WO2012072765A1 - Cosmetic composition containing a non-amino silicone, a liquid fatty ester and an amino silicone, process and use - Google Patents

Cosmetic composition containing a non-amino silicone, a liquid fatty ester and an amino silicone, process and use Download PDF

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Publication number
WO2012072765A1
WO2012072765A1 PCT/EP2011/071557 EP2011071557W WO2012072765A1 WO 2012072765 A1 WO2012072765 A1 WO 2012072765A1 EP 2011071557 W EP2011071557 W EP 2011071557W WO 2012072765 A1 WO2012072765 A1 WO 2012072765A1
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weight
carbon atoms
chosen
amino
radical
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PCT/EP2011/071557
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French (fr)
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Claire Bourdin
Charles Gringore
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L'oreal
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Priority to BR112013013626-0A priority Critical patent/BR112013013626B1/en
Priority to EP11790971.3A priority patent/EP2645984A1/en
Publication of WO2012072765A1 publication Critical patent/WO2012072765A1/en

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    • 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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/03—Liquid compositions with two or more distinct layers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/046—Aerosols; Foams
    • 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
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • 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
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/892—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a hydroxy group, e.g. dimethiconol
    • 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
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers

Definitions

  • the present invention relates to novel cosmetic compositions comprising one or more non-amino silicones, one or more particular liquid fatty esters and one or more particular amino silicones.
  • conditioners in particular cationic or amphoteric polymers, fatty acid esters or volatile or non-volatile non-amino silicones in compositions for washing or caring for keratin materials such as the hair, in order to facilitate disentangling of the hair and to give it softness and manageability.
  • conditioners in particular cationic or amphoteric polymers, fatty acid esters or volatile or non-volatile non-amino silicones
  • the cosmetic advantages mentioned above are also unfortunately accompanied, on dried hair, by certain cosmetic effects considered to be undesirable, namely lankness of the hairstyle (lack of lightness of the hair) and lack of smoothness (hair not uniform from the root to the end).
  • Amino silicones are generally used in cosmetic compositions as conditioners for improving the softness and the disentangling of the hair.
  • a cosmetic composition in particular a detergent composition, especially a shampoo, which has a satisfactory aesthetic appearance, which is stable and which makes it possible to obtain good cosmetic performance on the keratin materials, namely in particular the hair and the scalp, and more particularly sensitized hair.
  • compositions of the present invention makes it possible to obtain, on keratin materials, in particular the hair, very good cosmetic properties particularly in terms of lightness, disentangling, smooth feel, body and sheen. It has also been noted that the compositions of the invention make it possible to obtain dried hair that looks generally smoother.
  • compositions comprise foaming surfactants, their foaming properties, in particular the initiation of foam, are not degraded.
  • compositions rinse out easily.
  • compositions of the invention applied to the skin in particular in the form of a bubble bath or of a shower gel, give an improvement in the softness of the skin.
  • novel cosmetic compositions comprising:
  • a subject of the invention is also the use of a composition as defined above, for giving the hair sheen, lightness, softness, a smooth feel and/or suppleness.
  • Another subject of the invention relates to a process for treating keratin materials, such as the hair, characterized in that it consists in applying, to said materials, a cosmetic composition according to the invention.
  • the term "keratin materials” is understood to mean the hair, the eyelashes, the eyebrows, the skin, the nails, the mucous membranes or the scalp, and more particularly the hair.
  • the term "sensitized hair” is understood to mean hair which has undergone physical external attacks (light, heat, waves, etc.), mechanical attacks (blowdrying, repeated combing or brushing, etc.) or chemical attacks (oxidation dyeing, bleaching, permanent waving, straightening, etc.).
  • the compositions according to the invention are particularly effective on hair sensitized by chemical attacks.
  • the term "at least one” will be understood to mean “one or more", i.e. one, two, three or more.
  • the term "insoluble compound” is intended to mean a compound which, at 25°C and at a concentration greater than or equal to 0.1 % by weight in water, does not form a transparent isotropic solution.
  • the term “non-volatile compound” is intended to mean a compound which, at ambient temperature (on average 25°C), is capable of remaining on the hair for several hours.
  • a non-volatile compound has in particular a vapour pressure, at ambient temperature (on average 25°C), of less than 2.66 Pa (0.02 mm of mercury), better still less than 0.13 Pa (0.001 mm of mercury).
  • amino 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. Amino silicones do not comprise any quaternary ammonium groups.
  • amino silicones different from the polydimethylsiloxanes (i) used in the cosmetic composition according to the present invention are chosen from the silicones of formula (I) below:
  • T is a hydrogen atom, or a phenyl, hydroxyl (-OH), or d-Cs alkyl, and preferably methyl, or d-Cs alkoxy, preferably methoxy, radical,
  • a denotes the number 0 or an integer from 1 to 3, and preferably 0,
  • b denotes 0 or 1 , and in particular 1 ,
  • n and n are numbers such that the sum (n + m) can range especially from 1 to 2000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to 1999 and in particular from 49 to 149, and for m to denote a number from 1 to 2000 and in particular from 1 to 10;
  • R 1 is a monovalent radical of formula -CqH2qL in which q is a number from 2 to 8, it being possible for one or more hydrogen atoms to be substituted with a hydroxyl group, and L is an optionally quaternized amino group chosen from the groups:
  • R 2 and R' 2 can denote a hydrogen atom, a phenyl, a benzyl, or a monovalent saturated hydrocarbon-based radical, for example a C1-C20 alkyl radical, and Q et Q " represents an anion such as, for example, fluoride, chloride, bromide or iodide.
  • amino silicones corresponding to the definition of formula (I) are chosen from the compounds corresponding to the formula below:
  • R, R' and R which may be identical or different, denote a C1-C4 alkyl radical, preferably CH 3 ; a C1-C4 alkoxy radical, preferably methoxy; or OH;
  • A represents a linear or branched, C3-C8 and preferably C3-C6 alkylene radical; m and n are integers dependent on the molecular weight and the sum of which is between 1 and 2000.
  • R, R' and R" which may be identical or different, represent a C1-C4 alkyl radical, preferably methyl, or a hydroxyl radical
  • A represents a d-Cs and preferably C3-C4 alkylene radical
  • m and n are such that the weight-average molecular weight of the compound is between 5000 and 500 000 approximately.
  • the compounds of this type are called "amodimethicone" in the CTFA dictionary.
  • R, R' and R" which may be identical or different, represent a C1-C4 alkoxy or hydroxyl radical, at least one of the radicals R or R" is an alkoxy radical and A represents a C3 alkylene radical.
  • the hydroxy/alkoxy molar ratio is preferably between 0.2/1 and 0.4/1 and advantageously equal to 0.3/1 .
  • m and n are such that the weight-average molecular weight of the compound is between 2000 and 10 6 . More particularly, n is between 0 and 999 and m is between 1 and 1000, the sum of n and m being between 1 and 1000. In this category of compounds, mention may be made, inter alia, of the product Belsil® ADM 652 sold by Wacker.
  • R and R" which are different, represent a C1-C4 alkoxy or hydroxyl radical
  • at least one of the radicals R or R" is an alkoxy radical
  • R' represents a methyl radical
  • A represents a C3 alkylene radical.
  • the hydroxy/alkoxy molar ratio is preferably between 1/0.8 and 1/1 .1 , and advantageously is equal to 1/0.95.
  • m and n are such that the weight- average molecular weight of the compound is between 2000 and 200 000. More particularly, n is between 0 and 999 and m is between 1 and 1000, the sum of n and m being between 1 and 1000.
  • amino silicones used in the composition in accordance with the invention preferably have general formula (III) below:
  • A denotes a C2-C8 and preferably C2-C6, better still C3, linear or branched alkylene radical
  • Ri and R 2 denote, independently of one another, a C1-C4 alkyl, preferably methyl, radical or a C1-C4 alkoxy, preferably methoxy, radical or a hydroxyl radical, m and n are numbers such that the weight-average molecular weight (Mw) is greater than or equal to 75 000.
  • radicals R1 are identical and denote a hydroxyl radical.
  • the viscosity of the amino silicone according to the invention is greater than 25 000 mm 2 /s measured at 25°C. More preferentially, the viscosity of the amino silicone is between 30 000 and 200 000 mm 2 /s at 25°C and even more preferentially between 50 000 and 150 000 mm 2 /s, measured at 25°C, and even better still from 70 000 to 120 000 mm 2 /s.
  • the viscosities of the silicones are, for example, measured according to standard "ASTM 445 Appendix C".
  • the cationic charge of the amino silicone according to the invention is less than or equal to 0.5 meq./g, preferably ranging from 0.01 to 0.1 meq./g and better still from 0.03 to 0.06 meq./g.
  • the amino silicone according to the invention has a weight-average molecular weight (Mw) ranging from 75 000 to 1 000 000 and even more preferentially ranging from 100 000 to 200 000.
  • the weight-average molecular weights of the amino silicones according to the invention are measured by gel permeation chromatography (GPC) at ambient temperature, as polystyrene equivalents.
  • the columns used are ⁇ styragel columns.
  • the eluent is THF and the flow rate is 1 ml/minute. 200 ⁇ of a solution containing 0.5% by weight of silicone in THF are injected. Detection is performed by refractometry and UV-metry.
  • a particularly preferred amino silicone corresponding to formula (III) is, for example, Dow Corning 2-8299® Cationic Emulsion from the company Dow Corning.
  • a product corresponding to the definition of formula (I) is in particular the polymer called "trimethylsilylamodimethicone" in the CTFA dictionary, corresponding to formula (IV) below:
  • n and m have the meanings given above in accordance with formula (II).
  • Such compounds are described, for example, in EP 95238; a compound of formula (III) is, for example, sold under the name Q2-8220 by the company OSI.
  • amino silicones according to the invention are quaternized amino silicones, and in particular:
  • R3 represents a d-ds alkyl radical, for example methyl
  • R4 represents a divalent hydrocarbon-based radical, in particular a d-ds alkylene radical
  • Q " is an anion, in particular chloride
  • R 7 which may be identical or different, represent a monovalent hydrocarbon- based radical containing from 1 to 8 carbon atoms, and in particular a d-d alkyl radical, for example methyl;
  • R 6 represents a divalent hydrocarbon-based radical, especially a d-ds alkylene radical or a divalent d-ds, and for example d-d, alkylenoxy radical linked to the Si via an SiC bond;
  • R 8 which may be identical or different, represent a hydrogen atom, a monovalent hydrocarbon-based radical containing from 1 to 18 carbon atoms, and in particular a d-C-18 alkyl radical, a d-ds alkenyl radical or a radical -R6-NHCOR7;
  • X- is an anion such as a halide ion, especially chloride, or an organic acid salt (acetate, etc.);
  • r represents a mean statistical value from 2 to 200 and in particular from 5 to 100.
  • R-i , R2, R3 and R 4 which may be identical or different, denote a Ci-C 4 alkyl radical or a phenyl group,
  • R 5 denotes a Ci-C 4 alkyl radical or a hydroxyl group
  • - n is an integer ranging from 1 to 5
  • - m is an integer ranging from 1 to 5
  • x is selected such that the amine number is between 0.01 and 1 meq/g.
  • the amino silicones of the invention are non-quaternized, i.e. they do not comprise a nitrogen atom with a permanent charge.
  • the silicones which are particularly preferred in accordance with the invention are polysiloxanes comprising amino groups, such as amodimethicones or trimethyl- silylamodimethicones, and in particular the compounds of formulae (II), (III) and (IV).
  • amino silicones of the invention are used, a particularly advantageous embodiment is their joint use with cationic and/or nonionic surfactants.
  • Emulsion DC 929 by the company Dow Corning, which comprises, besides amodimethicone, a cationic surfactant comprising a mixture of products corresponding to the formula:
  • R 5 denotes C-K-C22 alkenyl and/or alkyl radicals derived from tallow fatty acids, and known under the CTFA name tallowtrimonium chloride, in combination with a nonionic surfactant of formula: C9Hi 9-C6H4-(OC2H4)io-OH, known under the CTFA name Nonoxynol 10.
  • Use may also be made, for example, of the product sold under the name Cationic Emulsion DC 939 by the company Dow Corning, which comprises, besides amodimethicone, a cationic surfactant which is trimethylcetylammonium chloride and a nonionic surfactant of formula: Ci3H27-(OC2H 4 )i2-OH, known under the CTFA name Trideceth-12.
  • Cationic Emulsion DC 939 by the company Dow Corning
  • a cationic surfactant which is trimethylcetylammonium chloride
  • a nonionic surfactant of formula: Ci3H27-(OC2H 4 )i2-OH known under the CTFA name Trideceth-12.
  • the oil-in-water emulsion may comprise one or more surfactants.
  • the surfactants may be of any nature but are preferably cationic and/or nonionic.
  • the silicone particles in the emulsion have a volume-average diameter [D4.3] generally ranging from 10 nm to 1000 nanometres, preferably from 50 nm to 800 nanometres, more particularly from 100 nm to 600 nanometres and even more particularly from 200 nm to 500 nanometres. These particle sizes may be determined especially using a laser granulometer, for example the Malvern Mastersizer 2000 granulometer.
  • silicones can also be used in the form of emulsions or of microemulsions.
  • amino silicone(s) of formula (I) can represent from
  • 0.001 % to 20% by weight preferably from 0.01 % to 10% by weight and more particularly from 0.1 to 3% by weight, better still from 0.5 to 3% by weight, relative to the total weight of the final composition.
  • liquid fatty esters (ii) that can be used in the present invention are preferably monomeric. They are preferably nonionic and non-silicone.
  • liquid fatty esters is intended to mean an ester which is liquid at ambient temperature (25°C) and at atmospheric pressure (1 atm) and which results from a carboxylic acid and an alcohol, at least one of these two constituents containing at least 7 carbon atoms.
  • the alcohol which makes it possible to form the ester function is a monoalcohol
  • acyclic liquid fatty esters of a monoalcohol according to the invention are in particular chosen from:
  • the esters according to the invention are water-insoluble liquid esters.
  • the water-insoluble liquid carboxylic acid esters are insoluble in water at a concentration greater than or equal to 0.1 % by weight in water at 25°C, i.e. they do not form, under these conditions, a macroscopically isotropic transparent solution.
  • the total carbon number of the esters of the invention is generally greater than or equal to 10 and preferably less than 50 and more particularly less than 30.
  • liquid esters of a C3-C30 carboxylic acid and of a C1-C30 monoalcohol, at least one of the acid or of the alcohol being branched or unsaturated, are in particular chosen from esters of a C6-C24 carboxylic acid and of a C3-C20 alcohol.
  • esters according to the invention are in particular chosen from:
  • Use may also be made of esters of C4-C22 dicarboxylic or tricarboxylic acids and of C1-C22 monoalcohols.
  • Use may also be made of liquid esters of a branched carboxylic acid containing from 4 to 6 carbon atoms and of a monoalcohol containing from 8 to 26 carbon atoms.
  • the particular branched liquid esters preferably have the following formula: R1 COOR2 (VIII) in which:
  • R1 denotes a branched, optionally monohydroxylated or polyhydroxylated, hydrocarbon-based radical containing from 3 to 5 carbon atoms,
  • R2 denotes a linear or branched hydrocarbon-based radical containing from 12 to 26 carbon atoms, preferably containing from 16 to 22 carbon atoms.
  • R1 preferably denotes a branched alkyl radical containing from 3 to 5 carbon atoms, and more particularly a tert-butyl radical.
  • R2 preferably denotes a saturated or unsaturated alkyl radical containing 12 to 26 carbon atoms, which is more particularly branched and even more particularly chosen from tridecyl, isocetyl, isostearyl, octyldodecyl and isoarachidyl radicals.
  • the branched liquid esters that are particularly preferred in this variant are isostearyl neopentanoate, tridecyl neopentanoate, isocetyl neopentanoate and isoarachidyl neopentanoate.
  • the acid and the alcohol of the ester are saturated.
  • isopropyl palmitate 2-ethylhexyl palmitate, 2-octyldecyl palmitate, branched alkyl myristates such as isopropyl myristate, t-butyl myristate or 2-octyldodecyl myristate, hexyl isostearate, butyl isostearate, isobutyl stearate; 2-hexyldecyl laurate, isostearyl neopentanoate, tridecyl neopentanoate and isononyl isononanoate, and more particularly isopropyl palmitate, isopropyl myristate and isostearyl neopentanoate. Isopropyl myristate is quite particularly preferred.
  • the liquid fatty ester(s) of the invention can represent from 0.01 % to 50% by weight, preferably from 0.1 % to 25% by weight, and even more preferentially from 0.2% to 15% by weight, of the total weight of the composition.
  • non-amino polydimethylsiloxanes is intended to mean compounds different from the amino silicones of formula (I), and the repeating (R)(R')Si-0 groups of which are such that, when R and R' denote an alkyl group, then R and R' denote a methyl group.
