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WO2017054170A1 - Composition pour le traitement de fibres de kératine - Google Patents

Composition pour le traitement de fibres de kératine Download PDF

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Publication number
WO2017054170A1
WO2017054170A1 PCT/CN2015/091214 CN2015091214W WO2017054170A1 WO 2017054170 A1 WO2017054170 A1 WO 2017054170A1 CN 2015091214 W CN2015091214 W CN 2015091214W WO 2017054170 A1 WO2017054170 A1 WO 2017054170A1
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WIPO (PCT)
Prior art keywords
group
polymers
denotes
carbon atoms
radical
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PCT/CN2015/091214
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English (en)
Inventor
Jingya Dai
Wi Soon CHIA
Original Assignee
L'oreal
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Priority to CN201580083541.8A priority Critical patent/CN108135791A/zh
Priority to PCT/CN2015/091214 priority patent/WO2017054170A1/fr
Publication of WO2017054170A1 publication Critical patent/WO2017054170A1/fr

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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
    • A61K8/86—Polyethers
    • 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
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4993—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—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
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
    • 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
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5428—Polymers characterized by specific structures/properties characterized by the charge amphoteric or zwitterionic
    • 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
    • A61K2800/596—Mixtures of surface active compounds

Definitions

  • the present invention relates to a composition for treating keratin fibers, comprising one or more silicone oil (s) , one or more cationic and/or amphoteric polymer and a particular combination of surfactants comprising a cationic surfactant and a non-ionic surfactant.
  • the invention also relates to a cosmetic process for treating keratin fibres using this composition.
  • the invention further concerns the use of this composition in the cosmetic treatment of keratin fibres and in particular the hair.
  • Hair is generally damaged and embrittled by the action of external atmospheric agents such as light and bad weather, and also by mechanical or chemical treatments, such as brushing, combing, dyeing, bleaching, permanent-waving and/or relaxing.
  • conditioning agents intended mainly to repair or to limit the harmful or undesirable effects brought about by the various treatments or attacks to which hair fibres are more or less repeatedly subjected.
  • These conditioning agents can also be used for improving the cosmetic behaviour of natural hair, in particular giving it shine, a softer feel and tone, a good level of discipline.
  • compositions often comprise silicones, which are used as conditioning agents so as to give the hair a satisfactory level of care, especially in terms of shine, softness, smoothness and suppleness.
  • compositions as mentioned above often have the drawback of making the hair very lank and heavy, which leads to the phenomenon commonly known as the "build-up effect” , and which has the consequence of making the head of hair lank, greasy and/or sticky, which is unpleasant for consumers.
  • compositions may also have the drawback of giving to the hair an unnatural aspect.
  • compositions in particular hair conditioners, that do not have the drawbacks described above, i.e. which are capable of treating and positively conditioning the hair, especially sensitized hair, namely by affording it softness, smoothness and suppleness while at the same time leaving it more light and natural.
  • compositions containing silicone oils are sometimes difficult to apply to hair and to spread along the hair shafts.
  • compositions for treating keratin fibres which have the desired properties, by combining in these compositions at least one silicone oil and at least one cationic or amphoteric polymer with a particular combination of surfactants comprising a specific cationic surfactant and a specific non-ionic surfactant.
  • composition according to the invention has improved usage qualities and can be applied and spread easily along the hair shafts.
  • composition of the invention allows depositing selectively a suitable amount of silicones on hair, especially on sensitized hair, in order to maintain or improve the cosmetic properties conferred to it while at the same time leaving it more light and natural.
  • the hair is less lank, less heavy, neither sticky nor greasy, while the cosmetic properties are not impacted.
  • Fibres treated using this composition are soft, smooth to the touch, and detangle very easily.
  • the composition confers to the fibres a particularly remarkable level of suppleness just immediately after the application that lasts all day long.
  • the composition according to the invention also provides more volume, shape, density and body to the keratin fibres.
  • the fibers are better individualized, and lighter.
  • the composition is particularly effective for achieving a good hair styling (in particular for managing and disciplining the hair) and has excellent anti-frizz properties.
  • the conditioning properties conferred to the keratin fibres are long lasting.
  • composition according to the invention is stable over time.
  • stable over time means that the composition after two months of storage at 25 to 45°C, shows no change in appearance, colour, odour, or viscosity.
  • composition for treating keratin fibers comprising:
  • polymer (s) chosen from cationic polymers and amphoteric polymers
  • radicals R 1 to R 4 which may be identical or different, represent a linear or branched aliphatic radical comprising from 1 to 30 carbon atoms, or an aromatic radical such as aryl or alkylaryl, with at least one of the radicals R 1 to R 4 denoting a linear or branched alkyl radical comprising from 10 to 30 carbon atoms, and X - denotes an anion; and
  • non-ionic surfactant chosen from oxyethylenated esters of fatty acid and of sorbitan.
  • composition according to the invention is useful for treating keratin fibres, in particular human keratin fibres such as the hair.
  • the present invention also relates to a non-therapeutical process for treating the keratin fibres, comprising the application to the said fibres of the composition according to the invention.
  • the invention also relates to the use of the composition according to the invention as a hair conditioner, to be applied preferably after the application of a shampoo.
  • composition according to the present invention comprises one or more silicone oil (s) .
