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WO2025000422A1 - Composition sans silicone pour le conditionnement des cheveux - Google Patents

Composition sans silicone pour le conditionnement des cheveux Download PDF

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Publication number
WO2025000422A1
WO2025000422A1 PCT/CN2023/104402 CN2023104402W WO2025000422A1 WO 2025000422 A1 WO2025000422 A1 WO 2025000422A1 CN 2023104402 W CN2023104402 W CN 2023104402W WO 2025000422 A1 WO2025000422 A1 WO 2025000422A1
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WO
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Prior art keywords
styrene
hydrogenated
composition
mixtures
ethylene
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/CN2023/104402
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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
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Filing date
Publication date
Application filed by LOreal SA filed Critical LOreal SA
Priority to PCT/CN2023/104402 priority Critical patent/WO2025000422A1/fr
Priority to FR2308654A priority patent/FR3150437B3/fr
Publication of WO2025000422A1 publication Critical patent/WO2025000422A1/fr
Anticipated expiration legal-status Critical
Pending legal-status Critical Current

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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
    • A61K8/31—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
    • A61K8/37—Esters of carboxylic 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
    • 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
    • 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
    • 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.
  • Si-free oil product for conditioning the hair which can provide similar conditioning effect with silicone-based oil products and do not deliver greasy sensory.
  • Si-free oil product is stable so that the consumers can apply it conveniently.
  • An object of the present invention is thus to develop Si-free oil products for conditioning the hair, which is stable, can provide similar conditioning effect 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 for conditioning the hair comprising:
  • At least one fatty substance selected from unsaturated fatty compounds comprising a C12-C20 carbon chain, fatty acid ester oils, and mixtures thereof;
  • At least one thickener selected from ester-terminated poly (ester-amide) polymers, optionally hydrogenated block, especially diblock or triblock, copolymers of styrene and olefin, preferably containing one or two ethylenic unsaturations, and/or preferably containing from 2 to 5 carbon atoms, 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 can provide similar conditioning effects as silicone based oil composition, for example a light and silky feeling.
  • silicone free composition means that silicone is not added intentionally in the composition, in particular, the composition comprises no more than 2 wt. %of silicone, relative to the total weight of the composition, more particularly, the composition does not comprise silicone.
  • composition of the present invention comprises:
  • At least one fatty substance selected from unsaturated fatty compounds comprising a C12-C20 carbon chain, fatty acid ester oils and mixtures thereof;
  • At least one thickener selected from ester-terminated poly (ester-amide) polymers, optionally hydrogenated block, especially diblock or triblock, copolymers of styrene and olefin, preferably containing one or two ethylenic unsaturations, and/or preferably containing from 2 to 5 carbon atoms, 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. 101325 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 selected 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
  • Sasol n-dodecane sold by Sasol under the respective references Parafol 12 97 and Parafol 14 97, and also mixtures thereof.
  • branched volatile alkanes for instance 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 will preferably be used.
  • the composition of the present invention comprises at least one volatile alkane selected 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 selected 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.
  • Unsaturated fatty compounds comprising a C12-C20 carbon chain and fatty acid ester oils
  • the composition of the present invention comprises at least one fatty substance selected from unsaturated fatty compounds comprising a C12-C20 carbon chain, fatty acid ester oils, and mixtures thereof.
  • the unsaturated fatty compound is selected from unsaturated fatty alcohol comprising a C12-C20 carbon chain.
  • the unsaturated fatty compound is selected from unsaturated fatty monoalcohol comprising a C12-C20 carbon chain.
  • the unsaturated fatty compound is selected from linear unsaturated fatty monoalcohol comprising a C14-C20 carbon chain.
  • the unsaturated fatty compound is of structure R-OH, wherein R represents a linear alkenyl group comprising from 12 to 20 carbon atoms, preferably from 14 to 20 carbon atoms.
  • the unsaturated fatty compound is oleyl alcohol.
  • the presence of the unsaturated fatty compound can provide conditioning effect without greasiness touch feeling.
  • the unsaturated fatty compound has high affinity to damaged hair fiber especially in wet stage, furthermore the long chain can provide nourish and soft feeling.
  • the fatty acid ester oil is selected 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 room temperature and atmospheric pressure.
  • 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 2 -C 6 aliphatic monoalcohols.
  • 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 provide conditioning effect without greasiness touch feeling.
  • the fatty substance selected from unsaturated fatty compounds comprising a C12-C20 carbon chain, fatty acid ester oils, and mixtures thereof 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 comprises both an unsaturated fatty compound comprising a C12-C20 carbon chain and a fatty acid ester oil.