  • the non-volatile, non-amino polydimethylsiloxanes that can be used in accordance with the invention preferably have a kinematic viscosity at 25°C greater than 350 cSt (mm 2 /s), even more preferentially a viscosity greater than 1000 cSt, and even more particularly greater than 10 000 cSt, better still greater than 50 000 cSt and preferably less than 10 000 000 cSt, better still less than 1 000 000 cSt, even better still less than 500 000 cSt.
  • the non-volatile, non-amino polydimethylsiloxanes that can be used in accordance with the invention are in particular polydimethylsiloxanes which are insoluble in the composition and can be in the form of oils, waxes, resins or gums. Mention may in particular be made of polydimethylsiloxanes with trimethylsilyl end groups having a viscosity of 10 x 10 "6 to 2.5 m 2 /s at 25°C and preferably 10 x 10 "5 to 1 m 2 /s. The viscosity of the silicones is measured, for example, at 25°C according to standard ASTM 445 Appendix C. Among these compounds, mention may be made, in a nonlimiting manner, of the following commercial products:
  • oils of the 200 series from the company Dow Corning such as, more particularly, DC200 with a viscosity of 60 000 cSt;
  • polydimethylsiloxanes with dimethylsilanol end groups such as the oils of the 48 series from the company Rhodia Chimie.
  • the polydimethylsiloxane gums are in particular polydimethylsiloxanes having high number-average molar masses of between 200 000 and 1 000 000, used alone or as a mixture in a solvent.
  • This solvent may be chosen from volatile silicones, polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffins, polyisobutylenes, methylene chloride, pentane, dodecane, tridecanes, or mixtures thereof.
  • Products that can be used more particularly are mixtures such as:
  • a polydimethylsiloxane gum with a cyclic silicone such as the product SF 1214 Silicone Fluid from the company General Electric, this product is a gum SF 30 corresponding to a dimethicone, having a number-average molecular weight of 500 000, solubilized in the SF 1202 Silicone Fluid oil corresponding to decamethylcyclopentasiloxane;
  • the product SF 1236 is a mixture of a gum SE 30 defined above with a viscosity of 20 m 2 /s and of an oil SF 96 with a viscosity of 5x10 "6 m 2 /s.
  • This product preferably comprises 15% of gum SE 30 and 85% of an oil SF 96.
  • all the polydimethylsiloxanes can be used as they are or in the form of solutions, emulsions, nanoemulsions or microemulsions.
  • the polydimethylsiloxanes that are particularly preferred in accordance with the invention are the polydimethylsiloxanes with trimethylsilyl end groups, such as the oils having a viscosity between 0.2 and 2.5 m 2 /s at 25°C, such as the oils of the DC200 series from Dow Corning, in particular the oil with a viscosity of 60 000 cSt or with a viscosity of 300 000 cSt, or the silicone sold under the name Belsil DM 300 000 by Wacker, and the polyalkylsiloxanes with dimethylsilanol end groups, such as dimethiconols.
  • the oils having a viscosity between 0.2 and 2.5 m 2 /s at 25°C such as the oils of the DC200 series from Dow Corning, in particular the oil with a viscosity of 60 000 cSt or with a viscosity of 300 000 cSt, or the silicone sold under the name Belsil DM 300 000 by
  • the non-volatile, non-amino polydimethylsiloxane(s) can represent from 0.01 % to 25% by weight, preferably from 0.1 % to 15% by weight, and even more preferentially from 1 % to 10% by weight, of the total weight of the final composition.
  • compositions according to the invention also comprise one or more agents that are beneficial to keratin materials, in particular the hair, such as in particular liquid fatty esters different from the fatty esters (ii), solid fatty esters of C1-C30 carboxylic acids and of monohydroxylated or polyhydroxylated C1-C30 alcohols, non-silicone cationic polymers, vegetable, animal, mineral or synthetic oils, waxes, ceramides or pseudoceramides, and mixtures thereof.
  • agents that are beneficial to keratin materials, in particular the hair such as in particular liquid fatty esters different from the fatty esters (ii), solid fatty esters of C1-C30 carboxylic acids and of monohydroxylated or polyhydroxylated C1-C30 alcohols, non-silicone cationic polymers, vegetable, animal, mineral or synthetic oils, waxes, ceramides or pseudoceramides, and mixtures thereof.
  • compositions of the invention can thus comprise one or more non-silicone cationic or amphoteric polymers in particular chosen from all those already known per se, in particular those described in Patent Application EP-A-0 337 354 and in the French Patent Applications FR-A-2 270 846, 2 383 660, 2 598 61 1 , 2 470 596 and 2 519 863.
  • the cationic polymers used generally have a molecular weight of between 500 and 5 x 10 6 approximately, and preferably between 10 3 and 3 x 10 6 approximately.
  • quaternized proteins or protein hydrolysates
  • polymers of the polyamine, polyaminoamide and polyquaternary ammonium type are known products.
  • the quaternized proteins or protein hydrolysates are in particular chemically modified polypeptides bearing quaternary ammonium groups at the end of the chain or grafted onto said chain.
  • Their molecular weight can range, for example, from 1500 to 10 000, and in particular from 2000 to 5000 approximately. Among these compounds, mention may be made especially of:
  • hydrolysates of collagen bearing trimethylammonium chloride and trimethylstearylammonium chloride groups called "steartrimonium hydrolyzed collagen” in the CTFA dictionary; - hydro lysates of proteins bearing, on the polypeptide chain, quaternary ammonium groups comprising at least one alkyl radical containing from 1 to 18 carbon atoms.
  • Croquat L Croquat M
  • Croquat S Crotein Q
  • quaternized proteins or hydrolysates are, for example, those sold by the company Inolex, under the name Lexein QX 3000.
  • quaternized vegetable proteins such as wheat, maize or soya proteins
  • quaternized wheat proteins mention may be made of those called “cocodimonium hydrolysed wheat protein", “lauridimonium hydrolysed wheat protein” or else "steardimonium hydrolysed wheat protein” in the CTFA dictionary.
  • polymers of polyamine, polyamidoamide and polyquaternary ammonium type that can be used in accordance with the present invention, and that can in particular be mentioned, are those described in French Patents No. 2 505 348 or 2 542 997. Among these polymers, mention may be made of:
  • R 3 and R 4 which may be identical or different, represent hydrogen or an alkyl group containing from 1 to 6 carbon atoms, and preferably methyl or ethyl;
  • R 5 which may be identical or different, denote a hydrogen atom or a radical CH 3 ;
  • A which may be identical or different, represent a linear or branched alkyl group containing from 1 to 6 carbon atoms, preferably 2 or 3 carbon atoms, or a hydroxyalkyl group containing from 1 to 4 carbon atoms;
  • R 6 , R7 and R 8 which may be identical or different, represent an alkyl group containing from 1 to 18 carbon atoms or a benzyl radical and preferably an alkyl group containing from 1 to 6 carbon atoms;
  • X denotes an inorganic or organic anion, such as a methosulphate anion or a halide such as chloride or bromide.
  • the copolymers of the family (1 ) may also contain one or more units deriving from comonomers which may be chosen from the family of acrylamides, methacrylamides, diacetone acrylamides, acrylamides and methacrylamides substituted on the nitrogen by lower alkyls (Ci-C 4 ), acrylic acids or methacrylic acids or esters thereof, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, and vinyl esters.
  • comonomers which may be chosen from the family of acrylamides, methacrylamides, diacetone acrylamides, acrylamides and methacrylamides substituted on the nitrogen by lower alkyls (Ci-C 4 ), acrylic acids or methacrylic acids or esters thereof, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, and vinyl esters.
  • Use may more particularly be made of a crosslinked acrylamide/methacryloyloxyethyltrimethylammonium chloride copolymer (20/80 by weight) in the form of a dispersion containing 50% by weight of said copolymer in mineral oil.
  • This dispersion is sold under the name Salcare ® SC 92 by the company BASF.
  • Use may also be made of a crosslinked methacryloyloxyethyl- trimethylammonium chloride homopolymer containing approximately 50% by weight of the homopolymer in mineral oil or in a liquid ester. These dispersions are sold under the names Salcare ® SC 95 and Salcare ® SC 96 by the company BASF.
  • Water-soluble polyaminoamides prepared in particular by polycondensation of an acidic compound with a polyamine; these polyaminoamides can be crosslinked with an epihalohydrin, a diepoxide, a dianhydride, an unsaturated dianhydride, a bisunsaturated derivative, a bis-halohydrin, a bisazetidinium, a bis- haloacyldiamine, a bis-alkyl halide or alternatively with an oligomer resulting from the reaction of a difunctional compound which is reactive with a bis-halohydrin, a bis-azetidinium, a bis-haloacyldiamine, a bis-alkyl halide, an epihalohydrin, a diepoxide or a bis-unsaturated derivative; the crosslinking agent being used in proportions ranging from 0.025 to 0.35 mol per amine group of the polyaminoamide; these polyaminoamides can
  • Polyaminoamide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation with difunctional agents Mention may be made, for example, of adipic acid/dialkylaminohydroxy- alkyldialkylenetriamine polymers in which the alkyl radical comprises from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl. Such polymers are especially described in French patent 1 583 363. Among these derivatives, mention may more particularly be made of the adipic acid/dimethylaminohydroxypropyl/diethylenetriamine polymers sold under the name Cartaretine F, F4 or F8 by the company Sandoz.
  • the molar ratio between the polyalkylene polyamine and the dicarboxylic acid is between 0.8: 1 and 1 .4: 1 ; the polyaminoamide resulting therefrom is reacted with epichlorohydrin in a molar ratio of epichlorohydrin relative to the secondary amine group of the polyaminoamide of between 0.5: 1 and 1 .8: 1 .
  • Such polymers are described in particular in US patents 3 227 615 and 2 961 347.
  • Polymers of this type are in particular sold under the name Hercosett 57 by the company Hercules Inc. or else under the name PD 170 or Delsette 101 by the company Hercules in the case of the adipic acid/epoxypropyl/diethylenetriamine copolymer.
  • 2 denotes a hydrogen atom or a methyl radical
  • R-io and R-n independently of one another, denote an alkyl group containing from 1 to 6 carbon atoms, a hydroxyalkyl group in which the alkyl group preferably contains 1 to 5 carbon atoms, or a lower (C1-C4) amidoalkyl group, or R-io and R-n can denote, together with the nitrogen atom to which they are attached, heterocyclic groups, such as piperidinyl or morpholinyl
  • Y " is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulphate, bisulphite, sulphate or phosphate.
  • R-io and R-n independently of one another, preferably denote an alkyl group containing from 1 to 4 carbon atoms.
  • polymers defined above mention may more particularly be made of the homopolymer of dimethyldiallylammonium chloride sold, for example under the name Merquat 100 by the company Nalco (and the low weight-average molecular weight homologues thereof) and the copolymers of diallyldimethylammonium chloride and of acrylamide sold, for example, under the name Merquat 550.
  • 6 which may be identical or different, represent aliphatic, alicyclic or arylaliphatic radicals containing from 1 to 20 carbon atoms or lower hydroxyalkylaliphatic radicals, or else R-
  • Ai and Bi represent polymethylene groups containing from 2 to 20 carbon atoms which may be linear or branched, and saturated or unsaturated, and which may contain, linked to or inserted in the main chain, one or more aromatic rings, or one or more oxygen or sulphur atoms or sulphoxide, sulphone, disulphide, amino, alkylamino, hydroxyl, quaternary ammonium, ureido, amide or ester groups, and X " denotes an anion derived from an inorganic or organic acid;
  • A-i , R-1 3 and R-15 can form, with the two nitrogen atoms to which they are attached, a piperazine ring; in addition, if Ai denotes a linear or branched, saturated or unsaturated alkylene or hydroxyalkylene radical, Bi can also denote a group (CH 2 ) n -CO-D-OC-(CH 2 )p- in which:
  • n and p which may be identical or different, are integers ranging from 2 to 20 approximately,
  • D denotes: a) a glycol residue of formula: -0-Z-0-, where Z denotes a linear or branched hydrocarbon-based radical or a group corresponding to one of the following formulae:
  • x and y denote an integer from 1 to 4, representing a defined and unique degree of polymerization or any number from 1 to 4 representing an average degree of polymerization;
  • a bis-secondary diamine residue such as a piperazine derivative
  • Y denotes a linear or branched hydrocarbon-based radical, or alternatively the divalent radical -CH 2 -CH 2 -S-S-CH 2 -CH 2 -;
  • X " is an anion such as chloride or bromide.
  • polymers of this type have a number-average molecular weight generally between 1000 and 100 000.
  • Polymers of this type are in particular described in French Patents 2 320 330, 2 270 846, 2 316 271 , 2 336 434 and 2 413 907 and US Patents 2 273 780, 2 375 853, 2 388 614, 2 454 547, 3 206 462, 2 261 002, 2 271 378, 3 874 870, 4 001 432, 3 929 990, 3 966 904, 4 005 193, 4 025 617, 4 025 627, 4 025 653, 4 026 945 and 4 027 020.
  • 8 , R19, R20 and R21 which may be identical or different, denote an alkyl or hydroxyalkyl radical containing from 1 to 4 carbon atoms approximately, r and s are integers ranging from 2 to 20 approximately, and X " is an anion derived from an inorganic or organic acid.
  • a compound of formula (XVI) that is particularly preferred is that for which R-
  • R 22 , R23, R24 and R25 which may be identical or different, represent a hydrogen atom or a methyl, ethyl, propyl, ⁇ -hydroxyethyl, ⁇ -hydroxypropyl or -CH 2 CH 2 (OCH 2 CH 2 ) P OH radical,
  • t and u which may be identical or different, are integers between 1 and 6, v is equal to 0 or to an integer between 1 and 34,
  • X denotes an anion such as a halide
  • A denotes a radical of a dihalide or preferably represents -CH 2 -CH 2 -O-CH 2 -
  • Cationic polysaccharides especially cationic celluloses and galactomannan gums.
  • cationic polysaccharides mention may be made more particularly of cellulose ether derivatives comprising quaternary ammonium groups, cationic cellulose copolymers or cellulose derivatives grafted with a water- soluble quaternary ammonium monomer and cationic galactomannan gums.
  • cellulose ether derivatives comprising quaternary ammonium groups are described in French Patent 1 492 597. These polymers are also defined in the CTFA dictionary as quaternary ammoniums of hydroxyethylcellulose that have reacted with an epoxide substituted with a trimethylammonium group.
  • Cationic cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer are described especially in US patent 4 131 576, such as hydroxyalkyl celluloses, for instance hydroxymethyl-, hydroxyethyl- or hydroxypropylcelluloses grafted, in particular, with a methacryloylethyltrimethylammonium, methacrylamidopropyltrimethylammonium or dimethyldiallylammonium salt.
  • the cationic galactomannan gums are described more particularly in US patents 3 589 578 and 4 031 307, in particular guar gums containing cationic trialkylammonium groups. Guar gums modified with a salt (e.g. chloride) of 2,3- epoxypropyltrimethylammonium are used, for example.
  • cationic polymers that may be used in the context of the invention are cationic proteins or cationic protein hydrolysates, polyalkyleneimines, in particular polyethyleneimines, polymers containing vinylpyridine or vinylpyridinium units, condensates of polyamines and of epichlorohydrin, quaternary polyureylenes and chitin derivatives.
  • quaternary cellulose ether derivatives such as the products sold under the name JR 400 by the company Amerchol, cyclopolymers, in particular homopolymers of a diallyldimethylammonium salt and copolymers of a diallyldimethylammonium salt and of acrylamide, in particular the chlorides, sold under the names Merquat 550 and Merquat S by the company Nalco, cationic polysaccharides, and more particularly the guar gums modified with 2,3-epoxypropyltrimethylammonium chloride sold, for example, under the name Jaguar C13S by the company Rhodia Chimie, optionally crosslinked homopolymers and copolymers of a (meth)acryloyloxyethyltrimethylammonium salt, sold in particular by the company BASF as a 50% solution in mineral oil under the trade names Salcare SC92 (cross
  • the additional beneficial agents can represent from 0.001 % to 20% by weight, preferably from 0.01 % to 10% by weight and more particularly from 0.05 to 5% by weight, relative to the total weight of the final composition.
  • the compositions of the invention also advantageously contain one or more surfactants which are generally present in an amount between 0.01 % and 50% by weight approximately, preferably between 0.1 % and 40% and even more preferentially between 0.5% and 30%, relative to the total weight of the composition.
  • This surfactant or these surfactants can be chosen from anionic, amphoteric, nonionic and cationic surfactants, or mixtures thereof.
  • the surfactants suitable for implementing the present invention are in particular the following:
  • anionic surfactant is intended to mean a surfactant comprising, as ionic or ionizable groups, only anionic groups. These anionic groups are preferably chosen from the groups C0 2 H, C0 2 " , S0 3 H, S0 3 " , OS0 3 H, OS0 3 " , 0 2 P0 2 H, 0 2 P0 2 H “ and 0 2 P0 22 " .