  • sicone is intended to denote, in accordance with what is generally accepted, any organosilicon polymer or oligomer of linear or cyclic, branched or crosslinked structure, of variable molecular weight, obtained by polymerization and/or polycondensation of suitably functionalized silanes, and consisting essentially of a repetition of main units in which the silicon atoms are linked together via oxygen atoms (siloxane bond -Si-O-Si-) , optionally substituted hydrocarbon-based radicals being directly linked via a carbon atom to the said silicon atoms.
  • hydrocarbon-based radicals that are the most common are alkyl radicals, especially C 1 -C 10 alkyl radicals, and in particular methyl, fluoroalkyl radicals, the alkyl part of which is C 1 -C 10 , and aryl radicals and in particular phenyl.
  • silicone oil it is meant a silicone that is liquid at room temperature (25°C) and at atmospheric pressure (760 mm Hg; i.e. 1.013 ⁇ 10 5 Pa) .
  • silicone oils which can be used in the composition according to the invention, can be in particular chosen from polyorganosiloxanes.
  • Organopolysiloxanes are defined in greater detail in Walter Noll’s Chemistry and Technology of Silicones (1968) , Academic Press.
  • the silicones may be volatile or non-volatile.
  • the silicones are more particularly chosen from: cyclic silicones comprising from 3 to 7 and preferably 4 to 5 silicon atoms; linear volatile silicones containing 2 to 9 silicon atoms, for example those described in the article published in Cosmetics and Toiletries, Vol. 91, Jan. 76, pp. 27-32, Todd &Byers Volatile Silicone Fluids for Cosmetics.
  • silicones are non-volatile, use is preferably made of polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, silicone gums and resins, and polyorganosiloxanes modified with organofunctional groups, and mixtures thereof.
  • silicones are more particularly chosen from polyalkylsiloxanes, among which mention may be made mainly of polydimethylsiloxanes containing trimethylsilyl end groups (Dimethicone according to the CTFA name) such as:
  • oils of the 200 series from the company Dow Corning such as, more particularly, DC200 with a viscosity of 60 000 cSt,
  • the polyalkylarylsiloxanes are particularly chosen from linear and/or branched polydimethylmethylphenylsiloxanes and polydimethyldiphenylsiloxanes.
  • the silicones used in the composition according to the present invention may further be chosen from organomodified silicones.
  • organomodified silicones that may be present in the composition according to the invention are silicones as defined above and comprising in their structure one or more organofunctional groups attached via a hydrocarbon-based group.
  • the silicones used in the composition according to the present invention may further be chosen from amino silicones.
  • amino silicone means any silicone comprising at least one primary, secondary or tertiary amine function or a quaternary ammonium group.
  • -T is a hydrogen atom or a phenyl, hydroxyl (-OH) or C 1 -C 8 alkyl group, and preferably methyl, or a C 1 -C 8 alkoxy, preferably methoxy,
  • -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 + 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 m to denote a number from 1 to 2000 and in particular from 1 to 10, and
  • -R 1 is a monovalent group of formula -C q H 2q L in which q is a number from 2 to 8 and L is an optionally quaternized amino group chosen from the following groups:
  • R 2 may denote a hydrogen atom, a phenyl, a benzyl or a saturated monovalent hydrocarbon-based group, for example a C 1 -C 20 alkyl group
  • Q - represents a halide ion, for instance fluoride, chloride, bromide or iodide.
  • amino silicones corresponding to the definition of formula (X) are chosen from the compounds corresponding to formula (XI) below:
  • R, R’ and R which may be identical or different, denote a C 1 -C 4 alkyl group, preferably CH 3 ; a C 1 -C 4 alkoxy group, preferably methoxy; or OH;
  • A represents a linear or branched, C 3 -C 8 and preferably C 3 -C 6 alkylene group;
  • m and n are integers dependent on the molecular weight and whose sum is between 1 and 2000.
  • R, R’ and R which may be identical or different, represent a C 1 -C 4 alkyl or hydroxyl group
  • A represents a C 3 alkylene group
  • m and n are such that the weight-average molecular mass of the compound is between 5000 and 500 000 approximately.
  • Compounds of this type are referred to in the CTFA dictionary as “amodimethicones” .
  • R, R’ a nd R” which may be identical or different, each represent a C 1 -C 4 alkoxy or hydroxyl group, at least one of the groups R or R” is an alkoxy group and A represents a C 3 alkylene group.
  • the hydroxy/alkoxy mole 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 mass 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.
  • ADM LOG 1 Another commercial product that may be used according to the invention is the product sold under the name ADM LOG 1 by Wacker, comprising, in microemulsion form, an amodimethicone in combination with Trideceth-5 and Trideceth-10.
  • R and R which are different, each represent a C 1 -C 4 alkoxy or hydroxyl group, at least one of the groups R or R” being an alkoxy group, R’ representing a methyl group and A representing a C 3 alkylene group.
  • the hydroxy/alkoxy mole ratio is preferably between 1/0.8 and 1/1.1 and advantageously equal to 1/0.95.
  • m and n are such that the weight-average molecular mass 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.
  • the molecular mass of these silicones is determined by gel permeation chromatography (ambient temperature, polystyrene standard; ⁇ styragem columns; eluent THF; flow rate 1 mm/minute; 200 ⁇ l of a solution containing 0.5%by weight of silicone in THF are injected, and detection is performed by refractometry and UV-metry) .
