanoic acid, stearic acid, nonadecanoic acid, arachidic acid, behenic acid, tetradocosanoic acid, hexadocosanoic acid, and octadocosanoic acid.
  • the fatty compound chosen from saturated fatty alcohols, saturated fatty acids, and mixtures thereof is present in the composition according to the present invention in an amount ranging from 0.1 wt. %to 20 wt. %, preferably from 0.5 wt. %to 15 wt. %, more preferably from 1 wt. %to 10 wt. %, relative to the total weight of the composition.
  • the presence of the saturated fatty compound as defined above can provide conditioning effect without greasiness touch feeling.
  • the saturated fatty compound has high affinity to damaged hair fiber especially in wet stage, furthermore the long chain can provide nourish and soft feeling.
  • the composition of the present invention comprises at least one thickener chosen from ester-terminated poly (ester-amide) polymers, hydrogenated block copolymers of styrene and olefin, and mixtures thereof.
  • thickener means a compound that is capable, by virtue of its presence, at 25°C, of increasing the viscosity of the composition in which it is present, preferably by at least 50 mPa ⁇ s.
  • ester-terminated poly (ester-amide) (ETPEA) polymer is preferably in the form of a resin prepared by reacting a diacid, a diamine, a polyol and a monoalcohol in which:
  • At least 50 equivalent%of said diacid comprises a polymerized fatty acid
  • the resin composition is such that
  • ester-terminated poly (ester-amide) (ETPEA) polymers can be prepared according to the process described in patent US 6 552 160.
  • the diacid is in general an organic molecule containing two carboxylic acid groups or equivalent reactive groups.
  • the diacid is a polymerized fatty acid.
  • the polymerized fatty acid is typically a mixture comprising an acid dimer and an acid trimer where each dimer may be saturated, unsaturated, cyclic or acyclic, etc.
  • the polymerized fatty acid used for the synthesis of the ester-terminated poly (ester-amide) (ETPEA) polymer is preferably an acid dimer.
  • the polymerized fatty acid is in general formed by heating long-chain unsaturated fatty acids, for example C 18 monocarboxylic acids, at temperatures of about 200-250°C in the presence of a catalyst clay in order to polymerize the fatty acids.
  • the product obtained comprises in general an acid dimer, in particular a C 36 dicarboxylic acid formed by dimerization of the fatty acid and an acid trimer, in particular a C 54 tricarboxylic acid obtained by trimerization of the carboxylic acid.
  • Greater details regarding the polymerization of fatty acids are indicated in particular in patent US 3 157 681 and the book “Naval Stores--Production, Chemistry and Utilization, D.F. Zinkel and J. Russell (eds. ) , Pulp. Chem. Assoc. Inc., 1989, Chapter 23” .
  • the polymerized fatty acid contains less than 20%by weight of acid trimer and at least 80%by weight of acid dimer relative to the total weight of the polymerized fatty acid. More particularly, the acid dimer constitutes essentially all of the polymerized fatty acid.
  • the unsaturated fatty acids used to form the polymerized fatty acid mention may be made of oleic acid, linoleic acid and linolenic acid.
  • Use is preferably made of long-chain fatty acid oils which are mixtures of long-chain unsaturated acids obtained by means of a wood-pulp reduction process.
  • Use may also be made of other sources, such as soybeans or canola seeds.
  • the polymerized fatty acid that can be used according to the invention has an acid number of about 180 to 200.
  • the polymerized fatty acid may be hydrogenated before being used in the resin formation reaction. Hydrogenation makes it possible to obtain a slightly higher melting point of the resin and also a greater stability with respect to oxidation and of the colour in the case of a slightly coloured resin.
  • polymerized fatty acids and in particular the hydrogenated forms that are commercially available, mention may be made of the product sold under the brand Unidyme by the company Arizona Chemical, the product sold under the brand Pripol 1015 by the company Uniqema, or the product sold under the brand Empol 1008 by the company Cognis.
  • the diacid may comprise a co-diacid of formula: HOOC-R 1 -COOH where R 1 is a C 4 -C 19 , preferably C 4 -C 12 and more preferentially C 4 -C 8 hydrocarbon-based compound.