  • the anionic surfactant(s) that may be used in the compositions of the invention is (are) in particular chosen from alkyl sulphates, alkyl ether sulphates, alkylamidoether sulphates, alkylarylpolyether sulphates, monoglyceride sulphates, alkyl sulphonates, alkylamide sulphonates, alkylaryl sulphonates, alpha-olefin sulphonates, paraffin sulphonates, alkyl sulphosuccinates, alkyl ether sulphosuccinates, alkylamide sulphosuccinates, alkyl sulphoacetates, acyl sarcosinates, acyl glutamates, alkyl sulphosuccinamates, acyl isethionates and N- acyltaurates, salts of alkyl monoesters of polyglycoside-polycarboxylic acids,
  • Some of these compounds may be oxyethylenated and then preferably comprise from 1 to 50 ethylene oxide units.
  • the salts of C6-C 24 alkyl monoesters of polyglycoside-polycarboxylic acids can be chosen from C6-C 24 alkyl polyglycoside citrates, C6-C 24 alkyl polyglycoside- tartrates and C6-C 24 alkyl polyglycoside-sulphosuccinates.
  • anionic surfactant(s) (i) When the anionic surfactant(s) (i) is (are) in salt form, it (they) is (are) not in the form of zinc salts, and it (they) can be chosen from the alkali metal salts, such as the sodium or potassium salt and preferably the sodium salt, the ammonium salts, the amine salts and in particular amino alcohol salts, and the alkaline-earth metal salts, such as the magnesium salt.
  • the alkali metal salts such as the sodium or potassium salt and preferably the sodium salt, the ammonium salts, the amine salts and in particular amino alcohol salts, and the alkaline-earth metal salts, such as the magnesium salt.
  • amino alcohol salts By way of example of amino alcohol salts, mention may in particular be made of the mono-, di- and triethanolamine salts, the mono-, di- or triisopropanolamine salts, and the 2-amino-2-methyl-1 -propanol, 2-amino-2-methyl-1 ,3-propanediol and tris(hydroxymethyl)aminomethane salts.
  • Alkali metal or alkaline-earth metal salts and in particular sodium or magnesium salts, are preferably used.
  • Use is preferably made of (C6-C 24 )alkyl sulphates and (C6-C 24 )alkyl ether sulphates, which are optionally oxyethylenated, comprising from 2 to 50 ethylene oxide units, and mixtures thereof, in particular in the form of alkali metal salts, alkaline-earth metal salts, ammonium salts or amino alcohol salts.
  • the anionic surfactant(s) is (are) chosen from (Cio-C 2 o)alkyl ether sulphates, and in particular sodium lauryl ether sulphate comprising 2.2 mol of ethylene oxide.
  • the amount of the anionic surfactant(s) preferably ranges from 0.1 to 50% by weight, even better still from 4 to 30% by weight, relative to the total weight of the composition.
  • Nonionic surfactants are themselves also compounds that are well known per se (see especially in this regard the "Handbook of Surfactants” by M.R. Porter, published by Blackie & Son (Glasgow and London), 1991 , pp. 1 16-178). Thus, they can in particular be chosen from (nonlimiting list) alcohols, alpha-diols and alkylphenols, these compounds being polyethoxylated, polypropoxylated or polyglycerolated, and having at least one fatty chain containing for example 8 to 18 carbon atoms, it being possible for the number of ethylene oxide or propylene oxide groups to range in particular from 2 to 50 and for the number of glycerol groups to range in particular from 2 to 30.
  • copolymers of ethylene oxide and of propylene oxide, condensates of ethylene oxide and of propylene oxide with fatty alcohols polyethyoxylated fatty amides preferably having from 2 to 30 mol of ethylene oxide, polyglycerolated fatty amides comprising on average 1 to 5 glycerol groups and in particular 1.5 to 4; polyethoxylated fatty amines preferably having 2 to 30 mol of ethylene oxide; oxyethylenated fatty acid esters of sorbitan having from 2 to 30 mol of ethylene oxide; fatty acid esters of sucrose, fatty acid esters of polyethylene glycol, alkylpolyglycosides, N-alkylglucamine derivatives, and amine oxides, such as (C-io- Cu)alkylamine oxides or N-acylaminopropylmorpholine oxides.
  • alkylpolyglycosides constitute nonionic surfactants
  • amphoteric or zwitterionic surfactant(s) that can be used in the present invention may in particular be derivatives of secondary or tertiary aliphatic amines, which are optionally quaternized, in which the aliphatic group is a linear or branched chain containing from 8 to 22 carbon atoms, said amine derivatives containing at least one anionic group such as, for example, a carboxylate, sulphonate, sulphate, phosphate or phosphonate group.
  • Ra represents a C10-C30 alkyl or alkenyl group derived from an acid
  • Ra-COOH preferably present in hydrolysed coconut oil, or a heptyl, nonyl or undecyl group,
  • Rb represents a ⁇ -hydroxyethyl group
  • Rc represents a carboxymethyl group
  • X represents the group -CH 2 -COOH, CH 2 -COOZ', -CH 2 CH 2 -COOH or -CH 2 CH 2 - COOZ', or a hydrogen atom
  • Y' represents -COOH, -COOZ, or the group -CH 2 -CHOH-S0 3 H or -CH 2 -CHOH-
  • Z' represents an ion derived from an alkali metal or alkaline-earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine,
  • Ra' represents a C10-C30 alkyl or alkenyl group of an acid Ra'-COOH preferably present in hydrolysed coconut oil or hydrolysed linseed oil, an alkyl group, in particular a C17 alkyl group, and its isoform, or an unsaturated C17 group.
  • cocoamphodiacetate sold by the company Rhodia under the trade name Miranol ® C2M Concentrate.
  • amphoteric or zwitterionic surfactants mentioned above use is preferably made of (C8-C 20 alkyl)betaines such as cocoylbetaine, (C8-C 20 alkyl)amido(C 2 -C8 alkyl)betaines such as cocoylamidopropylbetaine, and mixtures thereof. More preferentially, the amphoteric or zwitterionic surfactant(s) is (are) chosen from cocoylamidopropylbetaine and cocoylbetaine.
  • the amount of the amphoteric or zwitterionic surfactant(s) is preferably in the range from 0.01 % to 20% by weight, even better still from 0.5% to 10% by weight, relative to the total weight of the composition.
  • the cationic surfactants can be chosen from optionally polyoxyalkylenated primary, secondary or tertiary fatty amine salts, quaternary ammonium salts, and mixtures thereof.
  • the groups R 8 to R-n which may be identical or different, each represent a linear or branched aliphatic group containing from 1 to 30 carbon atoms, or an aromatic group such as aryl or alkylaryl, at least one of the groups R 8 to R-n containing from 8 to 30 carbon atoms, preferably from 12 to 24 carbon atoms.
  • the aliphatic groups may comprise heteroatoms such as, in particular, oxygen, nitrogen, sulphur and halogens.
  • the aliphatic groups are chosen, for example, from C1-C30 alkyl, C1-C30 alkoxy, polyoxy(C2-C6)alkylene, C1-C30 alkylamide, (Ci2-C22)alkylamido(C2-C6)alkyl, (C12- C22)alkyl acetate, C1-C30 hydroxyalkyl groups, X " is an anion chosen from the group of halides, phosphates, acetates, lactates, (Ci-C 4 )alkyl sulfates, and (C-i- C 4 )alkyl- or (Ci-C 4 )alkylarylsulfonates.
  • tetraalkylammonium chlorides such as, for example, dialkyldimethyl- ammonium or alkyltrimethylammonium chlorides in which the alkyl group contains approximately from 12 to 22 carbon atoms, in particular behenyltrimethyl- ammonium, distearyldimethylammonium, cetyltrimethylammonium or benzyl- dimethylstearylammonium chlorides, or alternatively, on the other hand, distearoylethylhydroxyethylmethylammonium methosulphate, dipalmitoylethyl- hydroxyethylammonium methosulphate or distearoylethylhydroxyethylammonium methosulphate, or else finally, palmitylamidopropyltrimethylammonium chloride or the stearamidopropyldimethyl(myristyl acetate)
  • R-12 represents an alkenyl or alkyl group containing from 8 to 30 carbon atoms, for example tallow fatty acid derivatives
  • R-13 represents a hydrogen atom, a Ci-C 4 alkyl group or an alkenyl or alkyl group containing from 8 to 30 carbon atoms
  • RH represents a Ci-C 4 alkyl group
  • R-15 represents a hydrogen atom or a Ci-C 4 alkyl group
  • X " is an anion chosen from the group of halides, phosphates, acetates, lactates, (Ci-C 4 )alkyl sulphates, and (Ci-C 4 )alkyl- or (C-i- C 4 )alkylarylsulphonates.
  • R-12 and Ri 3 preferably denote a mixture of alkyl or alkenyl groups containing from 12 to 21 carbon atoms, for example tallow fatty acid derivatives, Ru denotes a methyl group, and R-
  • a product is, for example, sold under the name Rewoquat ® W 75 by the company Rewo;
  • 6 denotes an alkyl group containing approximately from 16 to 30 carbon atoms, which is optionally hydroxylated and/or interrupted with one or more oxygen atoms
  • 7 is chosen from hydrogen, an alkyl group containing from 1 to 4 carbon atoms or a group -(CH 2 ) 3 -N + (Ri6a)(Ri7a)(Ri 8a);
  • Ri ea, Ri 7a, Ri ea, Ri e, Ri 9, R20 and R21 which may be identical or different, are chosen from hydrogen and an alkyl group containing from 1 to 4 carbon atoms
  • X " is an anion chosen from the group of halides, acetates, phosphates, nitrates, (Ci -C 4 )alkyl sulphates, and (Ci -C 4 )alkyl- or (Ci -C 4 )alkylarylsulphonates, in particular methyl sulphate and eth
  • R22 is chosen from C1-C6 alkyl groups and C1 -C6 hydroxyalkyl or dihydroxyalkyl groups,
  • R23 is chosen from:
  • radicals R27 which are linear or branched, saturated or unsaturated C1 -C22 hydrocarbon-based radicals
  • R25 is chosen from: - the group — C—
  • radicals R29 which are linear or branched, saturated or unsaturated C1-C6 hydrocarbon-based radicals
  • R24, R26 and R28 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C7-C21 hydrocarbon-based groups;
  • r, s and t which may be identical or different, are integers ranging from 2 to 6, r1 and t1 , which may be identical or different, are equal to 0 or 1 ,
  • y is an integer ranging from 1 to 10,
  • x and z which may be identical or different, are integers ranging from 0 to 10
  • X " is a simple or complex, organic or inorganic anion
  • the alkyl groups R22 may be linear or branched, and more particularly linear.
  • R22 denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl group, and more particularly a methyl or ethyl group.
  • the sum x + y + z equals from 1 to 10.
  • R23 is a hydrocarbon-based group R27, it may be long and contain from 12 to 20 carbon atoms, or short and contain from 1 to 3 carbon atoms.
  • R25 is a hydrocarbon-based group R29, it preferably contains 1 to 3 carbon atoms.
  • R 24 , R26 and R 2 8 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C11-C21 hydrocarbon-based groups, and more particularly from linear or branched, saturated or unsaturated C11-C21 alkyl and alkenyl groups.
  • x and z which may be identical or different, equal 0 or 1.
  • y is equal to 1 .
  • r, s and t which may be identical or different, equal 2 or 3, and even more particularly are equal to 2.
  • the anion X " is preferably a halide, preferably chloride, bromide or iodide, a (C-i- C 4 )alkyl sulphate, or a (Ci-C 4 )alkyl- or (Ci-C 4 )akylarylsulphonate.
  • a halide preferably chloride, bromide or iodide, a (C-i- C 4 )alkyl sulphate, or a (Ci-C 4 )alkyl- or (Ci-C 4 )akylarylsulphonate.
  • methanesulphonate, phosphate, nitrate, tosylate an anion derived from an organic acid, such as acetate or lactate, or any other anion that is compatible with the ammonium containing an ester function.
  • anion X " is even more particularly chloride, methyl sulphate or ethyl sulphate. Use is more particularly made, in the composition according to the invention, of the ammonium salts of formula (XXIII) in which:
  • R22 denotes a methyl or ethyl group
  • - R25 is chosen from:
  • R24, R26 and R 2 8 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C13-C17 hydrocarbon-based groups, and preferably from linear or branched, saturated or unsaturated C13-C17 alkyl and alkenyl groups
  • hydrocarbon-based groups are advantageously linear.
  • acyl groups preferably contain 14 to 18 carbon atoms and originate more particularly from a vegetable oil such as palm oil or sunflower oil. When the compound contains several of the salts, in particular diacyloxyethyldimethylammonium, diacyloxyethylhydroxy- ethylmethylammonium, monoacyloxyethyldihydroxyethylmethylammonium, triacyl- oxyethylmethylammonium and monoacyloxyethylhydroxyethyldimethylammonium chloride, diacyloxyethyldimethylammonium, diacyloxyethylhydroxyethylmethyl- ammonium, monoacyloxyethyldihydroxyethylmethylammonium, triacyloxyethyl- methylammonium and monoacyloxyethylhydroxyethyldimethylammonium methylsulphate, and mixtures thereof.
  • the acyl groups preferably contain 14 to 18 carbon atoms and originate more
  • This esterification is followed by a quaternization by means of an alkylating agent such as an alkyl halide, preferably methyl or ethyl halide, a dialkyl sulfate, preferably methyl or ethyl sulfate, methyl methanesulfonate, methyl para-toluenesulfonate, glycol chlorohydrin or glycerol chlorohydrin.
  • an alkylating agent such as an alkyl halide, preferably methyl or ethyl halide, a dialkyl sulfate, preferably methyl or ethyl sulfate, methyl methanesulfonate, methyl para-toluenesulfonate, glycol chlorohydrin or glycerol chlorohydrin.
  • Such compounds are, for example, sold under the names Dehyquart ® by the company Henkel, Stepanquat ® by the company Stepan, Noxamium ® by the company Ceca or Rewoquat ® WE 18 by the company Rewo-Witco.
  • composition according to the invention may contain, for example, a mixture of quaternary ammonium salts of mono-, di- and triesters with a weight majority of diester salts.
  • ammonium salts containing at least one ester function described in Patents US-A-4 874 554 and US-A-4 137 180, can also be used.
  • Use may also be made of behenoylhydroxypropyltrimethylammonium chloride sold by the company KAO under the name Quartamin BTC 131 .
  • the ammonium salts containing at least one ester function contain two ester functions.
  • the cationic surfactants that may be present in the composition according to the invention, it is more particularly preferred to choose the cetyltrimethylammonium, behenyltrimethylammonium and dipalmitoylethylhydroxy- ethylmethylammonium salts, and mixtures thereof, and more particularly behenyl- trimethylammonium chloride, cetyltrimethylammonium chloride, dipalmitoylethyl- hydroxyethylammonium methosulphate, and mixtures thereof.
  • the amount of the cationic surfactant(s) preferably ranges from 0.01 % to 20% by weight and even better still from 0.2% to 10% by weight, relative to the total weight of the composition.
  • compositions in accordance with the invention use may be made of mixtures of surfactants and in particular mixtures of anionic surfactants, mixtures of anionic surfactants and amphoteric, cationic or nonionic surfactants, and mixtures of cationic surfactants with nonionic or amphoteric surfactants.
  • composition of the invention may also contain one or more additives chosen from thickeners, anti-dandruff or anti-seborrheic agents, fragrances, hydroxy acids, electrolytes, preservatives, silicone or non-silicone sunscreens, vitamins, provitamins such as panthenol, anionic or nonionic polymers, proteins, protein hydrolysates, 18-methyleicosanoic acid, fluoro or perfluoro oils, fatty amines, fatty acids and derivatives thereof, fatty alcohols, and any other additive conventionally used in the cosmetics field which does not affect the properties of the compositions according to the invention.
  • additives chosen from thickeners, anti-dandruff or anti-seborrheic agents, fragrances, hydroxy acids, electrolytes, preservatives, silicone or non-silicone sunscreens, vitamins, provitamins such as panthenol, anionic or nonionic polymers, proteins, protein hydrolysates, 18-methyleicosanoic acid,
  • compositions in accordance with the invention can also contain up to 5% of pearlescent agents or opacifiers well known in the prior art, such as, for example, sodium or magnesium palmitates, sodium or magnesium stearates and hydroxy- stearates, acylated fatty-chain derivatives, such as ethylene glycol monostearates or distearates or polyethylene glycol monostearates or distearates, fatty-chain ethers, such as, for example, distearyl ether or 1 -(hexadecyloxy)-2-octadecanol, fatty alcohols, in particular stearyl, cetyl and behenyl alcohols, and mixtures thereof.
  • pearlescent agents or opacifiers well known in the prior art, such as, for example, sodium or magnesium palmitates, sodium or magnesium stearates and hydroxy- stearates, acylated fatty-chain derivatives, such as ethylene glycol monostearates or distear
  • compositions can comprise a physiologically, and in particular cosmetically, acceptable medium.