  • a product corresponding to the definition of formula (IX) is in particular the polymer known in the CTFA dictionary as Trimethylsilyl Amodimethicone, corresponding to formula (XII) below:
  • n and m have the meanings given above in accordance with formula (X) .
  • a compound of formula (XII) is sold, for example, under the name Q2-8220 by the company OSI.
  • -R 3 represents a C 1 -C 18 monovalent hydrocarbon-based group, and in particular a C 1 -C 18 alkyl or C 2 -C 18 alkenyl group, for example methyl,
  • -R 4 represents a divalent hydrocarbon-based group, especially a C 1 -C 18 alkylene group or a divalent C 1 -C 18 , and for example C 1 -C 8 , alkylenoxy group,
  • -Q - is a halide ion, in particular chloride
  • -r represents a mean statistical value from 2 to 20 and in particular from 2 to 8, and
  • -s represents a mean statistical value from 20 to 200 and in particular from 20 to 50.
  • a compound falling within this class is the product sold by the company Union Carbide under the name Ucar Silicone ALE 56.
  • R 7 which may be identical or different, represent a monovalent hydrocarbon-based group containing from 1 to 18 carbon atoms, and in particular a C 1 -C 18 alkyl group, a C 2 -C 18 alkenyl group or a ring comprising 5 or 6 carbon atoms, for example methyl,
  • -R 6 represents a divalent hydrocarbon-based group, especially a C 1 -C 18 alkylene group or a divalent C 1 -C 18 , and for example C 1 -C 8 , alkylenoxy group linked to the Si via an SiC bond,
  • -R 8 which may be identical or different, represent a hydrogen atom, a monovalent hydrocarbon-based group containing from 1 to 18 carbon atoms, and in particular a C 1 -C 18 alkyl group, a C 2 -C 18 alkenyl group or a group -R 6 -NHCOR 7 ;
  • -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 1 , R 2 , R 3 and R 4 which may be identical or different, denote a C 1 -C 4 alkyl group or a phenyl group,
  • -R 5 denotes a C 1 -C 4 alkyl group or a hydroxyl group
  • -n is an integer ranging from 1 to 5
  • -m is an integer ranging from 1 to 5
  • -x is chosen such that the amine number is between 0.01 and 1 meq/g.
  • one particularly advantageous embodiment involves their combined use with cationic and/or nonionic surfactants.
  • a cationic surfactant namely trimethylcetylammonium chloride and a nonionic surfactant of formula C 13 H 27 - (OC 2 H 4 ) 12 -OH, known under the CTFA name Trideceth-12.
  • Another commercial product that may be used according to the invention is the product sold under the name Dow Corning Q2 7224 by the company Dow Corning, comprising, in combination, trimethylsilyl amodimethicone of formula (XI) described above, a non-ionic surfactant of formula C 8 H 17 -C 6 H 4 - (OCH 2 CH 2 ) 40 -OH, known under the CTFA name Octoxynol-40, a second non-ionic surfactant of formula C 12 H 25 - (OCH 2 -CH 2 ) 6 -OH, known under the CTFA name Isolaureth-6, and propylene glycol.
  • Dow Corning Q2 7224 by the company Dow Corning, comprising, in combination, trimethylsilyl amodimethicone of formula (XI) described above, a non-ionic surfactant of formula C 8 H 17 -C 6 H 4 - (OCH 2 CH 2 ) 40 -OH, known under the CTFA name Octoxynol-40,
  • the silicones of the invention may also be silicones grafted with anionic groups, such as the compounds VS 80 or VS 70 sold by the company 3M.
  • amino silicones that can be used in the present invention are the products sold under the names DC 8194, DC 8299, DC 1689, DC 5-7113, DC 8500, DC 8566, DC8170 and DC 8401 by the company Dow Corning.
  • the silicone oils used in the composition of the present inventions are chosen from polyalkylsiloxanes, amino-silicones and mixtures thereof, and more preferentially from polydimethylsiloxanes, amodimethicones and mixtures thereof.
  • the amount of silicone oil advantageously ranges from 0.01 to 15%by weight, and more preferentially from 0.1 to 10%by weight, relative to the total weight of the composition.
  • composition of the invention comprises one or more polymer (s) , chosen from cationic polymers and amphoteric polymers.
  • cationic polymer is intended to mean any polymer comprising cationic groups and/or groups that can be ionized to cationic groups.
  • the cationic polymer is hydrophilic or amphiphilic.
  • the preferred cationic polymers are chosen from those that contain units comprising primary, secondary, tertiary and/or quaternary amine groups that may either form part of the main polymer chain or may be borne by a side substituent directly connected thereto.
  • cationic polymers mention may be made more particularly of:
  • -R 3 which may be identical or different, denote a hydrogen atom or a CH 3 group
  • -A which may be identical or different, represent a linear or branched divalent alkyl group of 1 to 6 carbon atoms, preferably 2 or 3 carbon atoms, or a hydroxyalkyl group of 1 to 4 carbon atoms;
  • R 4 , R 5 and R 6 which may be identical or different, represent an alkyl group containing from 1 to 18 carbon atoms or a benzyl group, and preferably an alkyl group containing from 1 to 6 carbon atoms;
  • R 1 and R 2 which may be identical or different, represent a hydrogen atom or an alkyl group containing from 1 to 6 carbon atoms, and preferably methyl or ethyl;
  • -X denotes an anion derived from an inorganic or organic acid, such as a methosulfate anion or a halide such as chloride or bromide.