  • the carbon atoms may be arranged in linear, branched or cyclic form and an unsaturation may be present between two adjacent atoms.
  • R 1 may be aliphatic or aromatic.
  • the diamine reagent possesses two amine groups which are preferably primary amines and represented by the formula: HN (R 2a ) -R 2 -N (R 2a ) H in which R 2a denotes hydrogen or an alkyl group or else forms, with R 2 or another radical R 2a , a heterocycle.
  • R 2a is hydrogen and R 2 is-CH 2 -CH 2 -.
  • the diamines other than ethylenediamine will be denoted in the text as co-diamines. When they are present, the co-diamines are used in low amounts relative to the ethylenediamine.
  • the monoalcohol may be represented by the formula R 3 -OH where R 3 is preferably a hydrocarbon-based group having at least 10 carbon atoms.
  • R 3 is preferably a hydrocarbon-based group having at least 10 carbon atoms.
  • the monoalcohol may be described as a monohydric alcohol.
  • R 3 is a C 10 -C 30 hydrocarbon-based group, preferentially a C 12 -C 24 hydrocarbon-based group and even more particularly a C 18 hydrocarbon-based radical.
  • C 10 -C 30 hydrocarbon-based group is intended to mean any group having at least 10 carbon atoms but at most 30 carbon atoms.
  • the carbon atoms may be arranged in a linear, branched, or cyclic manner and the hydrocarbon-based radical may be saturated or unsaturated.
  • R 3 is linear, and the hydroxyl group is located on an end carbon: i.e., the monoalcohol is primary.
  • the monoalcohols that can be used to prepare the ETPEA resin, mention may be made of 1-dodecanol, 1-tetradecanol, 1-hexadecanol (cetyl alcohol) , 1-octadecanol (stearyl alcohol) , 1-eicosanol (arachidyl alcohol) and 1-docosanol (behenyl alcohol) .
  • the reactive monoalcohol may contain an alkylene group, i.e., an alkyl group with an unsaturation between two adjacent carbon atoms.
  • Another reactive monoalcohol that can be used according to the invention may be a Guerbet alcohol of formula: H-C (R a ) (R b ) -CH 2 -OH where R a and R b , which may be identical or different, preferably denote a C 6 -C 12 hydrocarbon-based group.
  • Guerbet alcohols are in particular described in the book "Dictionary For Auxiliaries For Pharmacy, Cosmetics And Related Fields, " H.P. Fiedler, 3rd Ed., 1989, Cantor Aulendorf. Hexadecyloctadecanol-2 having 24 carbon atoms will more particularly preferred be used.
  • linear alcoholic wax Another type of reactive monoalcohol that can be used according to the invention is a linear alcoholic wax.
  • linear alcoholic waxes available on the market, mention may be made of the products sold under the brand Unilin by the company Petrolite Corporation (Tulsa, Okla. ) .
  • These linear alcoholic waxes are in general a mixture of linear alcohols having at least 20 carbon atoms and more particularly at least 24 carbon atoms.
  • VPO Vapour-Pressure Osmometry
  • the mixture of linear monoalcoholic waxes has a number-average molecular weight measured by VPO of approximately200 to approximately 800, preferably of approximately 300 to approximately 600.
  • a pure C22 monohydric linear alcohol has a molecular weight measured by VPO of 326.
  • a pure monoalcohol or a mixture of linear monoalcohols such as, for example: 1-eicosanol (C 20 ) , 1-docosanol (C 22 , behenyl alcohol) , dotriacontanol (C 32 ) , tetratriacontanol (C 34 ) , pentatriacontanol (C 35 ) , tetracontanol (C 40 ) , tetraacontanol (C 44 ) , dopentaacontanol (C 54 ) , tetrahexaacontanol (C 64 ) , dohexaacontanol (C 72 ) .
  • 1-eicosanol C 20
  • 1-docosanol C 22
  • behenyl alcohol dotriacontanol
  • C 34 tetratriacontanol
  • Use will more particularly preferably be made of 1-octadecanol, more commonly known as stearyl alcohol.
  • a final ingredient required for the preparation of the ETPEA resin is a polyol or polyhydric alcohol.