  • the physiologically, and in particular cosmetically, acceptable medium can be made up solely of water, or of a mixture of water and at least one cosmetically acceptable solvent, such as a C1 -C4 lower alcohol, for instance ethanol, isopropanol, tert-butanol or n-butanol; polyols such as propylene glycol, or polyol ethers.
  • a cosmetically acceptable solvent such as a C1 -C4 lower alcohol, for instance ethanol, isopropanol, tert-butanol or n-butanol
  • polyols such as propylene glycol, or polyol ethers.
  • the composition comprises from 50 to 95% by weight of water, relative to the total weight of the composition, and more particularly from 60 to 90% by weight.
  • compositions according to the invention have a final pH which is generally between 3 and 10. Preferably, this pH is between 4 and 8 and more particularly from 4 to 6.
  • the adjustment of the pH to the desired value can be carried out conventionally by adding a base (organic or inorganic) to the composition, for example aqueous ammonia or a primary, secondary or tertiary (poly)amine such as monoethanolamine, diethanolamine, triethanolamine, isopropanolamine or 1 ,3- propanediamine, or else by adding an inorganic or organic acid, preferably a carboxylic acid such as, for example, citric acid.
  • a base organic or inorganic
  • a primary, secondary or tertiary (poly)amine such as monoethanolamine, diethanolamine, triethanolamine, isopropanolamine or 1 ,3- propanediamine
  • an inorganic or organic acid preferably a carboxylic acid such as, for example, citric acid.
  • compositions in accordance with the invention can be more particularly used for washing or treating keratin materials such as the hair, the skin, the eyelashes, the eyebrows, the nails, the lips or the scalp, and more particularly the hair.
  • the compositions according to the invention are generally used as products in particular for washing, caring for, conditioning or retaining the form of the hairstyle or shaping keratin materials such as the hair.
  • compositions of the invention can more particularly be in the form of a shampoo, a leave-in or rinse-out conditioner, permanent-waving, straightening, dyeing or bleaching compositions, or else in the form of compositions to be applied before or after dyeing, bleaching, permanent-waving or straightening, or else between the two steps of a permanent-waving or straightening operation.
  • compositions are washing and foaming compositions for the hair and/or the skin.
  • compositions according to the invention are foaming detergent compositions such as shampoos, shower gels and bubble baths, or makeup- removing products.
  • the compositions comprise at least one or more detergent surfactants.
  • the surfactant(s) may then be without distinction chosen, alone or as a mixture, from anionic, amphoteric and nonionic surfactants, in particular as defined above.
  • anionic, amphoteric and nonionic surfactants in particular as defined above.
  • use is preferably made of at least one or more anionic surfactants or mixtures of at least one or more anionic surfactants and of at least one or more amphoteric surfactants or of at least one or more nonionic surfactants.
  • a particularly preferred mixture is a mixture comprising at least one or more anionic surfactants and at least one or more amphoteric surfactants.
  • Use is preferably made of an anionic surfactant chosen from sodium, triethanolamine or ammonium (Ci2-Cu)alkyl sulphates, oxyethylenated sodium, triethanolamine or ammonium (Ci2-Cu)alkyl ether sulphates comprising 2.2 mol of ethylene oxide, sodium cocoyl isethionate and sodium alpha-(Cu-Ci6)olefin sulphonate, and mixtures thereof with:
  • an amphoteric surfactant such as the amine derivatives known as disodium cocoamphodipropionate or disodium cocoamphopropionate that are sold in particular by the company Rhodia Chimie under the trade name Miranol C2M CONC as an aqueous solution containing 38% of active material, or under the name Miranol C32;
  • an amphoteric surfactant of zwitterionic type such as alkylbetaines, in particular the cocobetaine sold under the name Dehyton AB 30 as an aqueous solution containing 32% of AM, by the company Cognis, and the cocoamidopropyl- betaine sold in particular by Goldschmidt under the name Tegobetaine F50.
  • the minimum amount of surfactant is then that which is just sufficient to confer a satisfactory foaming and/or detergent power on the final composition.
  • the detergent surfactant can represent from 3% to 30% by weight, preferably from 6% to 25% by weight, and even more preferentially from 8% to 20% by weight, of the total weight of the final composition.
  • the foaming power of the compositions according to the invention is generally greater than 75 mm; preferably greater than 100 mm measured according to the modified Ross-Miles method (NF T 73-404/ISO696).
  • the modifications of the method are the following:
  • the measurement is carried out at the temperature of 22°C with osmosed water.
  • the concentration of the solution is 2 g/l.
  • the height of the drop is 1 m.
  • the amount of composition which drops is 200 ml. These 200 ml of composition fall into a graduating cylinder having a diameter of 50 mm and containing 50 ml of the test composition.
  • the measurement is carried out 5 minutes after the flow of the composition is stopped.
  • compositions of the invention when the composition is in the form of a care composition such as an optionally rinse-out conditioner, it advantageously comprises one or more cationic surfactants, the concentration of said surfactants generally ranging from 0.1 to 10% by weight and preferably from 0.5 to 5% by weight, relative to the total weight of the composition.
  • the compositions of the invention can also be in the form of permanent-waving, straightening, dyeing or bleaching compositions, or else in the form of compositions which are rinse-out, to be applied before or after dyeing, bleaching, permanent-waving or straightening or else between the two steps of a permanent- waving or straightening operation.
  • compositions according to the invention can be in the form of aqueous or aqueous-alcoholic skincare and/or haircare lotions.
  • the cosmetic compositions according to the invention can be in the form of a gel, a milk, a cream, an emulsion, a thickened lotion or a mousse, and be used for the skin, the nails, the eyelashes, the lips and more particularly the hair.
  • compositions can be packaged in various forms, in particular in vaporizers, pump-dispenser bottles or in aerosol or nonaerosol containers so as to apply the composition in vaporized form or in the form of a mousse.
  • Such packaging forms are indicated, for example, when it is desired to obtain a spray, a lacquer or a mousse for treating the hair.
  • a subject of the invention is also a process for treating keratin materials such as the skin or the hair, characterized in that it consists in applying, to the keratin materials, a cosmetic composition as defined above, and then in optionally rinsing with water after an optional leave-in time.
  • AM means active material
  • This composition is applied to the hair as a leave-in conditioner.
  • composition according to the invention brings sheen and disentangling, but also smoothness and liveliness to the hair, in particular on sensitized hair.
  • This composition is applied to hair as a leave-in conditioner.
  • composition according to the invention brings sheen, smoothness and styling, but also liveliness and disentangling to the hair, in particular on sensitized hair.
  • This composition is applied to hair as a leave-in conditioner.
  • composition according to the invention brings sheen, smoothness and styling, but also liveliness and disentangling to the hair, in particular on sensitized hair.
  • the following leave-in spray care composition is prepared:
  • the following shampoo composition is prepared:
  • the following shampoo composition is prepared:
  • the following rinse-out conditioner composition is prepared:
  • the following rinse-out conditioner composition is prepared:
  • the following post-dye rinse-out care composition is prepared:

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Abstract

The invention relates to novel cosmetic compositions comprising: (i) -one or more non-volatile, non-amino polydimethylsiloxanes, (ii) -one or more acyclic liquid fatty esters of a monoalcohol, and (iii) -one or more amino silicones different from the polysiloxanes (i) and chosen from the compounds corresponding to formula (I) below: (R1)a(T)3-a-Si[OSi(T)2]n-[OSi(T)b(R1)2-b]m-OSi(T)3-a-(R1)a The compositions are used in particular for washing and/or conditioning keratin materials such as the hair or the skin.

Description

COSMETIC COMPOSITION CONTAINING A NON-AMINO SILICONE, A LIQUID FATTY ESTER AND AN AMINO SILICONE, PROCESS AND USE The present invention relates to novel cosmetic compositions comprising one or more non-amino silicones, one or more particular liquid fatty esters and one or more particular amino silicones.
It is well known that hair which has been sensitized (i.e. damaged and/or embrittled) to varying degrees under the action of atmospheric agents or under the action of mechanical or chemical treatments, such as dyeing, bleaching and/or permanent-waving, is often difficult to disentangle and to style, and lacks softness.
It has already been recommended to use conditioners, in particular cationic or amphoteric polymers, fatty acid esters or volatile or non-volatile non-amino silicones in compositions for washing or caring for keratin materials such as the hair, in order to facilitate disentangling of the hair and to give it softness and manageability. However, the cosmetic advantages mentioned above are also unfortunately accompanied, on dried hair, by certain cosmetic effects considered to be undesirable, namely lankness of the hairstyle (lack of lightness of the hair) and lack of smoothness (hair not uniform from the root to the end). Amino silicones are generally used in cosmetic compositions as conditioners for improving the softness and the disentangling of the hair. However, it has been noted that, owing to their strong affinity to the hair, some of these amino silicones become deposited thereon to a large extent during repeated use, and lead to adverse effects such as an unpleasant laden feel, stiffening of the hair and interfibre adhesion which has an effect on styling. These drawbacks are accentuated in the case of fine hair, which lacks liveliness and body. Combinations of particular amino silicones, oils comprising ester functions and non-amino silicones are also known in document WO2009/059455. However, these combinations are not entirely satisfactory in particular in terms of sheen, smoothness and softness of the hair. It was therefore necessary to develop a cosmetic composition, in particular a detergent composition, especially a shampoo, which has a satisfactory aesthetic appearance, which is stable and which makes it possible to obtain good cosmetic performance on the keratin materials, namely in particular the hair and the scalp, and more particularly sensitized hair.
The applicant has now discovered that the combination of a non-volatile, non- amino insoluble silicone, of a particular amino silicone and of a particular liquid fatty ester makes it possible to remedy these drawbacks. Indeed, it has been noted that the use of the compositions of the present invention makes it possible to obtain, on keratin materials, in particular the hair, very good cosmetic properties particularly in terms of lightness, disentangling, smooth feel, body and sheen. It has also been noted that the compositions of the invention make it possible to obtain dried hair that looks generally smoother.
When the compositions comprise foaming surfactants, their foaming properties, in particular the initiation of foam, are not degraded.
In addition, the compositions rinse out easily.
The compositions of the invention applied to the skin, in particular in the form of a bubble bath or of a shower gel, give an improvement in the softness of the skin. Thus, according to the present invention, novel cosmetic compositions are now proposed, comprising:
(i) - one or more non-volatile, non-amino polydimethylsiloxanes,
(ii) - one or more acyclic liquid fatty esters of a monoalcohol, and
(iii) - one or more particular amino silicones.
A subject of the invention is also the use of a composition as defined above, for giving the hair sheen, lightness, softness, a smooth feel and/or suppleness.
Another subject of the invention relates to a process for treating keratin materials, such as the hair, characterized in that it consists in applying, to said materials, a cosmetic composition according to the invention.
According to the present invention, the term "keratin materials" is understood to mean the hair, the eyelashes, the eyebrows, the skin, the nails, the mucous membranes or the scalp, and more particularly the hair.
The various subjects of the invention will now be detailed. All the meanings and definitions of the compounds used in the present invention given below are valid for all of the subjects of the invention.
According to the present invention, the term "sensitized hair" is understood to mean hair which has undergone physical external attacks (light, heat, waves, etc.), mechanical attacks (blowdrying, repeated combing or brushing, etc.) or chemical attacks (oxidation dyeing, bleaching, permanent waving, straightening, etc.). The compositions according to the invention are particularly effective on hair sensitized by chemical attacks. The term "at least one" will be understood to mean "one or more", i.e. one, two, three or more.
For the purpose of the present invention, the term "insoluble compound" is intended to mean a compound which, at 25°C and at a concentration greater than or equal to 0.1 % by weight in water, does not form a transparent isotropic solution. For the purpose of the present invention, the term "non-volatile compound" is intended to mean a compound which, at ambient temperature (on average 25°C), is capable of remaining on the hair for several hours. A non-volatile compound has in particular a vapour pressure, at ambient temperature (on average 25°C), of less than 2.66 Pa (0.02 mm of mercury), better still less than 0.13 Pa (0.001 mm of mercury).
According to the invention, the term "amino 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. Amino silicones do not comprise any quaternary ammonium groups.
The amino silicones different from the polydimethylsiloxanes (i) used in the cosmetic composition according to the present invention are chosen from the silicones of formula (I) below:
( )a(T)3-a-Si[OSi(T)2]n-[OSi(T)b(R1)2-b]m-OSi(T)3-a-( 1)a (I) in which,
T is a hydrogen atom, or a phenyl, hydroxyl (-OH), or d-Cs alkyl, and preferably methyl, or d-Cs alkoxy, preferably methoxy, radical,
a denotes the number 0 or an integer from 1 to 3, and preferably 0,
b denotes 0 or 1 , and in particular 1 ,
m and n are numbers such that the sum (n + m) can range especially from 1 to 2000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to 1999 and in particular from 49 to 149, and for m to denote a number from 1 to 2000 and in particular from 1 to 10;
R1 is a monovalent radical of formula -CqH2qL in which q is a number from 2 to 8, it being possible for one or more hydrogen atoms to be substituted with a hydroxyl group, and L is an optionally quaternized amino group chosen from the groups:
-N(R2)-CH2-CH2-N(R'2)2;
-N(R2)2;
-N+(R2)3Q-;
-N+(R2) (H)2Q";
-N+(R2)2HQ";
-N(R2)-CH2-CH2-N+(R'2)(H)2Q", in which R2 and R'2 can denote a hydrogen atom, a phenyl, a benzyl, or a monovalent saturated hydrocarbon-based radical, for example a C1-C20 alkyl radical, and Q et Q" represents an anion such as, for example, fluoride, chloride, bromide or iodide.
In particular, the amino silicones corresponding to the definition of formula (I) are chosen from the compounds corresponding to the formula below:
CH3 †H3 R' CH,
R SSii-— 0 - - Si - Si 0— Si— R"
CH3 CH3 A
NH
(CH2)2
m
NhL
(II)
in which R, R' and R", which may be identical or different, denote a C1-C4 alkyl radical, preferably CH3; a C1-C4 alkoxy radical, preferably methoxy; or OH; A represents a linear or branched, C3-C8 and preferably C3-C6 alkylene radical; m and n are integers dependent on the molecular weight and the sum of which is between 1 and 2000. According to a first possibility, R, R' and R", which may be identical or different, represent a C1-C4 alkyl radical, preferably methyl, or a hydroxyl radical, A represents a d-Cs and preferably C3-C4 alkylene radical, and m and n are such that the weight-average molecular weight of the compound is between 5000 and 500 000 approximately. The compounds of this type are called "amodimethicone" in the CTFA dictionary.
According to a second possibility, R, R' and R", which may be identical or different, represent a C1-C4 alkoxy or hydroxyl radical, at least one of the radicals R or R" is an alkoxy radical and A represents a C3 alkylene radical. The hydroxy/alkoxy molar ratio is preferably between 0.2/1 and 0.4/1 and advantageously equal to 0.3/1 . Moreover, m and n are such that the weight-average molecular weight of the compound is between 2000 and 106. More particularly, n is between 0 and 999 and m is between 1 and 1000, the sum of n and m being between 1 and 1000. In this category of compounds, mention may be made, inter alia, of the product Belsil® ADM 652 sold by Wacker.
According to a third possibility, R and R", which are different, represent a C1-C4 alkoxy or hydroxyl radical, at least one of the radicals R or R" is an alkoxy radical, R' represents a methyl radical and A represents a C3 alkylene radical. The hydroxy/alkoxy molar ratio is preferably between 1/0.8 and 1/1 .1 , and advantageously is equal to 1/0.95. Moreover, m and n are such that the weight- average molecular weight of the compound is between 2000 and 200 000. More particularly, n is between 0 and 999 and m is between 1 and 1000, the sum of n and m being between 1 and 1000.
More particularly, mention may be made of the product Fluid WR® 1300 sold by Wacker.
The amino silicones used in the composition in accordance with the invention preferably have general formula (III) below:
Figure imgf000006_0001
in which:
A denotes a C2-C8 and preferably C2-C6, better still C3, linear or branched alkylene radical;
Ri and R2 denote, independently of one another, a C1-C4 alkyl, preferably methyl, radical or a C1-C4 alkoxy, preferably methoxy, radical or a hydroxyl radical, m and n are numbers such that the weight-average molecular weight (Mw) is greater than or equal to 75 000.
Preferably, the radicals R1 are identical and denote a hydroxyl radical.
Preferably, the viscosity of the amino silicone according to the invention is greater than 25 000 mm2/s measured at 25°C. More preferentially, the viscosity of the amino silicone is between 30 000 and 200 000 mm2/s at 25°C and even more preferentially between 50 000 and 150 000 mm2/s, measured at 25°C, and even better still from 70 000 to 120 000 mm2/s. The viscosities of the silicones are, for example, measured according to standard "ASTM 445 Appendix C".