  • the copolymers of family (1) may also contain one or more units derived from comonomers which may be chosen from the family of acrylamides, methacrylamides, diacetone acrylamides, acrylamides and methacrylamides substituted on the nitrogen with C 1- C 4 alkyls, acrylic or methacrylic acids or esters thereof, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, and vinyl esters.
  • Cationic polysaccharides in particular cationic celluloses and cationic 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 in particular described in FR patent 1 492 597, and mention may be made of the polymers sold under the name Ucare Polymer JR (JR 400 LT, JR 125 and JR 30M) or LR (LR 400 or LR 30M) by the company Amerchol. 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.
  • Water-soluble polyaminoamides prepared in particular by polycondensation of an acidic compound with a polyamine; these polyaminoamides can be crosslinked by an epihalohydrin, a diepoxide, a dianhydride, an unsaturated dianhydride, a bisunsaturated derivative, a bishalohydrin, a bisazetidinium, a bishaloacyldiamine or an alkyl bishalide or alternatively by an oligomer resulting from the reaction of a bifunctional compound reactive with respect to a bishalohydrin, a bisazetidinium, a bishaloacyldiamine, an alkyl bishalide, an epihalohydrin, a diepoxide or a bisunsaturated 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
  • Polyaminoamide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation with difunctional agents (6) Polymers obtained by reaction of a polyalkylenepolyamine comprising 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 of polyalkylenepolyamine to dicarboxylic acid preferably being of between 0.8:1 and 1.4:1; the polyaminoamide resulting therefrom being reacted with epichlorohydrin in a molar ratio of epichlorohydrin in relation to the secondary amine group of the polyaminoamide preferably of between 0.5:1 and 1.8:1.
  • Cyclopolymers of alkyldiallylamine or of dialkyldiallylammonium such as the homopolymers or copolymers comprising, as main constituent of the chain, units corresponding to formula (PI) or (PII) :
  • -R 12 denotes a hydrogen atom or a methyl group
  • R 10 and R 11 independently of each other, denote an alkyl group containing from 1 to 6 carbon atoms, a hydroxyalkyl group in which the alkyl group contains 1 to 5 carbon atoms, a C 1 -C 4 amidoalkyl group; or alternatively R 10 and R 11 may denote, together with the nitrogen atom to which they are attached, heterocyclic groups such as piperidyl or morpholinyl; R 10 and R 11 , independently of each other, preferably denote an alkyl group containing from 1 to 4 carbon atoms;
  • -Y - is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate or phosphate.
  • R 13 , R 14 , R 15 and R 16 which may be identical or different, represent aliphatic, alicyclic or arylaliphatic groups comprising from 1 to 20 carbon atoms or C 1-4 hydroxyalkylaliphatic groups, or else R 13 , R 14 , R 15 and R 16 , together or separately, form, with the nitrogen atoms to which they are attached, heterocycles optionally comprising a second heteroatom other than nitrogen, or else R 13 , R 14 , R 15 and R 16 represent a linear or branched C 1 -C 6 alkyl group substituted by a nitrile, ester, acyl, amide or -CO-O-R 17 -D or -CO-NH-R 17 -D group, where R 17 is an alkylene and D a quaternary ammonium group;
  • -A 1 and B 1 represent divalent polymethylene groups comprising 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 sulfur atoms or sulfoxide, sulfone, disulfide, amino, alkylamino, hydroxyl, quaternary ammonium, ureido, amide or ester groups, and
  • a 1 , R 13 and R 15 can form, with the two nitrogen atoms to which they are attached, a piperazine ring.
  • a 1 denotes a saturated or unsaturated and linear or branched alkylene or hydroxyalkylene group
  • B 1 can also denote a (CH 2 ) n -CO-D-OC- (CH 2 ) n -group in which D denotes:
  • a glycol residue of formula -O-Z-O- in which Z denotes a linear or branched hydrocarbon-based group, or a group corresponding to one of the following formulae: - (CH 2 -CH 2 -O) x -CH 2 -CH 2 -and - [CH 2 -CH(CH 3 ) -O] y -CH 2 -CH (CH 3 ) -, 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;
  • a bissecondary diamine residue such as a piperazine derivative
  • Y denotes a linear or branched hydrocarbon-based group, or else the divalent group -CH 2 -CH 2 -S-S-CH 2 -CH 2 -;
  • X - is an anion, such as chloride or bromide.
  • Mn number-average molar mass
  • -R 18 , R 19 , R 20 and R 21 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 group, where p is equal to 0 or to an integer of between 1 and 6, with the proviso that R 18 , R 19 , R 20 and R 21 do not simultaneously represent a hydrogen atom,
  • -r and s which may be identical or different, are integers between 1 and 6,
  • -q is equal to 0 or to an integer between 1 and 34
  • -A denotes a radical of a dihalide or preferably represents -CH 2 -CH 2 -O-CH 2 -CH 2 -.
  • Polyamines such as H sold by Cognis, referred to under the name Polyethylene glycol (15) tallow polyamine in the CTFA dictionary.
  • these polymers may be chosen in particular from homopolymers or copolymers comprising one or more units derived from vinylamine and optionally one or more units derived from vinylformamide.
  • K and M may also denote a cationic polymer chain comprising primary, secondary, tertiary or quaternary amine groups, in which at least one of the amine groups bears a carboxylic or sulphonic group linked via a hydrocarbon-based radical, or alternatively K and M form part of a chain of a polymer containing a ⁇ , ⁇ -dicarboxylic ethylene unit in which one of the carboxylic groups has been made to react with a polyamine comprising one or more primary or secondary amine groups.