  • the structure of the polyol is: R 4 (OH) n where R 4 denotes an n-valent organic group.
  • R 4 may be a C 2 -C 20 organic group with no hydroxyl substitution.
  • R 4 may be a hydrocarbon-based group.
  • n is in general equal to 2, 3, 4, 5 or 6.
  • Neopentyl glycol will more particularly preferably be used.
  • Reagents that are equivalents of the diacids and/or reagents that are equivalent to the diamines may also be used to prepare the ETPEA resin.
  • diesters may be used in place of some or all the diacids in the reaction forming the ETPEA resin.
  • the term “diester” is intended to mean any product of esterification of a diacid with molecules comprising a hydroxyl function. Such diesters are preferably obtained from relatively volatile molecules containing hydroxyl functions in order for said molecules to be able to easily be removed from the reaction vessel after the reaction of the monoalcohol and/or of the diamine with the diester.
  • a lower diester in particular a product of esterification or diesterification of a diacid as defined above with a C 1 -C 4 monoalcohol (i.e.: methanol, ethanol, propanol and butanol) , may be used in place of some or all the diacids in the reaction forming the ETPEA resin.
  • Acid halides may also be used in place of some or all the diacids in the reaction forming the ETPEA resin.
  • the monoalcohol can be esterified with a volatile diacid, for example: acetic acid, before being used in the reaction forming the ETPEA resin.
  • Such equivalent reagents are not however preferential in so far as they introduce reactive groups into the reaction vessel.
  • the carboxylic acid equivalents must be substantially equal to the combined equivalents of hydroxyl introduced by the monoalcohol and the polyol and of amine introduced by the diamine.
  • each of the acid numbers and amine numbers of the resin in accordance with the invention are preferably less than 25, more preferentially less than 15 and more particularly less than 10, more particularly less than 5.
  • the co-diacid does not represent more than 50%of the carboxylic acid equivalents in the reaction mixture.
  • the co-diacid represents from 0 to 50%equivalents, more preferentially from 0 to 25%and even more preferentially from 0 to 10%of the acid equivalents in the reaction mixture.
  • the co-diamine does not represent more than 50%of the diamines equivalents in the reaction mixture.
  • the co-diamine represents from 0 to 50%equivalents, more preferentially from 0 to 25%and even more preferentially from 0 to 10%of the diamines in the reaction mixture.
  • the hydroxyl equivalents originating from the polyol are preferably less than or equal to 50%relative to all the hydroxyl equivalents and amine equivalents introduced by the polyol, monoalcohol and diamine reagents. According to one particularly preferred embodiment of the invention, the hydroxyl equivalents originating from the polyol may be less than or equal to 40%, or less than or equal to 30%or even less than or equal to 20%relative to all the hydroxyl equivalents and amine equivalents introduced by the polyol, monoalcohol and diamine reagents.
  • the amine equivalents preferably range from 0.3 to 0.75 relative to all the hydroxyl equivalents and amine equivalents introduced by the polyol, monoalcohol and diamine reagents.
  • the hydroxyl equivalents originating from the polyol range from 0.05 to 0.45 relative to all the hydroxyl equivalents and amine equivalents introduced by the polyol, monoalcohol and diamine reagents.
  • the hydroxyl equivalents originating from the monoalcohol range from 0.20 to 0.45 relative to all the hydroxyl equivalents and amine equivalents introduced by the polyol, monoalcohol and diamine reagents.
  • ester-terminated poly (ester-amide) polymer chosen from copolymers of hydrogenated dilinoleic acid, of ethylenediamine, of C2-C6 glycol and of C10-C22 monoalcohol.
  • ester-terminated poly (ester-amide) polymer having the INCI name Polyamide-8 which is a copolymer of hydrogenated dilinoleic acid, of ethylenediamine, of neopentyl glycol and of stearyl alcohol.
  • This copolymer is in particular sold under the trade name LP-20-PA sold by the company Croda.
  • olefins examples include ethylenic carbide monomers especially containing one or two ethylenic unsaturations, containing from 2 to 5 carbon atoms, such as ethylene, propylene, butylene, butadiene, and isoprene.