Preferably, the cationic charge of the amino silicone according to the invention is less than or equal to 0.5 meq./g, preferably ranging from 0.01 to 0.1 meq./g and better still from 0.03 to 0.06 meq./g. Preferably, the amino silicone according to the invention has a weight-average molecular weight (Mw) ranging from 75 000 to 1 000 000 and even more preferentially ranging from 100 000 to 200 000.
The weight-average molecular weights of the amino silicones according to the invention are measured by gel permeation chromatography (GPC) at ambient temperature, as polystyrene equivalents. The columns used are μ styragel columns. The eluent is THF and the flow rate is 1 ml/minute. 200 μΙ of a solution containing 0.5% by weight of silicone in THF are injected. Detection is performed by refractometry and UV-metry.
A particularly preferred amino silicone corresponding to formula (III) is, for example, Dow Corning 2-8299® Cationic Emulsion from the company Dow Corning. A product corresponding to the definition of formula (I) is in particular the polymer called "trimethylsilylamodimethicone" in the CTFA dictionary, corresponding to formula (IV) below:
(CH,),
Figure imgf000007_0001
NH.
(IV)
in which n and m have the meanings given above in accordance with formula (II). Such compounds are described, for example, in EP 95238; a compound of formula (III) is, for example, sold under the name Q2-8220 by the company OSI.
Other amino silicones according to the invention are quaternized amino silicones, and in particular:
(a) the compounds corresponding to formula (V) below:
Figure imgf000008_0001
in which,
R3 represents a d-ds alkyl radical, for example methyl;
R4 represents a divalent hydrocarbon-based radical, in particular a d-ds alkylene radical;
Q" is an anion, in particular chloride;
r represents a mean statistical value from 2 to 20 and in particular from 2 to 8; s represents a mean statistical value from 20 to 200 and in particular from 20 to
50.
Such compounds are described more particularly in Patent US 4185087.
A compound falling within this class is the product sold by the company Union
Carbide under the name Ucar Silicone ALE 56;
(b) the quaternary ammonium silicones of formula (VI):
R„ -
Figure imgf000008_0002
in which:
R7, which may be identical or different, represent a monovalent hydrocarbon- based radical containing from 1 to 8 carbon atoms, and in particular a d-d alkyl radical, for example methyl;
R6 represents a divalent hydrocarbon-based radical, especially a d-ds alkylene radical or a divalent d-ds, and for example d-d, alkylenoxy radical linked to the Si via an SiC bond;
R8, which may be identical or different, represent a hydrogen atom, a monovalent hydrocarbon-based radical containing from 1 to 18 carbon atoms, and in particular a d-C-18 alkyl radical, a d-ds alkenyl radical or a radical -R6-NHCOR7;
X- is an anion such as a halide ion, especially chloride, or an organic acid salt (acetate, etc.);
r represents a mean statistical value from 2 to 200 and in particular from 5 to 100. These silicones are, for example, described in Application EP-A-0530974;
(c) the amino silicones of formula (VII):
Figure imgf000009_0001
NH.
(VII)
in which:
- R-i , R2, R3 and R4, which may be identical or different, denote a Ci-C4 alkyl radical or a phenyl group,
- R5 denotes a Ci-C4 alkyl radical or a hydroxyl group,
- n is an integer ranging from 1 to 5,
- m is an integer ranging from 1 to 5,
and in which x is selected such that the amine number is between 0.01 and 1 meq/g.
Preferably, the amino silicones of the invention are non-quaternized, i.e. they do not comprise a nitrogen atom with a permanent charge.
The silicones which are particularly preferred in accordance with the invention are polysiloxanes comprising amino groups, such as amodimethicones or trimethyl- silylamodimethicones, and in particular the compounds of formulae (II), (III) and (IV).
When the amino silicones of the invention are used, a particularly advantageous embodiment is their joint use with cationic and/or nonionic surfactants.
By way of example, it is possible to use the product sold under the name Cationic
Emulsion DC 929 by the company Dow Corning, which comprises, besides amodimethicone, a cationic surfactant comprising a mixture of products corresponding to the formula:
Figure imgf000009_0002
C H3
in which R5 denotes C-K-C22 alkenyl and/or alkyl radicals derived from tallow fatty acids, and known under the CTFA name tallowtrimonium chloride, in combination with a nonionic surfactant of formula: C9Hi 9-C6H4-(OC2H4)io-OH, known under the CTFA name Nonoxynol 10.
Use may also be made, for example, of the product sold under the name Cationic Emulsion DC 939 by the company Dow Corning, which comprises, besides amodimethicone, a cationic surfactant which is trimethylcetylammonium chloride and a nonionic surfactant of formula: Ci3H27-(OC2H4)i2-OH, known under the CTFA name Trideceth-12. When these amino silicones are used, one particularly advantageous embodiment consists in using them in the form of an oil-in-water emulsion.
The oil-in-water emulsion may comprise one or more surfactants. The surfactants may be of any nature but are preferably cationic and/or nonionic.
The silicone particles in the emulsion have a volume-average diameter [D4.3] generally ranging from 10 nm to 1000 nanometres, preferably from 50 nm to 800 nanometres, more particularly from 100 nm to 600 nanometres and even more particularly from 200 nm to 500 nanometres. These particle sizes may be determined especially using a laser granulometer, for example the Malvern Mastersizer 2000 granulometer.
According to the invention, all the silicones can also be used in the form of emulsions or of microemulsions.
According to the invention, the amino silicone(s) of formula (I) can represent from
0.001 % to 20% by weight, preferably from 0.01 % to 10% by weight and more particularly from 0.1 to 3% by weight, better still from 0.5 to 3% by weight, relative to the total weight of the final composition.
The liquid fatty esters (ii) that can be used in the present invention are preferably monomeric. They are preferably nonionic and non-silicone.
According to the invention, the term "liquid fatty esters" is intended to mean an ester which is liquid at ambient temperature (25°C) and at atmospheric pressure (1 atm) and which results from a carboxylic acid and an alcohol, at least one of these two constituents containing at least 7 carbon atoms.
The alcohol which makes it possible to form the ester function is a monoalcohol,
1. e. it comprises a single hydroxyl function.
The acyclic liquid fatty esters of a monoalcohol according to the invention are in particular chosen from:
1 ) esters of a C3-C30 aliphatic carboxylic acid and of a C1-C30 aliphatic monoalcohol, at least one of the acid or of the alcohol being branched or unsaturated (having at least one carbon-carbon double bond).
Preferably, the esters according to the invention are water-insoluble liquid esters. The water-insoluble liquid carboxylic acid esters are insoluble in water at a concentration greater than or equal to 0.1 % by weight in water at 25°C, i.e. they do not form, under these conditions, a macroscopically isotropic transparent solution. The total carbon number of the esters of the invention is generally greater than or equal to 10 and preferably less than 50 and more particularly less than 30.
The liquid esters of a C3-C30 carboxylic acid and of a C1-C30 monoalcohol, at least one of the acid or of the alcohol being branched or unsaturated, are in particular chosen from esters of a C6-C24 carboxylic acid and of a C3-C20 alcohol.
The esters according to the invention are in particular chosen from:
- esters of a linear carboxylic acid containing from 12 to 26 carbon atoms and of a branched alcohol containing from 3 to 12 carbon atoms,
- esters of a linear carboxylic acid containing from 2 to 12 carbon atoms and of a branched alcohol containing from 8 to 26 carbon atoms,
- esters of a branched carboxylic acid containing from 8 to 26 carbon atoms, preferably 8 to 12, and of a branched alcohol containing from 8 to 26 carbon atoms, preferably 8 to 12.
Mention may be made of octyldodecyl behenate; isocetyl behenate; isocetyl lactate; isostearyl lactate; linoleyl lactate; oleyl lactate; isostearyl octanoate; isocetyl octanoate; decyl oleate; isocetyl isostearate; isocetyl laurate; isocetyl stearate; isodecyl octanoate; isodecyl oleate; isononyl isononanoate; isostearyl palmitate; myristyl isostearate; octyl isononanoate; 2-ethylhexyl isononate; octyl isostearate; octyldodecyl erucate; isopropyl palmitates, 2-ethylhexyl palmitate, 2- octyldecyl palmitate, branched alkyl myristates such as isopropyl myristate, t-butyl myristate or 2-octyldodecyl myristate, hexyl isostearate, butyl isostearate, isobutyl stearate; 2-hexyldecyl laurate.
Use may also be made of esters of C4-C22 dicarboxylic or tricarboxylic acids and of C1-C22 monoalcohols.
Mention may in particular be made of diisopropyl sebacate; diisopropyl adipate; diisostearyl adipate; octyldodecyl stearoyl stearate; triisopropyl citrate; triisostearyl citrate; trioctyldodecyl citrate.
Use may also be made of liquid esters of a branched carboxylic acid containing from 4 to 6 carbon atoms and of a monoalcohol containing from 8 to 26 carbon atoms.
In this variant, the particular branched liquid esters preferably have the following formula: R1 COOR2 (VIII) in which:
R1 denotes a branched, optionally monohydroxylated or polyhydroxylated, hydrocarbon-based radical containing from 3 to 5 carbon atoms,
R2 denotes a linear or branched hydrocarbon-based radical containing from 12 to 26 carbon atoms, preferably containing from 16 to 22 carbon atoms. R1 preferably denotes a branched alkyl radical containing from 3 to 5 carbon atoms, and more particularly a tert-butyl radical.
R2 preferably denotes a saturated or unsaturated alkyl radical containing 12 to 26 carbon atoms, which is more particularly branched and even more particularly chosen from tridecyl, isocetyl, isostearyl, octyldodecyl and isoarachidyl radicals.
The branched liquid esters that are particularly preferred in this variant are isostearyl neopentanoate, tridecyl neopentanoate, isocetyl neopentanoate and isoarachidyl neopentanoate.
Preferably, the acid and the alcohol of the ester are saturated.
Among all the esters mentioned above, use is preferably made of isopropyl palmitate, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, branched alkyl myristates such as isopropyl myristate, t-butyl myristate or 2-octyldodecyl myristate, hexyl isostearate, butyl isostearate, isobutyl stearate; 2-hexyldecyl laurate, isostearyl neopentanoate, tridecyl neopentanoate and isononyl isononanoate, and more particularly isopropyl palmitate, isopropyl myristate and isostearyl neopentanoate. Isopropyl myristate is quite particularly preferred.
The liquid fatty ester(s) of the invention can represent from 0.01 % to 50% by weight, preferably from 0.1 % to 25% by weight, and even more preferentially from 0.2% to 15% by weight, of the total weight of the composition. For the purpose of the invention, the term "non-amino polydimethylsiloxanes" is intended to mean compounds different from the amino silicones of formula (I), and the repeating (R)(R')Si-0 groups of which are such that, when R and R' denote an alkyl group, then R and R' denote a methyl group.
The non-volatile, non-amino polydimethylsiloxanes that can be used in accordance with the invention preferably have a kinematic viscosity at 25°C greater than 350 cSt (mm2/s), even more preferentially a viscosity greater than 1000 cSt, and even more particularly greater than 10 000 cSt, better still greater than 50 000 cSt and preferably less than 10 000 000 cSt, better still less than 1 000 000 cSt, even better still less than 500 000 cSt.
The non-volatile, non-amino polydimethylsiloxanes that can be used in accordance with the invention are in particular polydimethylsiloxanes which are insoluble in the composition and can be in the form of oils, waxes, resins or gums. Mention may in particular be made of polydimethylsiloxanes with trimethylsilyl end groups having a viscosity of 10 x 10"6 to 2.5 m2/s at 25°C and preferably 10 x 10"5 to 1 m2/s. The viscosity of the silicones is measured, for example, at 25°C according to standard ASTM 445 Appendix C. Among these compounds, mention may be made, in a nonlimiting manner, of the following commercial products:
- the Silbione oils of the 70 047 series or the Mirasil oils sold by Bluestar, such as, for example, the oil 70 047 V 500 000;
- the oils of the 200 series from the company Dow Corning, such as, more particularly, DC200 with a viscosity of 60 000 cSt;
- the Viscasil oils from General Electric and certain oils of the SF series (SF 96, SF 18) from General Electric.
Mention may also be made of polydimethylsiloxanes with dimethylsilanol end groups (dimethiconol according to the CTFA name), such as the oils of the 48 series from the company Rhodia Chimie. The polydimethylsiloxane gums are in particular polydimethylsiloxanes having high number-average molar masses of between 200 000 and 1 000 000, used alone or as a mixture in a solvent. This solvent may be chosen from volatile silicones, polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffins, polyisobutylenes, methylene chloride, pentane, dodecane, tridecanes, or mixtures thereof.
Products that can be used more particularly are mixtures such as:
- mixtures formed from a gum of end-chain-hydroxylated polydimethylsiloxane (called dimethiconol according to the nomenclature of the CTFA dictionary) and a cyclic polydimethylsiloxane (called cyclomethicone according to the nomenclature of the CTFA dictionary), such as the product Q2 1401 sold by the company Dow Corning;
- mixtures formed from a polydimethylsiloxane gum with a cyclic silicone, such as the product SF 1214 Silicone Fluid from the company General Electric, this product is a gum SF 30 corresponding to a dimethicone, having a number-average molecular weight of 500 000, solubilized in the SF 1202 Silicone Fluid oil corresponding to decamethylcyclopentasiloxane;
- mixtures of two PDMSs (polydimethylsiloxanes) with different viscosities, and more particularly of a PDMS gum and of a PDMS oil, such as the product SF 1236 from the company General Electric. The product SF 1236 is a mixture of a gum SE 30 defined above with a viscosity of 20 m2/s and of an oil SF 96 with a viscosity of 5x10"6 m2/s. This product preferably comprises 15% of gum SE 30 and 85% of an oil SF 96. According to the invention, all the polydimethylsiloxanes can be used as they are or in the form of solutions, emulsions, nanoemulsions or microemulsions. The polydimethylsiloxanes that are particularly preferred in accordance with the invention are the polydimethylsiloxanes with trimethylsilyl end groups, such as the oils having a viscosity between 0.2 and 2.5 m2/s at 25°C, such as the oils of the DC200 series from Dow Corning, in particular the oil with a viscosity of 60 000 cSt or with a viscosity of 300 000 cSt, or the silicone sold under the name Belsil DM 300 000 by Wacker, and the polyalkylsiloxanes with dimethylsilanol end groups, such as dimethiconols.
According to the invention, the non-volatile, non-amino polydimethylsiloxane(s) can represent from 0.01 % to 25% by weight, preferably from 0.1 % to 15% by weight, and even more preferentially from 1 % to 10% by weight, of the total weight of the final composition.
According to one particular embodiment, the compositions according to the invention also comprise one or more agents that are beneficial to keratin materials, in particular the hair, such as in particular liquid fatty esters different from the fatty esters (ii), solid fatty esters of C1-C30 carboxylic acids and of monohydroxylated or polyhydroxylated C1-C30 alcohols, non-silicone cationic polymers, vegetable, animal, mineral or synthetic oils, waxes, ceramides or pseudoceramides, and mixtures thereof.
The compositions of the invention can thus comprise one or more non-silicone cationic or amphoteric polymers in particular chosen from all those already known per se, in particular those described in Patent Application EP-A-0 337 354 and in the French Patent Applications FR-A-2 270 846, 2 383 660, 2 598 61 1 , 2 470 596 and 2 519 863.
The cationic polymers used generally have a molecular weight of between 500 and 5 x 106 approximately, and preferably between 103 and 3 x 106 approximately. Among the cationic polymers, mention may be made of quaternized proteins (or protein hydrolysates) and polymers of the polyamine, polyaminoamide and polyquaternary ammonium type. These are known products.
The quaternized proteins or protein hydrolysates are in particular chemically modified polypeptides bearing quaternary ammonium groups at the end of the chain or grafted onto said chain. Their molecular weight can range, for example, from 1500 to 10 000, and in particular from 2000 to 5000 approximately. Among these compounds, mention may be made especially of:
- hydrolysates of collagen bearing triethylammonium groups, such as the products called "triethonium hydrolyzed collagen ethosulfate" in the CTFA dictionary;
hydrolysates of collagen bearing trimethylammonium chloride and trimethylstearylammonium chloride groups, called "steartrimonium hydrolyzed collagen" in the CTFA dictionary; - hydro lysates of proteins bearing, on the polypeptide chain, quaternary ammonium groups comprising at least one alkyl radical containing from 1 to 18 carbon atoms.
Among these protein hydrolysates, mention may be made, inter alia, of Croquat L, Croquat M, Croquat S and Crotein Q, sold by the company Croda.
Other quaternized proteins or hydrolysates are, for example, those sold by the company Inolex, under the name Lexein QX 3000.
Mention may also be made of quaternized vegetable proteins, such as wheat, maize or soya proteins; as quaternized wheat proteins, mention may be made of those called "cocodimonium hydrolysed wheat protein", "lauridimonium hydrolysed wheat protein" or else "steardimonium hydrolysed wheat protein" in the CTFA dictionary.