  • amphoteric polymers corresponding to the above definition that are more particularly preferred are chosen from the following polymers:
  • a monomer derived from a vinyl compound bearing a carboxylic group such as, more particularly, acrylic acid, methacrylic acid, maleic acid, ⁇ -chloroacrylic acid
  • a basic monomer derived from a substituted vinyl compound containing at least one basic atom such as, more particularly, dialkylaminoalkyl methacrylate and acrylate, dialkylaminoalkylmethacrylamide and -acrylamide.
  • the vinyl compound may also be a dialkyldiallylammonium salt such as dimethyldiallylammonium chloride.
  • the copolymers of acrylic acid and of the latter monomer are sold under the names Merquat 280, Merquat 295 and Merquat Plus 3330 by the company Nalco.
  • the units derived from a monomer of (meth) acrylate or (meth) acrylamide type (i) are units of structure (Ia) below:
  • R 1 denotes H or CH 3 and R 2 is chosen from a -O-(CH 2 ) p -CH 3 radical with p being an integer preferably from 0 to 3, and more preferably 0 or 1, amino, dimethylamino, tert-butylamino, dodecylamino or -NH-CH 2 OH radical.
  • the said amphoteric polymer comprises a repetition of only one unit of formula (Ia) .
  • the unit derived from a monomer of (meth) acrylate or (meth) acrylamide type of formula (Ia) in which R 1 denotes H and R 2 is -O-CH 3 is particularly preferred. It corresponds to the monomer methylacrylate.
  • the units derived from a monomer of (meth) acrylamidoalkyltrialkylammonium type (ii) are units of structure (IIa) below:
  • -R 3 denotes H or CH 3 ,
  • -R 4 denotes a group (CH 2 ) k with k being an integer ranging from 1 to 6 and preferably from 2 to 4 , even more preferably 3;
  • R 5 -R 5 , R 6 and R 7 which may be identical or different, denote an alkyl group containing from 1 to 4 carbon atoms;
  • -Y- is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate or phosphate.
  • the said amphoteric polymer comprises a repetition of only one unit of formula (IIa) .
  • the units derived from a monomer of (meth) acrylic acid type (iii) are units of formula (IIIa) :
  • R 8 denotes H or CH 3 and R 9 denotes a hydroxyl radical or a –NH-C (CH 3 ) 2 -CH 2 -SO 3 H radical.
  • the preferred units of formula (IIIa) correspond to the acrylic acid, methacrylic acid and 2-acrylamino-2-methylpropanesulfonic acid monomers.
  • the unit derived from a monomer of (meth) acrylic acid type of formula (IIIa) is that derived from acrylic acid, for which R 8 denotes a hydrogen atom and R 9 denotes a hydroxyl radical.
  • the acidic monomer (s) of (meth) acrylic acid type may be non-neutralized or partially or totally neutralized with an organic or mineral base.
  • the said amphoteric polymer comprises a repetition of only one unit of formula (IIIa) .
  • the amphoteric polymer (s) of this type comprise at least 5 mol%of units derived from a monomer of (meth) acrylate or (meth) acrylamide type (i) .
  • they comprise from 5 mol%to 30 mol%and more preferably from 10 mol%to 20 mol%of units derived from a monomer of (meth) acrylamide type.
  • the content of units derived from a monomer of (meth) acrylamidoalkyltrialkylammonium type (ii) may advantageously be from 10 mol%to 60 mol%and preferentially from 20 mol%to 55 mol%.
  • the content of units derived from an acidic monomer of (meth) acrylic acid type (iii) may advantageously be from 20 mol%to 70 mol%and preferentially from 30 mol%to 60 mol%.
  • amphoteric polymer of this type comprises:
  • Amphoteric polymers of this type may also comprise additional units, other than the units derived from a monomer of (meth) acrylamide type, of (meth) acrylamidoalkyltrialkylammonium type and of (meth) acrylic acid type as described above.
  • the said amphoteric polymers consist solely of units derived from monomers (i) of (meth) acrylate type, (ii) of (meth) acrylamidoalkyltrialkylammonium type and (iii) of (meth) acrylic acid type.
  • amphoteric polymers that are particularly preferred, mention may be made of methyl acrylate/methacrylamidopropyltrimethylammonium chloride/acrylic acid terpolymers. Such polymers are listed in the CTFA Dictionary (International Cosmetic Ingredient Dictionary) under the name Polyquaternium 47. Corresponding products are especially sold under the names 2001 by the company Nalco.
  • amphoteric polymer As another type of amphoteric polymer that may be used, mention may also be made of copolymers based on (meth) acrylic acid and on a dialkyldiallylammonium salt, such as copolymers of (meth) acrylic acid and of dimethyldiallylammonium chloride.
  • An example that may be mentioned is 280 sold by the company Nalco.