  • the polymeric thickener of block polymer type is hydrogenated to reduce the residual ethylenic unsaturations after polymerization of the monomers.
  • the thickener is a hydrogenated diblock copolymer, bearing styrene blocks and ethylene/C2-C4 alkylene blocks, more particularly a hydrogenated diblock copolymer, bearing styrene blocks and ethylene/propylene (INCI: stryrene/isoprene copolymer) or ethylene/butylene blocks. Mention may also be made of hydrogenated diblock copolymers, bearing styrene and ethylene/butadiene blocks. Such diblock polymers are commercially available under the name Kraton G1701 by the company Kraton Polymers.
  • the thickener may also be a hydrogenated triblock copolymer, of styrene-ethylene/propylene-styrene, styrene-ethylene/butadiene-styrene, styrene-isoprene-styrene or styrene-butadiene-styrene.
  • triblock polymers are especially commercially available under the names G1650, G1652, D1101, D1102 and D1160 by the company Kraton Polymers.
  • a mixture of hydrogenated styrene-butylene/ethylene-styrene triblock copolymer and of ethylene-propylene-styrene hydrogenated star polymer may also be used, such a mixture especially being in isododecane.
  • Such mixtures are sold, for example, by the company Penreco under the trade names M5960 and M5670.
  • the thickeners are chosen from copolymers of hydrogenated dilinoleic acid, of ethylenediamine, of C2-C6 glycol and of C10-C22 monoalcohol, hydrogenated diblock copolymers, bearing styrene blocks and ethylene/C2-C4 alkylene blocks, more particularly hydrogenated copolymers bearing styrene blocks and ethylene/ethylene or ethylene/propylene or ethylene/butylene blocks, and mixtures thereof.
  • the thickener is chosen from hydrogenated styrene/isoprene copolymer, hydrogenated styrene/butadiene copolymer, bis-stearyl ethylenediamine/neopentyl glycol/stearyl hydrogenated dimer dilinoleate copolymer, and mixtures thereof.
  • the thickener suitable for the present invention is highly compatible with the oil used in the composition of the present invention so as to deliver a suitable viscosity.
  • the thickener is present in the composition of the present invention in an amount ranging from 0.1 wt. %to 15 wt. %, preferably from 1 wt. %to 10 wt. %, more preferably from 2 wt. %to 8 wt. %, relative to the total weight of the composition.
  • composition according to the present invention further comprises at least one fatty acid ester oil.
  • the fatty acid ester oil is chosen from liquid monoesters of saturated or unsaturated, branched C 3 -C 26 aliphatic monoacid or polyacids and of saturated or unsaturated, branched C 3 -C 26 aliphatic monoalcohol or polyalcohol.
  • oil means a fatty substance that is in liquid form at ambient temperature (25°C) and atmospheric pressure (760 mmHg) .
  • the fatty acid ester oil of the present invention is liquid monoesters of saturated or unsaturated, branched C 3 -C 26 aliphatic monoacids and of saturated or unsaturated, branched C 3 -C 26 aliphatic monoalcohols, the total number of carbon atoms of the esters being preferably greater than or equal to 10, and preferably less than or equal to 30.
  • the fatty acid ester oil is liquid monoesters of saturated or unsaturated, branched C 3 -C 22 aliphatic monoacids and of saturated or unsaturated, branched C 3 -C 20 aliphatic monoalcohols. More preferably, the fatty acid ester oil is liquid monoesters of saturated, branched C 6 -C 20 aliphatic monoacids and of saturated, branched C 3 -C 6 aliphatic monoalcohols.
  • the preferred esters may have the following formula:
  • R 1 represents a branched, preferably branched alkyl radical of 3 to 22 carbon atoms, preferably of 6 to 20 carbon atoms
  • R 2 represents a branched, preferably branched alkyl radical of 3 to 20 carbon atoms, preferably of 3 to 6 carbon atoms.
  • the total number of carbon atoms of R 1 +R 2 may be 9 or more, preferably 12 or more, more preferably 16 or more, and most preferably 20 or more.
  • the esters may be, for example, hexanoate, nonanoate, isononanoate, caprates, laurates, myristates, palmitates, stearates, isostearates, behenates, and mixtures thereof.