  • the composition comprises an unsaturated fatty compound comprising a C12-C20 carbon chain in an amount ranging from 0.1 wt. %to 20 wt. %, preferably from 1 wt. %to 15 wt. %, more preferably from 2 wt. %to 10 wt. %and a fatty acid ester oil in an amount ranging from 1 wt. %to 20 wt. %, preferably from 2 wt. %to 15 wt. %, more preferably from 2 wt. %to 10 wt. %, relative to the total weight of the composition.
  • the composition of the present invention comprises at least one thickener selected from ester-terminated poly (ester-amide) polymers, optionally hydrogenated block, especially diblock or triblock, copolymers of styrene and olefin, preferably containing one or two ethylenic unsaturations, and/or preferably containing from 2 to 5 carbon atoms, and mixtures thereof.
  • ester-terminated poly (ester-amide) polymers optionally hydrogenated block, especially diblock or triblock, copolymers of styrene and olefin, preferably containing one or two ethylenic unsaturations, and/or preferably containing from 2 to 5 carbon atoms, 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 cP (centipoises) .
  • 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 2 a 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. 45 Hexadecyloctadecanol-2 having 24 carbon atoms will more particularly 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 approximately 200 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 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 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 must preferably be less than 25, more preferentially less than 15 and more particularly less than 10, more particularly less than 5.
  • the co-diacid When a co-diacid is used to prepare the ETPEA resin, the co-diacid must not represent more than 50%of the carboxylic acid equivalents in the reaction mixture. In other words, 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-diacid When a co-diamine is used to prepare the ETPEA resin, the co-diacid must not represent more than 50%of the carboxylic acid equivalents in the reaction mixture. In other words, 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 acid equivalents 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 particular 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 selected 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 preferably hydrogenated to reduce the residual ethylenic unsaturations after polymerization of the monomers.
  • said thickener is an optionally hydrogenated copolymer, bearing styrene blocks and ethylene and/or C2-C5 and especially C2-C4 alkylene blocks, and especially butylene or propylene.
  • the thickener is a diblock copolymer, which is preferably hydrogenated, bearing styrene blocks and ethylene/C2-C4 alkylene blocks, more particularly a diblock copolymer, which is preferably hydrogenated, bearing styrene blocks and ethylene/propylene (INCI: stryrene/isoprene copolymer) or ethylene/butylene blocks. Mention may also be made of diblock copolymers, which are preferably hydrogenated, 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 triblock copolymer, which is preferably hydrogenated, selected from styrene-ethylene/propylene-styrene copolymers, styrene-ethylene/butadiene-styrene copolymers, styrene-isoprene-styrene copolymers and styrene-butadiene-styrene copolymers.
  • 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 selected from copolymers of hydrogenated dilinoleic acid, of ethylenediamine, of C2-C6 glycol and of C10-C22 monoalcohol, diblock copolymers, which are preferably hydrogenated, bearing styrene blocks and ethylene/C2-C4 alkylene blocks, more particularly copolymers, which are preferably hydrogenated, bearing styrene blocks and ethylene/ethylene or ethylene/propylene or ethylene/butylene blocks, and mixtures thereof.
  • the thickener is selected from hydrogenated styrene/isoprene copolymer, hydrogenated styrene/butadiene copolymer, styrene/isoprene 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 proper 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.
  • 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 30 wt. %, preferably from 5 wt. %to 25 wt. %, more preferably from 10 wt. %to 20 wt. %, relative to the total weight of the composition.
  • composition of the present invention may comprise other cosmetic active ingredient for conditioning the hair, for example oil soluble plant extracts.
  • the cosmetic active ingredient is present in amount ranging from 0.001 wt. %to 5 wt. %, preferably from 0.01 wt. %to 2 wt. %, and more preferably from 0.1 wt. %to 1 wt. %, relative to the total weight of the composition.
  • composition according to the present invention may also comprise an effective amount of other ingredients, such as fragrances, and so on.
  • the present invention provides a silicone free composition for conditioning the hair comprising, relative to the total weight of the composition:
  • at least one thickener selected from hydrogenated styrene/isoprene copolymer, hydrogenated styrene/butadiene copolymer, styrene/isoprene copolymer, Bis-stearyl ethylenediamine/neopentyl glycol/stearyl hydrogenated dimer dilinoleate copolymer and mixtures thereof.
  • 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 cosmeticity/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.
  • Leave-on oils according to invention examples (IE. ) 1-5 and comparative examples (CE. ) 1-3 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 leave-on oil, 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 a silicone oil.
  • Each leave-on oil was prepared as follows, taking that of invention example 1 as an example:
  • the leave-on oils prepared above were evaluated in terms of stability, conditioning effect, and lightness sensory as follows.
  • each composition prepared above was checked after storage at 10°C for 24 hours, 4°C for 1 or 2 months, 45°C for 1 or 2 months, and 50°C for 1 or 2 weeks.
  • composition tested was considered being stable, otherwise, the composition tested was considered being unstable.
  • 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.
  • each leave-on oil 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