The polymers of polyamine, polyamidoamide and polyquaternary ammonium type, that can be used in accordance with the present invention, and that can in particular be mentioned, are those described in French Patents No. 2 505 348 or 2 542 997. Among these polymers, mention may be made of:
(1 ) homopolymers or copolymers derived from acrylic or methacrylic esters or amides and comprising at least one of the units of the following formulae:
Figure imgf000015_0001
(X)
R5 Rc
— CH2- C - CH2 - C—
O = O =
NH NH
I X
A
N Rc N R.
\
FL FL FL
(XI) (XII) in which: R3 and R4, which may be identical or different, represent hydrogen or an alkyl group containing from 1 to 6 carbon atoms, and preferably methyl or ethyl;
R5, which may be identical or different, denote a hydrogen atom or a radical CH3; A, which may be identical or different, represent a linear or branched alkyl group containing from 1 to 6 carbon atoms, preferably 2 or 3 carbon atoms, or a hydroxyalkyl group containing from 1 to 4 carbon atoms;
R6, R7 and R8, which may be identical or different, represent an alkyl group containing from 1 to 18 carbon atoms or a benzyl radical and preferably an alkyl group containing from 1 to 6 carbon atoms;
X denotes an inorganic or organic anion, such as a methosulphate anion or a halide such as chloride or bromide.
The copolymers of the family (1 ) may also contain one or more units deriving from comonomers which may be chosen from the family of acrylamides, methacrylamides, diacetone acrylamides, acrylamides and methacrylamides substituted on the nitrogen by lower alkyls (Ci-C4), acrylic acids or methacrylic acids or esters thereof, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, and vinyl esters. Thus, among these copolymers of the family (1 ), mention may be made of:
- copolymers of acrylamide and of dimethylaminoethyl methacrylate quaternized with dimethyl sulphate or with a dimethyl halide, such as the product sold under the name Hercofloc by the company Hercules,
- the copolymers of acrylamide and of methacryloyloxyethyltrimethylammonium chloride described, for example, in patent application EP-A-080 976 and sold under the name Bina Quat P 100 by the company Ciba Geigy,
- the copolymer of acrylamide and of methacryloyloxyethyltrimethylammonium methosulfate sold under the name Reten by the company Hercules,
- quaternized or non-quaternized vinylpyrrolidone/dialkylaminoalkyl acrylate or methacrylate copolymers, such as the products sold under the name Gafquat by the company ISP, such as, for example, Gafquat 734 or Gafquat 755, or alternatively the products known as Copolymer 845, 958 and 937. These polymers are described in detail in French Patents 2 077 143 and 2 393 573,
- dimethylaminoethyl methacrylate/vinylcaprolactam/vinylpyrrolidone terpolymers, such as the product sold under the name Gaffix VC 713 by the company ISP,
- vinylpyrrolidone/methacrylamidopropyldimethylamine copolymers sold in particular under the name Styleze CC 10 by ISP,
and vinylpyrrolidone/quaternized dimethylaminopropyl methacrylamide copolymers, such as the product sold under the name Gafquat HS 100 by the company ISP,
- crosslinked polymers of methacryloyloxy(Ci-C4)alkyl(Ci-C4)trialkylammonium salts, such as, for example, polymers obtained by homopolymerization of dimethylaminoethyl methacrylate quaternized with methyl chloride, or by copolymerization of acrylamide with dimethylaminoethyl methacrylate quaternized with methyl chloride, the homo or copolymerization being followed by crosslinking with a compound comprising an olefinic unsaturation, in particular methylenebis- acrylamide. Use may more particularly be made of a crosslinked acrylamide/methacryloyloxyethyltrimethylammonium chloride copolymer (20/80 by weight) in the form of a dispersion containing 50% by weight of said copolymer in mineral oil. This dispersion is sold under the name Salcare® SC 92 by the company BASF. Use may also be made of a crosslinked methacryloyloxyethyl- trimethylammonium chloride homopolymer containing approximately 50% by weight of the homopolymer in mineral oil or in a liquid ester. These dispersions are sold under the names Salcare® SC 95 and Salcare® SC 96 by the company BASF.
(2) Polymers formed from piperazinyl units and divalent alkylene or hydroxyalkylene radicals containing straight or branched chains, optionally interrupted with oxygen, sulphur or nitrogen atoms or with aromatic or heterocyclic rings, and also the oxidation and/or quaternization products of these polymers. Such polymers are especially described in French Patents 2 162 025 and 2 280 361 . (3) Water-soluble polyaminoamides prepared in particular by polycondensation of an acidic compound with a polyamine; these polyaminoamides can be crosslinked with an epihalohydrin, a diepoxide, a dianhydride, an unsaturated dianhydride, a bisunsaturated derivative, a bis-halohydrin, a bisazetidinium, a bis- haloacyldiamine, a bis-alkyl halide or alternatively with an oligomer resulting from the reaction of a difunctional compound which is reactive with a bis-halohydrin, a bis-azetidinium, a bis-haloacyldiamine, a bis-alkyl halide, an epihalohydrin, a diepoxide or a bis-unsaturated derivative; the crosslinking agent being used in proportions ranging from 0.025 to 0.35 mol per amine group of the polyaminoamide; these polyaminoamides can be alkylated or, if they comprise one or more tertiary amine functions, they can be quaternized. Such polymers are especially described in French Patents 2 252 840 and 2 368 508.
(4) Polyaminoamide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation with difunctional agents. Mention may be made, for example, of adipic acid/dialkylaminohydroxy- alkyldialkylenetriamine polymers in which the alkyl radical comprises from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl. Such polymers are especially described in French patent 1 583 363. Among these derivatives, mention may more particularly be made of the adipic acid/dimethylaminohydroxypropyl/diethylenetriamine polymers sold under the name Cartaretine F, F4 or F8 by the company Sandoz. (5) Polymers obtained by reaction of a polyalkylene polyamine containing two primary amine groups and at least one secondary amine group with a dicarboxylic acid chosen from diglycolic acid and saturated aliphatic dicarboxylic acids having from 3 to 8 carbon atoms. The molar ratio between the polyalkylene polyamine and the dicarboxylic acid is between 0.8: 1 and 1 .4: 1 ; the polyaminoamide resulting therefrom is reacted with epichlorohydrin in a molar ratio of epichlorohydrin relative to the secondary amine group of the polyaminoamide of between 0.5: 1 and 1 .8: 1 . Such polymers are described in particular in US patents 3 227 615 and 2 961 347.
Polymers of this type are in particular sold under the name Hercosett 57 by the company Hercules Inc. or else under the name PD 170 or Delsette 101 by the company Hercules in the case of the adipic acid/epoxypropyl/diethylenetriamine copolymer.
(6) Cyclopolymers of alkyldiallylamine or of dialkyldiallylammonium, such as homopolymers or copolymers comprising, as main constituent of the chain, units corresponding to formula (XIII) or (XIV):
(XIII)
Figure imgf000018_0001
R ° (XIV)
in which formulae k and t are equal to 0 or 1 , the sum k + t being equal to 1 ; R-|2 denotes a hydrogen atom or a methyl radical; R-io and R-n , independently of one another, denote an alkyl group containing from 1 to 6 carbon atoms, a hydroxyalkyl group in which the alkyl group preferably contains 1 to 5 carbon atoms, or a lower (C1-C4) amidoalkyl group, or R-io and R-n can denote, together with the nitrogen atom to which they are attached, heterocyclic groups, such as piperidinyl or morpholinyl; Y" is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulphate, bisulphite, sulphate or phosphate. These polymers are in particular described in French Patent 2 080 759 and its certificate of addition 2 190 406.
R-io and R-n , independently of one another, preferably denote an alkyl group containing from 1 to 4 carbon atoms.
Among the polymers defined above, mention may more particularly be made of the homopolymer of dimethyldiallylammonium chloride sold, for example under the name Merquat 100 by the company Nalco (and the low weight-average molecular weight homologues thereof) and the copolymers of diallyldimethylammonium chloride and of acrylamide sold, for example, under the name Merquat 550.
(7) The quaternary diammonium polymer containing repeating units corresponding to the formula:
R 13 R 15
Figure imgf000019_0001
in which formula (XV):
R-I 3, R-I 4, R-I 5 and R-|6, which may be identical or different, represent aliphatic, alicyclic or arylaliphatic radicals containing from 1 to 20 carbon atoms or lower hydroxyalkylaliphatic radicals, or else R-|3, Ru, R-|5 and R-|6, together or separately, constitute, with the nitrogen atoms to which they are attached, heterocycles optionally containing a second heteroatom other than nitrogen, or else R-I 3, Ru, R-| 5 and R-|6 represent a linear or branched d-C6 alkyl radical substituted with a nitrile, ester, acyl, amide, -CO-O-R17-D or -CO-NH-R-17-D group, where R-17 is an alkylene and D a quaternary ammonium group;
Ai and Bi represent polymethylene groups containing from 2 to 20 carbon atoms which may be linear or branched, and saturated or unsaturated, and which may contain, linked to or inserted in the main chain, one or more aromatic rings, or one or more oxygen or sulphur atoms or sulphoxide, sulphone, disulphide, amino, alkylamino, hydroxyl, quaternary ammonium, ureido, amide or ester groups, and X" denotes an anion derived from an inorganic or organic acid;
A-i , R-1 3 and R-15 can form, with the two nitrogen atoms to which they are attached, a piperazine ring; in addition, if Ai denotes a linear or branched, saturated or unsaturated alkylene or hydroxyalkylene radical, Bi can also denote a group (CH2)n-CO-D-OC-(CH2)p- in which:
n and p, which may be identical or different, are integers ranging from 2 to 20 approximately,
D denotes: a) a glycol residue of formula: -0-Z-0-, where Z denotes a linear or branched hydrocarbon-based radical or a group corresponding to one of the following formulae:
-(CH2-CH2-0)x -CH2-CH2- -[CH2-CH(CH3)-0]y-CH2-CH(CH3)- where x and y denote an integer from 1 to 4, representing a defined and unique degree of polymerization or any number from 1 to 4 representing an average degree of polymerization;
b) a bis-secondary diamine residue such as a piperazine derivative;
c) a bis-primary diamine residue of formula: -NH-Y-NH-, where Y denotes a linear or branched hydrocarbon-based radical, or alternatively the divalent radical -CH2-CH2-S-S-CH2-CH2-;
d) a ureylene group of formula: -NH-CO-NH-. Preferably, X" is an anion such as chloride or bromide.
These polymers have a number-average molecular weight generally between 1000 and 100 000. Polymers of this type are in particular described in French Patents 2 320 330, 2 270 846, 2 316 271 , 2 336 434 and 2 413 907 and US Patents 2 273 780, 2 375 853, 2 388 614, 2 454 547, 3 206 462, 2 261 002, 2 271 378, 3 874 870, 4 001 432, 3 929 990, 3 966 904, 4 005 193, 4 025 617, 4 025 627, 4 025 653, 4 026 945 and 4 027 020.
Use may be made more particularly of polymers that are formed from repeating units corresponding to the formula:
Figure imgf000020_0001
in which R-|8, R19, R20 and R21 , which may be identical or different, denote an alkyl or hydroxyalkyl radical containing from 1 to 4 carbon atoms approximately, r and s are integers ranging from 2 to 20 approximately, and X" is an anion derived from an inorganic or organic acid. A compound of formula (XVI) that is particularly preferred is that for which R-|8, R19, R20 and R21 represent a methyl radical and r = 3, s = 6 and X = CI, called hexadimethrine chloride in INCI nomenclature (CTFA).
(8) Polyquaternary ammonium polymers formed from units of formula (XVII): R
I I
— N+ - (CH2), - NH - CO - (CH2)U - CO - NH■ (CH2)V - N+ - A—
X- I I
R23 v R25
x- (xvii) in which formula:
R22, R23, R24 and R25, which may be identical or different, represent a hydrogen atom or a methyl, ethyl, propyl, β-hydroxyethyl, β-hydroxypropyl or -CH2CH2 (OCH2CH2)POH radical,
where p is equal to 0 or to an integer between 1 and 6, with the proviso that R22, R23, R24 and R25 do not simultaneously represent a hydrogen atom,
t and u, which may be identical or different, are integers between 1 and 6, v is equal to 0 or to an integer between 1 and 34,
X denotes an anion such as a halide,
A denotes a radical of a dihalide or preferably represents -CH2-CH2-O-CH2-
CH2-.
Such compounds are described especially in Patent Application EP-A-122 324. Among these, mention may be made, for example, of the products Mirapol® A 15, Mirapol® AD1 , Mirapol® AZ1 and Mirapol® 175, sold by the company Miranol.
(9) Quaternary polymers of vinylpyrrolidone and of vinylimidazole, for instance the products sold under the names Luviquat® FC 905, FC 550 and FC 370 by the company BASF.
(10) Cationic polysaccharides, especially cationic celluloses and galactomannan gums. Among the cationic polysaccharides, mention may be made more particularly of cellulose ether derivatives comprising quaternary ammonium groups, cationic cellulose copolymers or cellulose derivatives grafted with a water- soluble quaternary ammonium monomer and cationic galactomannan gums.
The cellulose ether derivatives comprising quaternary ammonium groups are described in French Patent 1 492 597. These polymers are also defined in the CTFA dictionary as quaternary ammoniums of hydroxyethylcellulose that have reacted with an epoxide substituted with a trimethylammonium group.
Cationic cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer are described especially in US patent 4 131 576, such as hydroxyalkyl celluloses, for instance hydroxymethyl-, hydroxyethyl- or hydroxypropylcelluloses grafted, in particular, with a methacryloylethyltrimethylammonium, methacrylamidopropyltrimethylammonium or dimethyldiallylammonium salt. The cationic galactomannan gums are described more particularly in US patents 3 589 578 and 4 031 307, in particular guar gums containing cationic trialkylammonium groups. Guar gums modified with a salt (e.g. chloride) of 2,3- epoxypropyltrimethylammonium are used, for example.
Other cationic polymers that may be used in the context of the invention are cationic proteins or cationic protein hydrolysates, polyalkyleneimines, in particular polyethyleneimines, polymers containing vinylpyridine or vinylpyridinium units, condensates of polyamines and of epichlorohydrin, quaternary polyureylenes and chitin derivatives.
Among all the cationic or amphoteric polymers that can be used in the context of the present invention, it is preferred to use quaternary cellulose ether derivatives, such as the products sold under the name JR 400 by the company Amerchol, cyclopolymers, in particular homopolymers of a diallyldimethylammonium salt and copolymers of a diallyldimethylammonium salt and of acrylamide, in particular the chlorides, sold under the names Merquat 550 and Merquat S by the company Nalco, cationic polysaccharides, and more particularly the guar gums modified with 2,3-epoxypropyltrimethylammonium chloride sold, for example, under the name Jaguar C13S by the company Rhodia Chimie, optionally crosslinked homopolymers and copolymers of a (meth)acryloyloxyethyltrimethylammonium salt, sold in particular by the company BASF as a 50% solution in mineral oil under the trade names Salcare SC92 (crosslinked copolymer of methacryloyloxyethyltrimethylammonium chloride and of acrylamide) and Salcare SC95 (crosslinked homopolymer of methacryloyloxyethyltrimethylammonium chloride), quaternary copolymers of vinylpyrrolidone and of a vinylimidazole salt, such as the products sold by BASF under the names Luviquat FC 370, Luviquat FC 550, Luviquat FC 905 and Luviquat HM-552. According to the invention, the additional beneficial agents can represent from 0.001 % to 20% by weight, preferably from 0.01 % to 10% by weight and more particularly from 0.05 to 5% by weight, relative to the total weight of the final composition. The compositions of the invention also advantageously contain one or more surfactants which are generally present in an amount between 0.01 % and 50% by weight approximately, preferably between 0.1 % and 40% and even more preferentially between 0.5% and 30%, relative to the total weight of the composition.
This surfactant or these surfactants can be chosen from anionic, amphoteric, nonionic and cationic surfactants, or mixtures thereof. The surfactants suitable for implementing the present invention are in particular the following:
(i) Anionic surfactant(s):
The term "anionic surfactant" is intended to mean a surfactant comprising, as ionic or ionizable groups, only anionic groups. These anionic groups are preferably chosen from the groups C02H, C02 ", S03H, S03 ", OS03H, OS03 ", 02P02H, 02P02H" and 02P022 ".
The anionic surfactant(s) that may be used in the compositions of the invention is (are) in particular chosen from alkyl sulphates, alkyl ether sulphates, alkylamidoether sulphates, alkylarylpolyether sulphates, monoglyceride sulphates, alkyl sulphonates, alkylamide sulphonates, alkylaryl sulphonates, alpha-olefin sulphonates, paraffin sulphonates, alkyl sulphosuccinates, alkyl ether sulphosuccinates, alkylamide sulphosuccinates, alkyl sulphoacetates, acyl sarcosinates, acyl glutamates, alkyl sulphosuccinamates, acyl isethionates and N- acyltaurates, salts of alkyl monoesters of polyglycoside-polycarboxylic acids, acyl lactylates, D-galactosiduronic acid salts, alky ether carboxylic acid salts, alkylaryl ether carboxylic acid salts, alkylamido ether carboxylic acid salts; or the non- salified forms of all these compounds, the alkyl and acyl groups of all these compounds containing from 6 to 24 carbon atoms and the aryl group denoting a phenyl group.