  • R 4 represents a divalent radical derived from a saturated dicarboxylic acid, a mono-or dicarboxylic aliphatic acid containing an ethylenic double bond, an ester of a lower alkanol, having 1 to 6 carbon atoms of these acids or a radical derived from the addition of any one of said acids to a bis (primary) or bis (secondary) amine
  • Z denotes a bis (primary) , mono-or bis (secondary) polyalkylene-polyamine radical and preferably represents:
  • a difunctional crosslinking agent chosen from epihalohydrins, diepoxides, dianhydrides and bis-unsaturated derivatives
  • the saturated carboxylic acids are preferably chosen from acids having 6 to 10 carbon atoms, such as adipic acid, 2, 2, 4-trimethyladipic acid and 2, 4, 4-trimethyladipic acid, terephthalic acid and acids containing an ethylenic double bond such as, for example, acrylic acid, methacrylic acid and itaconic acid.
  • the alkane sultones used in the alkylation are preferably propane sultone or butane sultone, and the salts of the alkylating agents are preferably the sodium or potassium salts.
  • R 5 denotes a polymerizable unsaturated group such as an acrylate, methacrylate, acrylamide or methacrylamide group
  • y and z represent an integer from 1 to 3
  • R 6 and R 7 represent a hydrogen atom, methyl, ethyl or propyl
  • R 8 and R 9 represent a hydrogen atom or an alkyl radical such that the sum of the carbon atoms in R 8 and R 9 does not exceed 10.
  • the polymers comprising such units may also comprise units derived from non-zwitterionic monomers such as dimethyl or diethylaminoethyl acrylate or methacrylate, or alkyl acrylates or methacrylates, acrylamides or methacrylamides, or vinyl acetate.
  • non-zwitterionic monomers such as dimethyl or diethylaminoethyl acrylate or methacrylate, or alkyl acrylates or methacrylates, acrylamides or methacrylamides, or vinyl acetate.
  • R 10 represents a radical of formula:
  • R 11 , R 12 and R 13 which may be identical or different, each represent a hydrogen atom, a methyl, hydroxyl, acetoxy or amino residue, a monoalkylamine residue or a dialkylamine residue which are optionally interrupted by one or more nitrogen atoms and/or optionally substituted with one or more amine, hydroxyl, carboxyl, alkylthio or sulphonic groups, an alkylthio residue in which the alkyl group bears an amino residue, at least one of the radicals R 11 , R 12 and R 13 being, in this case, a hydrogen atom;
  • R 11 , R 12 and R 13 each represent a hydrogen atom, as well as the salts formed by these compounds with bases or acids.
  • R 14 represents a hydrogen atom, a CH 3 O, CH 3 CH 2 O or phenyl radical
  • R 15 denotes hydrogen or a lower alkyl radical such as methyl or ethyl
  • R 16 denotes hydrogen or a lower alkyl radical such as methyl or ethyl
  • R 17 denotes a lower alkyl radical such as methyl or ethyl or a radical corresponding to the formula: -R 18 -N (R 16 ) 2
  • R 18 representing a -CH 2 -CH 2 -, -CH 2 -CH 2 -CH 2 -or -CH 2 -CH (CH 3 ) -group, R 16 having the meanings mentioned above,
  • Amphoteric polymers of the type -D-X-D-X-chosen from:
  • E or E’ , E or E’ which may be identical or different, denoting a divalent radical which is an alkylene radical with a straight or branched chain containing up to 7 carbon atoms in the main chain, which is unsubstituted or substituted with hydroxyl groups and which can contain, in addition to the oxygen, nitrogen and sulphur atoms, 1 to 3 aromatic and/or heterocyclic rings; the oxygen, nitrogen and sulphur atoms being present in the form of ether, thioether, sulphoxide, sulphone, sulphonium, alkylamine or alkenylamine groups, hydroxyl, benzylamine, amine oxide, quaternary ammonium, amide, imide, alcohol, ester and/or urethane groups;
  • E denotes the symbol E or E’ and at least once E’ ;
  • E having the meaning given above and E’ being a divalent radical which is an alkylene radical with a straight or branched chain having up to 7 carbon atoms in the main chain, which is unsubstituted or substituted with one or more hydroxyl radicals and containing one or more nitrogen atoms, the nitrogen atom being substituted with an alkyl chain which is optionally interrupted by an oxygen atom and necessarily containing one or more carboxyl functions or one or more hydroxyl functions and betainized by reaction with chloroacetic acid or sodium chloroacetate.
  • (9) (C 1 -C 5 ) alkyl vinyl ether/maleic anhydride copolymers partially modified by semiamidation with an N, N-dialkylaminoalkylamine such as N, N-dimethylaminopropylamine or by semiesterification with an N, N-dialkanolamine.
  • These copolymers can also contain other vinyl comonomers such as vinylcaprolactam.
  • amphoteric polymers that are particularly preferred according to the invention are those of family (2) .
  • composition of the invention preferably contains said cationic and amphoteric polymer (s) in a total amount ranging from 0.01 to 5%by weight, preferably from 0.05 to 2.5%by weight, with regard to the total weight of the composition.
  • cationic surfactants used in the composition of the present invention correspond to the general formula (I) below:
  • radicals R 1 to R 4 which may be identical or different, represent a linear or branched aliphatic radical comprising from 1 to 30 carbon atoms, or an aromatic radical such as aryl or alkylaryl, with at least one of the radicals R 1 to R 4 denoting a linear or branched alkyl radical comprising from 10 to 30 carbon atoms, and X - denoting an organic or inorganic anion.
  • the aliphatic radicals may include heteroatoms such as, in particular, oxygen, nitrogen, sulfur and halogens.