  • ethyl hexyl palmitate isopropyl palmitate, isopropyl isostearate, alkyl myristates such as isopropyl myristate, isocetyl stearate, 2-ethylhexyl isononanoate, and isononyl isononanoate.
  • preferable fatty acid ester oils mention may be made of, for example, isohexyl laurate, isopropyl myristate, isopropyl palmitate, isopropy stearate, isopropyl isostearate, and mixtures thereof.
  • the most preferred fatty acid ester oil is isopropyl isostearate.
  • the presence of the fatty acid ester oil can further improve conditioning effect without greasiness touch feeling.
  • the fatty acid ester oil is present in the composition of the present invention in an amount ranging from 0.1 wt. %to 40 wt. %, preferably from 1 wt. %to 30 wt. %, more preferably from 2 wt. %to 20 wt. %, relative to the total weight of the composition.
  • the composition of the present invention further comprises a linear C15-C19 alkane and/or a branched C17-C19 alkane, in particular, abranched C17-C19 alkane.
  • the linear C15-C19 alkane and/or branched C17-C19 alkane, in particular, branched C17-C19 alkane is present in the composition of the present invention in an amount ranging from 2 wt. %to 50 wt. %, preferably from 5 wt. %to 40 wt. %, more preferably from 10 wt. %to 30 wt. %, relative to the total weight of the composition.
  • composition of the present invention may comprise other cosmetic active ingredients for conditioning the hair.
  • composition according to the present invention may also comprise one or more cosmetic adjuvants.
  • the composition may comprise one or more adjuvants that are well known in the art, such as antioxidants, pH adjusters, and preserving agents.
  • adjuvants that are well known in the art, such as antioxidants, pH adjusters, and preserving agents.
  • the present invention provides a silicone free composition, preferably for conditioning the hair comprising, relative to the total weight of the composition:
  • the composition according to the present invention is anhydrous.
  • anhydrous means that the composition contains less than 2 wt. %and preferably less than 1 wt. %of water, relative to the total weight of the composition, more preferably contains no water.
  • the small amounts of water may be provided by ingredients of the composition that contain it in residual amount but are not deliberately provided.
  • composition according to the present invention can be prepared by mixing ingredients a) to c) , as essential ingredients, as well as additional ingredient (s) , as explained above.
  • the method and means to mix the above essential and optional ingredients are not limited. Any conventional method and means can be used to mix the above essential and optional ingredients to prepare the composition according to the present invention.
  • composition according to the present invention does not comprise silicone, it can deliver similar wet/dry cosmetic/conditioning effect as compared to silicone base oil compositions.
  • composition according to the present invention can be used as a conditioning leave-on or rinse-off product for haircare.
  • the present invention provides a process for conditioning the hair comprising applying the composition as described above onto the hair.
  • compositions of invention examples (IE. ) 1-5 and comparative examples (CE. ) 1-4 were prepared with the ingredients listed in Table 2 (the contents are expressed as weight percentages of ingredients with regard to the total weight of each composition, unless otherwise indicated) .
  • Polyamide-8* is Bis-stearyl ethylenediamine/neopentyl glycol/stearyl hydrogenated dimer dilinoleate copolymer.
  • compositions of invention examples 1-5 represent compositions according to the present invention.
  • compositions of comparative examples 1-2 comprise dextrin palmitate instead of a thickener according to the present invention.
  • Composition of comparative example 3 comprises caprylic/capric triglyceride instead of at least one saturated fatty compound chosen from fatty alcohols, fatty acids, and mixtures thereof.
  • Composition of comparative example 4 comprises a silicone oil instead of at least one saturated fatty compound chosen from fatty alcohols, fatty acids, and mixtures thereof.
  • composition was prepared as follows:
  • Phase B -adding all the ingredients of Phase B into a beaker, heating to 80°C with stirring until a homogenous mixture was obtained;
  • compositions prepared above were evaluated in terms of stability, conditioning effect, and lightness sensory.
  • each composition prepared above was checked after storage at-10°C for 24 hours, 4°C and 45°C for 2 months, and 50°C for 2 weeks.