Some of these compounds may be oxyethylenated and then preferably comprise from 1 to 50 ethylene oxide units.
The salts of C6-C24 alkyl monoesters of polyglycoside-polycarboxylic acids can be chosen from C6-C24 alkyl polyglycoside citrates, C6-C24 alkyl polyglycoside- tartrates and C6-C24 alkyl polyglycoside-sulphosuccinates.
When the anionic surfactant(s) (i) is (are) in salt form, it (they) is (are) not in the form of zinc salts, and it (they) can be chosen from the alkali metal salts, such as the sodium or potassium salt and preferably the sodium salt, the ammonium salts, the amine salts and in particular amino alcohol salts, and the alkaline-earth metal salts, such as the magnesium salt.
By way of example of amino alcohol salts, mention may in particular be made of the mono-, di- and triethanolamine salts, the mono-, di- or triisopropanolamine salts, and the 2-amino-2-methyl-1 -propanol, 2-amino-2-methyl-1 ,3-propanediol and tris(hydroxymethyl)aminomethane salts.
Alkali metal or alkaline-earth metal salts, and in particular sodium or magnesium salts, are preferably used.
Use is preferably made of (C6-C24)alkyl sulphates and (C6-C24)alkyl ether sulphates, which are optionally oxyethylenated, comprising from 2 to 50 ethylene oxide units, and mixtures thereof, in particular in the form of alkali metal salts, alkaline-earth metal salts, ammonium salts or amino alcohol salts. More preferentially, the anionic surfactant(s) is (are) chosen from (Cio-C2o)alkyl ether sulphates, and in particular sodium lauryl ether sulphate comprising 2.2 mol of ethylene oxide.
When they are present, the amount of the anionic surfactant(s) preferably ranges from 0.1 to 50% by weight, even better still from 4 to 30% by weight, relative to the total weight of the composition.
(ii) Nonionic surfactant(s):
Nonionic surfactants are themselves also compounds that are well known per se (see especially in this regard the "Handbook of Surfactants" by M.R. Porter, published by Blackie & Son (Glasgow and London), 1991 , pp. 1 16-178). Thus, they can in particular be chosen from (nonlimiting list) alcohols, alpha-diols and alkylphenols, these compounds being polyethoxylated, polypropoxylated or polyglycerolated, and having at least one fatty chain containing for example 8 to 18 carbon atoms, it being possible for the number of ethylene oxide or propylene oxide groups to range in particular from 2 to 50 and for the number of glycerol groups to range in particular from 2 to 30. Mention may also be made of copolymers of ethylene oxide and of propylene oxide, condensates of ethylene oxide and of propylene oxide with fatty alcohols; polyethyoxylated fatty amides preferably having from 2 to 30 mol of ethylene oxide, polyglycerolated fatty amides comprising on average 1 to 5 glycerol groups and in particular 1.5 to 4; polyethoxylated fatty amines preferably having 2 to 30 mol of ethylene oxide; oxyethylenated fatty acid esters of sorbitan having from 2 to 30 mol of ethylene oxide; fatty acid esters of sucrose, fatty acid esters of polyethylene glycol, alkylpolyglycosides, N-alkylglucamine derivatives, and amine oxides, such as (C-io- Cu)alkylamine oxides or N-acylaminopropylmorpholine oxides. It will be noted that alkylpolyglycosides constitute nonionic surfactants that are particularly suitable within the context of the present invention.
(iii) Amphoteric surfactant(s):
The amphoteric or zwitterionic surfactant(s) that can be used in the present invention may in particular be derivatives of secondary or tertiary aliphatic amines, which are optionally quaternized, in which the aliphatic group is a linear or branched chain containing from 8 to 22 carbon atoms, said amine derivatives containing at least one anionic group such as, for example, a carboxylate, sulphonate, sulphate, phosphate or phosphonate group. Mention may in particular be made of (C8-C2o)alkylbetaines, sulphobetaines, (C8-C20 alkyl)amido(C3-C8 alkyl)betaines or (C8-C20 alkyl)amido(C6-C8 alkyl)sulphobetaines. Among the derivatives of optionally quaternized secondary or tertiary aliphatic amines that can be used, as defined above, mention may also be made of the compounds having the respective structures (XVIII) and (XIX) below:
Ra-CONHCH2CH2- N+(Rb)(Rc)(CH2COO-) (XVIII)
in which: Ra represents a C10-C30 alkyl or alkenyl group derived from an acid
Ra-COOH preferably present in hydrolysed coconut oil, or a heptyl, nonyl or undecyl group,
Rb represents a β-hydroxyethyl group, and
Rc represents a carboxymethyl group; and
Ra'-CONHCH2CH2-N(B)(B') (XIX)
in which:
B represents -CH2CH2OX,
B' represents -(CH2)Z-Y', with z = 1 or 2,
X represents the group -CH2-COOH, CH2-COOZ', -CH2CH2-COOH or -CH2CH2- COOZ', or a hydrogen atom,
Y' represents -COOH, -COOZ, or the group -CH2-CHOH-S03H or -CH2-CHOH-
Z' represents an ion derived from an alkali metal or alkaline-earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine,
Ra' represents a C10-C30 alkyl or alkenyl group of an acid Ra'-COOH preferably present in hydrolysed coconut oil or hydrolysed linseed oil, an alkyl group, in particular a C17 alkyl group, and its isoform, or an unsaturated C17 group.
These compounds are classified in the CTFA dictionary, 5th edition, 1993, under the names disodium cocoamphodiacetate, disodium lauroamphodiacetate, disodium caprylamphodiacetate, disodium capryloamphodiacetate, disodium cocoamphodipropionate, disodium lauroamphodipropionate, disodium caprylamphodipropionate, disodium capryloamphodipropionate, lauroampho- dipropionic acid and cocoamphodipropionic acid.
By way of example, mention may be made of the cocoamphodiacetate sold by the company Rhodia under the trade name Miranol® C2M Concentrate. Among the amphoteric or zwitterionic surfactants mentioned above, use is preferably made of (C8-C20 alkyl)betaines such as cocoylbetaine, (C8-C20 alkyl)amido(C2-C8 alkyl)betaines such as cocoylamidopropylbetaine, and mixtures thereof. More preferentially, the amphoteric or zwitterionic surfactant(s) is (are) chosen from cocoylamidopropylbetaine and cocoylbetaine.
When they are present, the amount of the amphoteric or zwitterionic surfactant(s) is preferably in the range from 0.01 % to 20% by weight, even better still from 0.5% to 10% by weight, relative to the total weight of the composition.
(iv) The cationic surfactants can be chosen from optionally polyoxyalkylenated primary, secondary or tertiary fatty amine salts, quaternary ammonium salts, and mixtures thereof.
By way of quaternary ammonium salts, mention may in particular be made, for example, of: - those corresponding to general formula (XX) below:
Figure imgf000026_0001
in which the groups R8 to R-n , which may be identical or different, each represent a linear or branched aliphatic group containing from 1 to 30 carbon atoms, or an aromatic group such as aryl or alkylaryl, at least one of the groups R8 to R-n containing from 8 to 30 carbon atoms, preferably from 12 to 24 carbon atoms. The aliphatic groups may comprise heteroatoms such as, in particular, oxygen, nitrogen, sulphur and halogens.
The aliphatic groups are chosen, for example, from C1-C30 alkyl, C1-C30 alkoxy, polyoxy(C2-C6)alkylene, C1-C30 alkylamide, (Ci2-C22)alkylamido(C2-C6)alkyl, (C12- C22)alkyl acetate, C1-C30 hydroxyalkyl groups, X" is an anion chosen from the group of halides, phosphates, acetates, lactates, (Ci-C4)alkyl sulfates, and (C-i- C4)alkyl- or (Ci-C4)alkylarylsulfonates.
Among the quaternary ammonium salts of formula (XX), preference is given to, on the one hand, tetraalkylammonium chlorides such as, for example, dialkyldimethyl- ammonium or alkyltrimethylammonium chlorides in which the alkyl group contains approximately from 12 to 22 carbon atoms, in particular behenyltrimethyl- ammonium, distearyldimethylammonium, cetyltrimethylammonium or benzyl- dimethylstearylammonium chlorides, or alternatively, on the other hand, distearoylethylhydroxyethylmethylammonium methosulphate, dipalmitoylethyl- hydroxyethylammonium methosulphate or distearoylethylhydroxyethylammonium methosulphate, or else finally, palmitylamidopropyltrimethylammonium chloride or the stearamidopropyldimethyl(myristyl acetate)ammonium chloride sold under the name Ceraphyl® 70 by the company Van Dyk;
- quaternary ammonium salts of imidazoline, for instance those of formula (XXI) below:
Figure imgf000026_0002
in which R-12 represents an alkenyl or alkyl group containing from 8 to 30 carbon atoms, for example tallow fatty acid derivatives, R-13 represents a hydrogen atom, a Ci-C4 alkyl group or an alkenyl or alkyl group containing from 8 to 30 carbon atoms, RH represents a Ci-C4 alkyl group, R-15 represents a hydrogen atom or a Ci-C4 alkyl group, and X" is an anion chosen from the group of halides, phosphates, acetates, lactates, (Ci-C4)alkyl sulphates, and (Ci-C4)alkyl- or (C-i- C4)alkylarylsulphonates. R-12 and Ri 3 preferably denote a mixture of alkyl or alkenyl groups containing from 12 to 21 carbon atoms, for example tallow fatty acid derivatives, Ru denotes a methyl group, and R-|5 denotes a hydrogen atom. Such a product is, for example, sold under the name Rewoquat® W 75 by the company Rewo;
- di- or triquaternary ammonium salts in particular of formula (XXII) below:
Figure imgf000027_0001
(XXII)
in which R-|6 denotes an alkyl group containing approximately from 16 to 30 carbon atoms, which is optionally hydroxylated and/or interrupted with one or more oxygen atoms; R-|7 is chosen from hydrogen, an alkyl group containing from 1 to 4 carbon atoms or a group -(CH2)3-N+(Ri6a)(Ri7a)(Ri 8a); Ri ea, Ri 7a, Ri ea, Ri e, Ri 9, R20 and R21 , which may be identical or different, are chosen from hydrogen and an alkyl group containing from 1 to 4 carbon atoms, and X" is an anion chosen from the group of halides, acetates, phosphates, nitrates, (Ci -C4)alkyl sulphates, and (Ci -C4)alkyl- or (Ci -C4)alkylarylsulphonates, in particular methyl sulphate and ethyl sulphate. Such compounds are, for example, Finquat CT-P, available from the company Finetex (Quaternium 89), and Finquat CT, available from the company Finetex (Quaternium 75);
- quaternary ammonium salts containing one or more ester functions, such as, for example, those of formula (XXIII) below:
Figure imgf000027_0002
(XXIII)
in which:
R22 is chosen from C1-C6 alkyl groups and C1 -C6 hydroxyalkyl or dihydroxyalkyl groups,
R23 is chosen from:
O I I
- the group R^g— C—
- radicals R27, which are linear or branched, saturated or unsaturated C1 -C22 hydrocarbon-based radicals,
- a hydrogen atom,
R25 is chosen from: - the group — C—
- radicals R29, which are linear or branched, saturated or unsaturated C1-C6 hydrocarbon-based radicals,
- a hydrogen atom,
R24, R26 and R28, which may be identical or different, are chosen from linear or branched, saturated or unsaturated C7-C21 hydrocarbon-based groups;
r, s and t, which may be identical or different, are integers ranging from 2 to 6, r1 and t1 , which may be identical or different, are equal to 0 or 1 ,
r2 + r1 = 2 r and t1 + t2 = 2 t,
y is an integer ranging from 1 to 10,
x and z, which may be identical or different, are integers ranging from 0 to 10, X" is a simple or complex, organic or inorganic anion,
with the proviso that the sum x + y + z equals from 1 to 15, that, when x is 0, then R23 denotes R27 and that, when z is 0, then R25 denotes R29.
The alkyl groups R22 may be linear or branched, and more particularly linear.
Preferably, R22 denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl group, and more particularly a methyl or ethyl group.
Advantageously, the sum x + y + z equals from 1 to 10.
When R23 is a hydrocarbon-based group R27, it may be long and contain from 12 to 20 carbon atoms, or short and contain from 1 to 3 carbon atoms.
When R25 is a hydrocarbon-based group R29, it preferably contains 1 to 3 carbon atoms.
Advantageously, R24, R26 and R28, which may be identical or different, are chosen from linear or branched, saturated or unsaturated C11-C21 hydrocarbon-based groups, and more particularly from linear or branched, saturated or unsaturated C11-C21 alkyl and alkenyl groups.
Preferably, x and z, which may be identical or different, equal 0 or 1.
Advantageously, y is equal to 1 .
Preferably, r, s and t, which may be identical or different, equal 2 or 3, and even more particularly are equal to 2.
The anion X" is preferably a halide, preferably chloride, bromide or iodide, a (C-i- C4)alkyl sulphate, or a (Ci-C4)alkyl- or (Ci-C4)akylarylsulphonate. However, it is possible to use methanesulphonate, phosphate, nitrate, tosylate, an anion derived from an organic acid, such as acetate or lactate, or any other anion that is compatible with the ammonium containing an ester function.
The anion X" is even more particularly chloride, methyl sulphate or ethyl sulphate. Use is more particularly made, in the composition according to the invention, of the ammonium salts of formula (XXIII) in which:
- R22 denotes a methyl or ethyl group,
- x and y are equal to 1 ,
- z is equal to 0 or 1 ,
- r, s and t are equal to 2, - R23 is chosen from:
• the group R26-C(0)-,
• methyl, ethyl or C14-C22 hydrocarbon-based groups
• a hydrogen atom,
- R25 is chosen from:
• the group R28-C(0)-,
• a hydrogen atom,
- R24, R26 and R28, which may be identical or different, are chosen from linear or branched, saturated or unsaturated C13-C17 hydrocarbon-based groups, and preferably from linear or branched, saturated or unsaturated C13-C17 alkyl and alkenyl groups
The hydrocarbon-based groups are advantageously linear.
Among the compounds of formula (XXIII), mention may be made, for example, of the salts, in particular diacyloxyethyldimethylammonium, diacyloxyethylhydroxy- ethylmethylammonium, monoacyloxyethyldihydroxyethylmethylammonium, triacyl- oxyethylmethylammonium and monoacyloxyethylhydroxyethyldimethylammonium chloride, diacyloxyethyldimethylammonium, diacyloxyethylhydroxyethylmethyl- ammonium, monoacyloxyethyldihydroxyethylmethylammonium, triacyloxyethyl- methylammonium and monoacyloxyethylhydroxyethyldimethylammonium methylsulphate, and mixtures thereof. The acyl groups preferably contain 14 to 18 carbon atoms and originate more particularly from a vegetable oil such as palm oil or sunflower oil. When the compound contains several acyl groups, these groups may be identical or different.
These products are obtained, for example, by direct esterification of triethanolamine, triisopropanolamine, an alkyldiethanolamine or an alkyldiisopropanolamine, which are optionally oxyalkylenated, with fatty acids or with fatty acid mixtures of plant or animal origin, or by transesterification of the methyl esters thereof. This esterification is followed by a quaternization by means of an alkylating agent such as an alkyl halide, preferably methyl or ethyl halide, a dialkyl sulfate, preferably methyl or ethyl sulfate, methyl methanesulfonate, methyl para-toluenesulfonate, glycol chlorohydrin or glycerol chlorohydrin.
Such compounds are, for example, sold under the names Dehyquart® by the company Henkel, Stepanquat® by the company Stepan, Noxamium® by the company Ceca or Rewoquat® WE 18 by the company Rewo-Witco.
The composition according to the invention may contain, for example, a mixture of quaternary ammonium salts of mono-, di- and triesters with a weight majority of diester salts.
The ammonium salts containing at least one ester function, described in Patents US-A-4 874 554 and US-A-4 137 180, can also be used.
Use may also be made of behenoylhydroxypropyltrimethylammonium chloride sold by the company KAO under the name Quartamin BTC 131 .
Preferably, the ammonium salts containing at least one ester function contain two ester functions. Among the cationic surfactants that may be present in the composition according to the invention, it is more particularly preferred to choose the cetyltrimethylammonium, behenyltrimethylammonium and dipalmitoylethylhydroxy- ethylmethylammonium salts, and mixtures thereof, and more particularly behenyl- trimethylammonium chloride, cetyltrimethylammonium chloride, dipalmitoylethyl- hydroxyethylammonium methosulphate, and mixtures thereof.