  • the aliphatic radicals can be selected for example from C 1-30 alkyl, C 1-30 alkoxy, polyoxyalkylene (C 2 -C 6 ) , C 1-30 alkylamide, alkyl (C 12 -C 22 ) amidoalkyl (C 2 -C 6 ) and C 1-30 hydroxyalkyl radicals.
  • X is an anion selected from the group of halides, phosphates, acetates, lactates, alkyl (C 2 -C 6 ) sulfates and alkyl-or alkylaryl-sulfonates.
  • tetraalkylammonium chlorides such as, for example, dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl radical comprises approximately from 12 to 22 carbon atoms, more particularly behenyltrimethylammonium, distearyldimethylammonium, cetyltrimethylammonium, and benzyl-dimethylstearylammonium chlorides, or else, secondly, to palmitylamidopropyltrimethylammonium chloride or stearamidopropyldimethyl (myristyl acetate) -ammonium chloride, which is sold under the name 70 by the company Van Dyk.
  • tetraalkylammonium chlorides such as, for example, dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl radical comprises approximately from 12 to 22 carbon atoms, more particularly behenyltrimethylammonium, distearyldimethylammonium, cet
  • the cationic surfactants of formula (I) may be present in the composition of the present invention in an amount ranging from 0.01 to 10%by weight more preferably from 0.05 to 5%by weight, even more preferably from 0.1 to 2%by weight, relative to the total weight of the composition.
  • composition of the invention comprises as non-ionic surfactant one or more oxyethylenated esters of fatty acid and of sorbitan.
  • fatty acid it is meant in a manner known per se a carboxylic acid containing from 8 to 30 carbon atoms.
  • Said esters are typically chosen from oxyethylenated mono and polyesters of C 8 to C 30 fatty acids and of sorbitan having from 1 to 20 ethylene oxide units, and preferably from oxyethylenated mono and polyesters of C 12 to C 24 fatty acids and of sorbitan having from 4 to 20 ethylene oxide units.
  • Such compounds are known as Polysorbates. Among others, they are marketed under the name Tween.
  • Non-limiting examples of useful Polysorbates are the following ones: oxyethylenated sorbitan monolaurate with 4 OE (Polysorbate 21) , oxyethylenated sorbitan monolaurate with 20 OE (Polysorbate 20) , oxyethylenated sorbitan monopalmitate with 20 OE (Polysorbate 40) , oxyethylenated sorbitan monostearate with 20 OE (Polysorbate 60) , oxyethylenated sorbitan monostearate with 4 OE (Polysorbate 61) , oxyethylenated sorbitan tri stearate with 20 OE (Polysorbate 65) , oxyethylenated sorbitan monooleate with 20 OE (Polysorbate 80) , oxyethylenated sorbitan monooleate with 5 OE (Polysorbate 81) , and oxyeth
  • compound with X OE is understood to mean an oxyethylenated compound comprising an average number of X oxyethylene units per molecule.
  • oxyethylenated sorbitan monolaurate with 4 OE (Polysorbate 20) is particularly preferred.
  • the composition according to the invention preferably comprises at least 0.1%by weight of oxyethylenated esters of fatty acid and of sorbitan, relative to the total weight of the composition. Preferably, it comprises from 0.2 to 20%by weight, more preferably from 0.5 to 15%by weight, and even more preferably from 1 to 10%by weight of said esters, based on the total weight of the composition.
  • composition according to the invention advantageously comprises water, in a content of greater than or equal to 40%by weight relative to the total weight of composition.
  • the water content in the composition of the invention preferably ranges from 50%to 98%by weight, more preferentially from 80%to 95%by weight, relative to the total weight of the composition.
  • composition according to the invention may further comprise one or more water-soluble organic solvents (solubility of greater than or equal to 5%in water at 25°C and at atmospheric pressure) .
  • water-soluble organic solvents examples include linear or branched and preferably saturated monoalcohols or diols, comprising 2 to 10 carbon atoms, such as ethyl alcohol, isopropyl alcohol, hexylene glycol (2-methyl-2, 4-pentanediol) , neopentyl glycol and 3-methyl-1, 5-pentanediol, butylene glycol, dipropylene glycol and propylene glycol; aromatic alcohols such as phenylethyl alcohol; polyols containing more than two hydroxyl functions, such as glycerol; polyol ethers, for instance ethylene glycol monomethyl, monoethyl and monobutyl ether, propylene glycol or ethers thereof, for instance propylene glycol monomethyl ether; and also diethylene glycol alkyl ethers, especially C 1 -C 4 alkyl ethers, for instance diethylene glycol monoethyl ether or
  • composition according to the invention may further comprise one or more additives.
  • additives that may be used in accordance with the invention, mention may be made of polymers other than the cationic and amphoteric polymers described above such as anionic and nonionic polymers, surfactants other than the cationic and non-ionic surfactants described above, antidandruff agents, anti-seborrhoea agents, agents for preventing hair loss and/or for promoting hair regrowth, fatty substances, vitamins and provitamins including panthenol, sunscreens, mineral or organic pigments, sequestrants, plasticizers, solubilizers, acidifying agents, mineral or organic thickeners, especially polymeric thickeners, opacifiers or pearlizing agents, antioxidants, hydroxy acids, fragrances, preservatives, pigments and ceramides.
  • polymers other than the cationic and amphoteric polymers described above such as anionic and nonionic polymers, surfactants other than the cationic and non-ionic surfactants described above, antidandruff agents, anti-s
  • the above additives may generally be present in an amount, for each of them, of between 0 and 20%by weight relative to the total weight of the composition.