  • composition tested was considered being stable, otherwise, the composition tested was considered being unstable.
  • Natural hair swatches were washed with a silicone free shampoo (0.4 g/per gram of hair swatch) , and dried with a towel until there is no dripping water.
  • rank 4 a little bit sticky
  • each composition of invention examples 1-5 are stable, and can deliver good conditioning effect and lightness sensory, i.e., does not deliver a greasy sensory.

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Abstract

L'invention concerne une composition sans silicone, de préférence pour le conditionnement des cheveux, comprenant : a) au moins un alcane volatil ; b) au moins un composé gras choisi parmi des alcools gras saturés, des acides gras saturés, et des mélanges de ceux-ci ; et c) au moins un épaississant choisi parmi des polymères de poly(ester-amide) à terminaison ester, des copolymères séquencés hydrogénés de styrène et d'oléfine et des mélanges de ceux-ci. L'invention concerne également un procédé de conditionnement des cheveux comprenant l'application de la composition telle que décrite ci-dessus sur les cheveux.
PCT/CN2024/091132 2024-05-06 2024-05-06 Composition sans silicone pour le conditionnement des cheveux Pending WO2025231576A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/CN2024/091132 WO2025231576A1 (fr) 2024-05-06 2024-05-06 Composition sans silicone pour le conditionnement des cheveux
FR2406552A FR3161851A3 (fr) 2024-05-06 2024-06-19 Composition de revitalisation des cheveux sans silicone

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2024/091132 WO2025231576A1 (fr) 2024-05-06 2024-05-06 Composition sans silicone pour le conditionnement des cheveux

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WO2025231576A1 true WO2025231576A1 (fr) 2025-11-13

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100068163A1 (en) * 2005-07-13 2010-03-18 L'oreal Keratin Fibre Coating Composition Comprising a Liquid Fatty Phase and a Tackifying Resin
WO2016065437A1 (fr) * 2014-10-31 2016-05-06 L'oreal Composition de conditionnement cosmétique comprenant une phase aqueuse cationique
US20160151272A1 (en) * 2013-07-04 2016-06-02 L'oreal Cosmetic composition comprising liquid fatty esters, volatile oils and thickeners, and cosmetic treatment processes
CN110461300A (zh) * 2017-03-20 2019-11-15 总和营销服务 生物来源的胶凝化组合物
WO2020042138A1 (fr) * 2018-08-31 2020-03-05 L'oreal Composition pour le conditionnement de fibres de kératine
CN115867250A (zh) * 2020-07-31 2023-03-28 莱雅公司 皮肤紧致化妆品组合物及使用方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3157681A (en) 1962-06-28 1964-11-17 Gen Mills Inc Polymeric fat acids
US6552160B2 (en) 2001-05-14 2003-04-22 Arizona Chemical Company Ester-terminated poly(ester-amides) useful for formulating transparent gels in low polarity fluids
EP1798213A1 (fr) 2005-12-14 2007-06-20 Cognis IP Management GmbH Procédé pour la production d'hydrocarbures
WO2008155059A2 (fr) 2007-06-19 2008-12-24 Cognis Ip Management Gmbh Mélanges d'hydrocarbures et leur utilisation

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100068163A1 (en) * 2005-07-13 2010-03-18 L'oreal Keratin Fibre Coating Composition Comprising a Liquid Fatty Phase and a Tackifying Resin
US20160151272A1 (en) * 2013-07-04 2016-06-02 L'oreal Cosmetic composition comprising liquid fatty esters, volatile oils and thickeners, and cosmetic treatment processes
WO2016065437A1 (fr) * 2014-10-31 2016-05-06 L'oreal Composition de conditionnement cosmétique comprenant une phase aqueuse cationique
CN110461300A (zh) * 2017-03-20 2019-11-15 总和营销服务 生物来源的胶凝化组合物
WO2020042138A1 (fr) * 2018-08-31 2020-03-05 L'oreal Composition pour le conditionnement de fibres de kératine
CN115867250A (zh) * 2020-07-31 2023-03-28 莱雅公司 皮肤紧致化妆品组合物及使用方法

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