When they are present, the amount of the cationic surfactant(s) preferably ranges from 0.01 % to 20% by weight and even better still from 0.2% to 10% by weight, relative to the total weight of the composition.
In the compositions in accordance with the invention, use may be made of mixtures of surfactants and in particular mixtures of anionic surfactants, mixtures of anionic surfactants and amphoteric, cationic or nonionic surfactants, and mixtures of cationic surfactants with nonionic or amphoteric surfactants.
The composition of the invention may also contain one or more additives chosen from thickeners, anti-dandruff or anti-seborrheic agents, fragrances, hydroxy acids, electrolytes, preservatives, silicone or non-silicone sunscreens, vitamins, provitamins such as panthenol, anionic or nonionic polymers, proteins, protein hydrolysates, 18-methyleicosanoic acid, fluoro or perfluoro oils, fatty amines, fatty acids and derivatives thereof, fatty alcohols, and any other additive conventionally used in the cosmetics field which does not affect the properties of the compositions according to the invention. These additives are optionally present in the composition according to the invention in proportions that can range from 0.001 to 20% by weight, relative to the total weight of the composition. The precise amount of each additive is readily determined by those skilled in the art depending on its nature and its function. The compositions in accordance with the invention can also contain up to 5% of pearlescent agents or opacifiers well known in the prior art, such as, for example, sodium or magnesium palmitates, sodium or magnesium stearates and hydroxy- stearates, acylated fatty-chain derivatives, such as ethylene glycol monostearates or distearates or polyethylene glycol monostearates or distearates, fatty-chain ethers, such as, for example, distearyl ether or 1 -(hexadecyloxy)-2-octadecanol, fatty alcohols, in particular stearyl, cetyl and behenyl alcohols, and mixtures thereof.
The compositions can comprise a physiologically, and in particular cosmetically, acceptable medium.
The physiologically, and in particular cosmetically, acceptable medium can be made up solely of water, or of a mixture of water and at least one cosmetically acceptable solvent, such as a C1 -C4 lower alcohol, for instance ethanol, isopropanol, tert-butanol or n-butanol; polyols such as propylene glycol, or polyol ethers.
Preferably, the composition comprises from 50 to 95% by weight of water, relative to the total weight of the composition, and more particularly from 60 to 90% by weight.
The compositions according to the invention have a final pH which is generally between 3 and 10. Preferably, this pH is between 4 and 8 and more particularly from 4 to 6. The adjustment of the pH to the desired value can be carried out conventionally by adding a base (organic or inorganic) to the composition, for example aqueous ammonia or a primary, secondary or tertiary (poly)amine such as monoethanolamine, diethanolamine, triethanolamine, isopropanolamine or 1 ,3- propanediamine, or else by adding an inorganic or organic acid, preferably a carboxylic acid such as, for example, citric acid.
The compositions in accordance with the invention can be more particularly used for washing or treating keratin materials such as the hair, the skin, the eyelashes, the eyebrows, the nails, the lips or the scalp, and more particularly the hair. The compositions according to the invention are generally used as products in particular for washing, caring for, conditioning or retaining the form of the hairstyle or shaping keratin materials such as the hair.
The compositions of the invention can more particularly be in the form of a shampoo, a leave-in or rinse-out conditioner, permanent-waving, straightening, dyeing or bleaching compositions, or else in the form of compositions to be applied before or after dyeing, bleaching, permanent-waving or straightening, or else between the two steps of a permanent-waving or straightening operation.
In a first preferred variant, the compositions are washing and foaming compositions for the hair and/or the skin.
In particular, the compositions according to the invention are foaming detergent compositions such as shampoos, shower gels and bubble baths, or makeup- removing products. In this embodiment of the invention, the compositions comprise at least one or more detergent surfactants.
The surfactant(s) may then be without distinction chosen, alone or as a mixture, from anionic, amphoteric and nonionic surfactants, in particular as defined above. In the compositions in accordance with the invention in the form of detergent compositions, in particular shampoos, use is preferably made of at least one or more anionic surfactants or mixtures of at least one or more anionic surfactants and of at least one or more amphoteric surfactants or of at least one or more nonionic surfactants. A particularly preferred mixture is a mixture comprising at least one or more anionic surfactants and at least one or more amphoteric surfactants.
Use is preferably made of an anionic surfactant chosen from sodium, triethanolamine or ammonium (Ci2-Cu)alkyl sulphates, oxyethylenated sodium, triethanolamine or ammonium (Ci2-Cu)alkyl ether sulphates comprising 2.2 mol of ethylene oxide, sodium cocoyl isethionate and sodium alpha-(Cu-Ci6)olefin sulphonate, and mixtures thereof with:
- either an amphoteric surfactant such as the amine derivatives known as disodium cocoamphodipropionate or disodium cocoamphopropionate that are sold in particular by the company Rhodia Chimie under the trade name Miranol C2M CONC as an aqueous solution containing 38% of active material, or under the name Miranol C32;
- or an amphoteric surfactant of zwitterionic type, such as alkylbetaines, in particular the cocobetaine sold under the name Dehyton AB 30 as an aqueous solution containing 32% of AM, by the company Cognis, and the cocoamidopropyl- betaine sold in particular by Goldschmidt under the name Tegobetaine F50.
The minimum amount of surfactant is then that which is just sufficient to confer a satisfactory foaming and/or detergent power on the final composition.
Thus, according to the invention, the detergent surfactant can represent from 3% to 30% by weight, preferably from 6% to 25% by weight, and even more preferentially from 8% to 20% by weight, of the total weight of the final composition.
The foaming power of the compositions according to the invention, characterized by a foam height, is generally greater than 75 mm; preferably greater than 100 mm measured according to the modified Ross-Miles method (NF T 73-404/ISO696). The modifications of the method are the following:
The measurement is carried out at the temperature of 22°C with osmosed water. The concentration of the solution is 2 g/l. The height of the drop is 1 m. The amount of composition which drops is 200 ml. These 200 ml of composition fall into a graduating cylinder having a diameter of 50 mm and containing 50 ml of the test composition. The measurement is carried out 5 minutes after the flow of the composition is stopped.
In a second preferred variant, when the composition is in the form of a care composition such as an optionally rinse-out conditioner, it advantageously comprises one or more cationic surfactants, the concentration of said surfactants generally ranging from 0.1 to 10% by weight and preferably from 0.5 to 5% by weight, relative to the total weight of the composition. The compositions of the invention can also be in the form of permanent-waving, straightening, dyeing or bleaching compositions, or else in the form of compositions which are rinse-out, to be applied before or after dyeing, bleaching, permanent-waving or straightening or else between the two steps of a permanent- waving or straightening operation.
The compositions according to the invention can be in the form of aqueous or aqueous-alcoholic skincare and/or haircare lotions.
The cosmetic compositions according to the invention can be in the form of a gel, a milk, a cream, an emulsion, a thickened lotion or a mousse, and be used for the skin, the nails, the eyelashes, the lips and more particularly the hair.
The compositions can be packaged in various forms, in particular in vaporizers, pump-dispenser bottles or in aerosol or nonaerosol containers so as to apply the composition in vaporized form or in the form of a mousse. Such packaging forms are indicated, for example, when it is desired to obtain a spray, a lacquer or a mousse for treating the hair.
A subject of the invention is also a process for treating keratin materials such as the skin or the hair, characterized in that it consists in applying, to the keratin materials, a cosmetic composition as defined above, and then in optionally rinsing with water after an optional leave-in time.
In all that follows and in all the aforementioned, the percentages expressed are by weight.
The invention will now be more completely illustrated by means of the following examples which cannot be considered to limit the embodiments described.
In the examples, AM means active material.
EXAMPLE 1
The following leave-in care composition was prepared:
Figure imgf000033_0001
Figure imgf000034_0001
This composition is applied to the hair as a leave-in conditioner.
This composition according to the invention brings sheen and disentangling, but also smoothness and liveliness to the hair, in particular on sensitized hair.
EXAMPLE 2
The following leave-in care composition was prepared:
Figure imgf000034_0002
This composition is applied to hair as a leave-in conditioner.
This composition according to the invention brings sheen, smoothness and styling, but also liveliness and disentangling to the hair, in particular on sensitized hair. EXAMPLE 3
The following leave-in care composition was prepared:
Figure imgf000035_0002
This composition is applied to hair as a leave-in conditioner.
This composition according to the invention brings sheen, smoothness and styling, but also liveliness and disentangling to the hair, in particular on sensitized hair.
EXAMPLE 4
The following leave-in care composition was prepared:
Figure imgf000035_0001
Fragrance qs
Triethanolamine qs pH = 7.4
Water qs 100 g
EXAMPLE 5
The following two-phase leave-in care composition was prepared:
Figure imgf000036_0002
EXAMPLE 6 The following two-phase leave-in care composition was prepared:
Figure imgf000036_0001
Figure imgf000037_0001
EXAMPLE 7
The following leave-in spray care composition is prepared:
Figure imgf000037_0003
EXAMPLE 8
The following shampoo composition is prepared:
Figure imgf000037_0002
Figure imgf000038_0001
EXAMPLE 9
The following shampoo composition is prepared:
Figure imgf000038_0002
Figure imgf000039_0001
EXAMPLE 10
The following rinse-out conditioner composition is prepared:
Figure imgf000039_0002
Figure imgf000040_0001
EXAMPLE 1 1
The following rinse-out conditioner composition is prepared:
Figure imgf000040_0002
EXAMPLE 12
The following post-dye rinse-out care composition is prepared:
Figure imgf000041_0001
In all these compositions, it is possible to replace the isopropyl myristate with isostearyl neopentanoate, the Dow Corning 2-8299 amino silicone with the ADM LOG 1 silicone from Wacker, and the Belsil DM 300 000 polydimethylsiloxane from Wacker with the dimethicone/dimethiconol mixture sold by Dow Corning under the name 1403 Fluid.

Claims

1 . Cosmetic composition, characterized in that it comprises:
(i)- one or more non-volatile, non-amino polydimethylsiloxanes,
(ii) - one or more acyclic liquid fatty esters of a monoalcohol, and
(iii) - one or more amino silicones chosen from the compounds corresponding to formula (I) below: (Rl )a(T)3-a-Si[OSi(T)2]n-[OSi(T)b(R1)2-b]m-OSi(T)3-a-( 1)a in which:
T is a hydrogen atom, or a phenyl, hydroxyl, or d-Cs alkyl, or d-Cs alkoxy, radical,
a denotes the number 0 or an integer from 1 to 3,
b denotes 0 or 1 ,
m and n are numbers such that the sum (n + m) can range especially from 1 to 2000, it being possible for n to denote a number from 0 to 1999, and for m to denote a number from 1 to 2000;
R1 is a monovalent radical of formula -CqH2qL in which q is a number from 2 to 8, it being possible for one or more hydrogen atoms to be substituted with a hydroxyl group, and L is an optionally quaternized amino group chosen from the groups: -N(R2)-CH2-CH2-N(R2)2;
-N(R2)2;
-N+(R2)3 Q";
-N+(R2) (H)2 Q";
-N+(R2)2HQ";
-N(R2)-CH2-CH2-N+(R2)(H)2 Q",
in which R2 can denote a hydrogen atom, a phenyl, a benzyl, or a monovalent saturated hydrocarbon-based radical, for example a C1 -C20 alkyl radical, and Q" represents an anion such as, for example, fluoride, chloride, bromide or iodide.
2. Cosmetic composition according to Claim 1 , characterized in that the amino silicone corresponding to formula (I) is chosen from the compounds corresponding to the formula below:
Figure imgf000043_0001
in which R, R' and R", which may be identical or different, denote a C1-C4 alkyl radical, a Ci-C4 alkoxy radical or OH; A represents a linear or branched, C3-C8 alkylene radical; m and n are integers dependent on the molecular weight and the sum of which is between 1 and 2000.
3. Cosmetic composition according to Claim 2, characterized in that the silicone of formula (I) is the silicone corresponding to formula (III) below:
(CH3)3
Figure imgf000043_0002
in which n and m have the meanings indicated in formula (I).
4. Cosmetic composition according to any one of the preceding claims, characterized in that the amino silicone(s) represent(s) from 0.001 % to 20% by weight, preferably from 0.01 % to 10% by weight and more particularly from 0.1 to 3% by weight, better still from 0.5 to 3% by weight, relative to the total weight of the final composition.
5. Cosmetic composition according to any one of the preceding claims, characterized in that the amino silicone of formula (I) has a weight-average molecular weight (Mw) ranging from 75 000 to 1 000 000 and even more preferentially ranging from 100 000 to 200 000.
6. Cosmetic composition according to any one of the preceding claims, characterized in that the liquid fatty ester is chosen from:
- esters of a linear carboxylic acid containing from 12 to 26 carbon atoms and of a branched alcohol containing from 3 to 12 carbon atoms,
- esters of a linear carboxylic acid containing from 2 to 12 carbon atoms and of a branched alcohol containing from 8 to 26 carbon atoms,
- esters of a branched carboxylic acid containing from 8 to 26 carbon atoms, preferably 8 to 12, and of a branched alcohol containing from 8 to 26 carbon atoms, preferably 8 to 12, and
- liquid esters of a branched carboxylic acid containing from 4 to 6 carbon atoms and of a monoalcohol containing from 8 to 26 carbon atoms.
7. Cosmetic omposition according to any one of the preceding claims, characterized in that the ester is chosen from octyldodecyl behenate; isocetyl behenate; isocetyl lactate; isostearyl lactate; linoleyl lactate; oleyl lactate; isostearyl octanoate; isocetyl octanoate; decyl oleate; isocetyl isostearate; isocetyl laurate; isocetyl stearate; isodecyl octanoate; isodecyl oleate; isononyl isononanoate; isostearyl palmitate; myristyl isostearate; octyl isononanoate; 2- ethylhexyl isononate; octyl isostearate; octyldodecyl erucate; isopropyl palmitates, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, branched alkyl myristates such as isopropyl myristate, t-butyl myristate or 2-octyldectyl myristate, hexyl isostearate, butyl isostearate, isobutyl stearate; 2-hexyldecyl laurate, diisopropyl sebacate; diisopropyl adipate; diisostearyl adipate; octyldodecyl stearoyl stearate; pentaerythrityl tetraisononanoate; pentaerythrityl tetraisostearate; triisopropyl citrate; triisostearyl citrate; trioctyldodecyl citrate, isostearyl neopentanoate and tridecyl neopentanoate.
8. Cosmetic omposition according to any one of the preceding claims, characterized in that the liquid fatty ester (ii) is chosen from isopropyl palmitate, isopropyl myristate and isostearyl neopentanoate, and is preferably isopropyl myristate.
9. Cosmetic omposition according to any one of the preceding claims, characterized in that the liquid fatty ester(s) (ii) is (are) present at a concentration ranging from 0.01 % to 50% by weight, preferably from 0.1 % to 25% by weight and even more preferentially from 0.2% to 15% by weight, of the total weight of the composition.
10. Cosmectic composition according to any one of the preceding claims, characterized in that the non-volatile, non-amino polydimethylsiloxanes have a viscosity at 25°C greater than 350 cSt (mm2/s), even more preferentially a viscosity greater than l OOO cSt, and even more particularly greater than l O OOO cSt, better still greater than 50 000 cSt and preferably less than l O OOO OOO cSt, better still less than 1 000 000 cSt, even better still less than 500 000 cSt.
1 1 . Cosmetic composition according to any one of the preceding claims, characterized in that the non-volatile, non-amino polydimethylsiloxane(s) represent(s) from 0.01 % to 25% by weight, preferably from 0.1 % to 15% by weight, and even more preferentially from 1 % to 10% by weight, of the total weight of the final composition.
12. Cosmetic composition according to any one of the preceding claims, characterized in that it also comprises one or more additional agents that are beneficial to keratin materials, chosen from solid fatty esters of C1-C30 carboxylic acids and of monohydroxylated or polyhydroxylated C1-C30 alcohols, vegetable, animal, mineral or synthetic oils, waxes, ceramides, pseudoceramides and non- silicone cationic polymers, and mixtures thereof.
13. Composition according to Claim 12, characterized in that the additional beneficial agents represent from 0.001 % to 20% by weight, preferably from 0.01 % to 10% by weight and more particularly from 0.05 to 5% by weight, relative to the total weight of the final composition.
14. Cosmetic composition according to any one of the preceding claims, characterized in that it also comprises one or more surfactants chosen from anionic, nonionic, amphoteric and cationic surfactants, and mixtures thereof.
15. Cosmetic composition according to any one of the preceding claims, characterized in that it constitutes a rinse-out or leave-in conditioner composition, or a foaming detergent composition such as shampoo, shower gel, makeup- removing product and bubble bath.
16. Use of a cosmetic composition as defined in any one of Claims 1 to 15, for washing or for caring for keratin materials.
17. Process for treating keratin materials, such as the hair, characterized in that it consists in applying, to said materials, a cosmetic composition according to any one of Claims 1 to 15, and then in optionally rinsing with water after an optional leave-in time.
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