  • compositions of the invention are rinse-off or leave-in hair conditioners, and more preferably leave-in hair conditioners.
  • compositions according to the invention may be packaged in any suitable dispenser such as for example a jar, a tube, a pump-dispenser bottle or in an aerosol device, in particular a pump-dispenser.
  • compositions according to the invention may, when they are packaged in an aerosol device, contain at least one propellant.
  • the propellant can then be selected for example from dimethyl ether, C 3 to C 5 alkanes, halogenated hydrocarbons, and mixtures thereof.
  • the present invention also relates to a non-therapeutical process for treating keratin fibres, which consists in applying to the said fibres an effective amount of a composition as described above.
  • the composition may be removed it by rinsing.
  • the composition according to the invention is left on the hair, that is to say, not rinsed after its application.
  • composition may be applied to dry or damp keratin fibres.
  • the composition according to the invention is applied to keratin fibres, dry or damp, after applying a washing composition of the shampoo type.
  • compositions described above may be used on any type of hair: light or dark hair, natural hair or hair that has undergone a cosmetic treatment such as permanent waving, dyeing, bleaching or relaxing.
  • composition of the present invention is applied on sensitized hair.
  • the present invention finally relates to the use of a composition as described hereinbefore for conditioning keratin fibres and in particular hair.
  • keratin fibres means human keratin fibres and more specifically hair.
  • the invention and comparative formulas were manufactured into pump bottles, and were tested as leave-in sprays on dried swatches, and evaluation scores were given by 5 panellists, on the following properties:
  • -usage quality i.e., composition that is easily applied and spread along the hair shafts.
  • each panellist gave a score ranging from 1 to 5, representing:
  • the invention formula has an excellent long lasting cosmetic properties on the hair, very easily spread along the hair shaft.
  • the hair treated by the invention formula shows an improved light and natural feeling. Consequently, the hair after treating with the invention formula was neither greasy or sticky, nor lank or heavy.

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Abstract

L'invention concerne une composition pour le traitement de fibres de kératine comprenant : une ou plusieurs huile(s) de silicone ; un ou plusieurs polymère(s) choisi parmi les polymères cationiques et les polymères amphotères ; un ou plusieurs agent(s) tensioactif cationique(s) correspondant à la formule générale (I) ; et un ou plusieurs tensioactif(s) non-ionique(s) choisis entre des esters d'acide gras oxyéthylénés et le sorbitane. La composition est utilisable pour le conditionnement de fibres de kératine et en particulier des cheveux.
PCT/CN2015/091214 2015-09-30 2015-09-30 Composition pour le traitement de fibres de kératine WO2017054170A1 (fr)

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PCT/CN2015/091214 WO2017054170A1 (fr) 2015-09-30 2015-09-30 Composition pour le traitement de fibres de kératine

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CN109988261B (zh) * 2019-04-03 2021-02-12 南华大学 一种含脲基大环的环化聚合物及其制备方法和应用
FR3109527B1 (fr) * 2020-04-24 2022-03-25 Oreal Procédé de traitement des fibres kératiniques mettant en œuvre une composition comprenant au moins un alcoxysilane de formule (I), au moins une silicone non aminée de formule (II) ayant une masse moléculaire moyenne en poids inférieure ou égale à 1500 g/mol et au moins un agent colorant.

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6399050B1 (en) * 1999-06-18 2002-06-04 L'oreal S.A. Hair cosmetic composition in the form of a water-in-silicone emulsion comprising at least one fixing polymer
US20040062740A1 (en) * 2002-09-27 2004-04-01 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Stable cosmetic sprayable products with a desirable narrow conical spray pattern
US20040120914A1 (en) * 2002-06-28 2004-06-24 L'oreal Composition containing a quaternary silicone, a cation and two cationic polymers and method of use
US20050175568A1 (en) * 2004-02-10 2005-08-11 The Procter & Gamble Company Conditioning compositions comprising hydrophobically modified crosslinked cationic thickening polymers
US20090074695A1 (en) * 2007-09-14 2009-03-19 Veronique Mahe Cosmetic compositions comprising at least one cationic copolymer, at least one amino silicone and at least one cationic polymer, and methods of use thereof

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Publication number Priority date Publication date Assignee Title
JP2013514273A (ja) * 2009-12-18 2013-04-25 ロレアル ケラチン繊維を処理する方法

Patent Citations (5)

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Publication number Priority date Publication date Assignee Title
US6399050B1 (en) * 1999-06-18 2002-06-04 L'oreal S.A. Hair cosmetic composition in the form of a water-in-silicone emulsion comprising at least one fixing polymer
US20040120914A1 (en) * 2002-06-28 2004-06-24 L'oreal Composition containing a quaternary silicone, a cation and two cationic polymers and method of use
US20040062740A1 (en) * 2002-09-27 2004-04-01 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Stable cosmetic sprayable products with a desirable narrow conical spray pattern
US20050175568A1 (en) * 2004-02-10 2005-08-11 The Procter & Gamble Company Conditioning compositions comprising hydrophobically modified crosslinked cationic thickening polymers
US20090074695A1 (en) * 2007-09-14 2009-03-19 Veronique Mahe Cosmetic compositions comprising at least one cationic copolymer, at least one amino silicone and at least one cationic polymer, and methods of use thereof

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