Une composition exempte de silicone pour le conditionnement des cheveux comprend : a) au moins un alcane volatil ; b) au moins une substance grasse choisie parmi des composés gras insaturés comprenant une chaîne de carbone en C12-C20, des huiles d'ester d'acide gras, 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 de styrène et d'oléfine, et des mélanges de ceux-ci. Un procédé de conditionnement des cheveux comprend l'application de la composition sur les cheveux.
PCT/CN2023/104402 2023-06-30 2023-06-30 Composition sans silicone pour le conditionnement des cheveux Pending WO2025000422A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/CN2023/104402 WO2025000422A1 (fr) 2023-06-30 2023-06-30 Composition sans silicone pour le conditionnement des cheveux
FR2308654A FR3150437B3 (fr) 2023-06-30 2023-08-11 Composition de revitalisation des cheveux sans silicone

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2023/104402 WO2025000422A1 (fr) 2023-06-30 2023-06-30 Composition sans silicone pour le conditionnement des cheveux

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102666645A (zh) * 2009-12-23 2012-09-12 雅芳产品公司 嵌段共聚物和酯封端聚酯酰胺组合物及其用途
US20160151272A1 (en) * 2013-07-04 2016-06-02 L'oreal Cosmetic composition comprising liquid fatty esters, volatile oils and thickeners, and cosmetic treatment processes
US20200188284A1 (en) * 2018-12-17 2020-06-18 Henkel Ag & Co. Kgaa Hair oils for conditioning keratin fibres
US20200188287A1 (en) * 2018-12-17 2020-06-18 Henkel Ag & Co. Kgaa Cosmetic agents for conditioning keratin fibres
CN112384285A (zh) * 2018-07-02 2021-02-19 莱雅公司 包含酯-封端的聚(酯-酰胺)聚合物、挥发性烷烃、增粘树脂和至少一种颜料的组合物

Family Cites Families (3)

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Publication number Priority date Publication date Assignee Title
US3157681A (en) 1962-06-28 1964-11-17 Gen Mills Inc Polymeric fat acids
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 (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102666645A (zh) * 2009-12-23 2012-09-12 雅芳产品公司 嵌段共聚物和酯封端聚酯酰胺组合物及其用途
US20160151272A1 (en) * 2013-07-04 2016-06-02 L'oreal Cosmetic composition comprising liquid fatty esters, volatile oils and thickeners, and cosmetic treatment processes
CN112384285A (zh) * 2018-07-02 2021-02-19 莱雅公司 包含酯-封端的聚(酯-酰胺)聚合物、挥发性烷烃、增粘树脂和至少一种颜料的组合物
US20200188284A1 (en) * 2018-12-17 2020-06-18 Henkel Ag & Co. Kgaa Hair oils for conditioning keratin fibres
US20200188287A1 (en) * 2018-12-17 2020-06-18 Henkel Ag & Co. Kgaa Cosmetic agents for conditioning keratin fibres

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FR3150437B3 (fr) 2025-08-15

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