WO2008041136A2 - Composition antifrisottis aqueuse pour les cheveux - Google Patents

Composition antifrisottis aqueuse pour les cheveux Download PDF

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Publication number
WO2008041136A2
WO2008041136A2 PCT/IB2007/004196 IB2007004196W WO2008041136A2 WO 2008041136 A2 WO2008041136 A2 WO 2008041136A2 IB 2007004196 W IB2007004196 W IB 2007004196W WO 2008041136 A2 WO2008041136 A2 WO 2008041136A2
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Prior art keywords
composition
chosen
fatty
weight
present
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PCT/IB2007/004196
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English (en)
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WO2008041136A3 (fr
Inventor
Nghi Van Nguyen
Sawa Hashimoto
David W. Cannel
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L'oreal
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Priority claimed from US11/544,484 external-priority patent/US8475778B2/en
Priority claimed from US11/544,481 external-priority patent/US20080085258A1/en
Priority claimed from US11/544,496 external-priority patent/US20080085255A1/en
Priority claimed from US11/544,495 external-priority patent/US20080085254A1/en
Application filed by L'oreal filed Critical L'oreal
Publication of WO2008041136A2 publication Critical patent/WO2008041136A2/fr
Publication of WO2008041136A3 publication Critical patent/WO2008041136A3/fr

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    • 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
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • A61K8/55—Phosphorus 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—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
    • A61K8/72—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • 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
    • A61K2800/5424—Polymers characterized by specific structures/properties characterized by the charge anionic
    • 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
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers

Definitions

  • Hair fibers depending on whether they are exposed to low or highly humid conditions, have a tendency to lose their shape, curl definition and/or become frizzy. These problems are the result of water loss or absorption from the fibers.
  • hair benefit agents such as cationic polymers are oftentimes incorporated into rinse-off hair products (shampoos, conditioners and the like) in order to seal in moisture within the hair fibers, thereby inhibiting water loss or absorption therefrom.
  • these hair benefit agents are rinsed off after their application onto the hair fibers.
  • the present invention is directed to a cosmetic composition, in particular a hair treatment composition, capable of inhibiting water loss or absorption from hair fibers upon exposure to both high and low humidity.
  • a cosmetic composition in particular a hair treatment composition, capable of inhibiting water loss or absorption from hair fibers upon exposure to both high and low humidity.
  • Such composition comprises:
  • At least one water-insoluble material chosen from non- anionic silicones, hydrocarbon oils, plant oils, fatty acids, fatty esters, fatty alcohols, fatty waxes, and mixtures thereof;
  • the present invention is also drawn to a process for inhibiting water loss or absorption from hair fibers upon exposure to both high and low humidity by contacting the hair fibers with the above-disclosed composition.
  • a hair treatment composition in accordance with the present invention due to its ability to carry oils and deliver them to hair, enables the hair to retain water when exposed to low humidity, and inhibit water absorption when exposed to high humidity.
  • the oils serve as a barrier, inhibiting water from escaping from, or entering into, the hair.
  • the cationic polymers are able to adhere more efficiently onto the hair, thereby reducing the likelihood of their being rinsed off of the hair during the shampooing process.
  • Constanting means imparting to at least one keratinous fiber at least one property chosen from combability, manageability, moisture-retentivity, luster, shine, and softness. The state of conditioning is evaluated by measuring, and comparing, the ease of combability of the treated hair and of the untreated hair in terms of combing work (gm-in) .
  • Form from means obtained from chemical reaction of, wherein “chemical reaction,” includes spontaneous chemical reactions and induced chemical reactions.
  • the phrase “formed from” is open ended and does not limit the components of the composition to those listed, e.g., as component (i) and component (ii) .
  • the phrase “formed from” does not limit the order of adding components to the composition or require that the listed components (e.g., components (i) and (ii) ) be added to the composition before any other components.
  • Hydrocarbons include alkanes, alkenes, and alkynes, wherein the alkanes comprise at least one carbon, and the alkenes and alkynes each comprise at least two carbons; further wherein the hydrocarbons may be chosen from linear hydrocarbons, branched hydrocarbons, and cyclic hydrocarbons; further wherein the hydrocarbons may optionally be substituted; and further wherein the hydrocarbons may optionally further comprise at least one heteroatom intercalated in the hydrocarbon chain.
  • Silicone compound includes, for example, silica, silanes, silazanes, siloxanes, and organosiloxanes; and refers to a compound comprising at least one silicon atom; wherein the silicone compound may be chosen from linear silicone compounds, branched silicone compounds, and cyclic silicone compounds; further wherein the silicone compound may optionally be substituted; and further wherein the silicone compound may optionally further comprise at least one heteroatom intercalated in the silicone chain, wherein the at least one heteroatom is different from the at least one silicon atom.
  • Substituted means comprising at least one substituent.
  • substituents include atoms, such as oxygen atoms and nitrogen atoms, as well as functional groups, such as hydroxyl groups, ether groups, alkoxy groups, acyloxyalkyl groups, oxyalkylene groups, polyoxyalkylene groups, carboxylic acid groups, amine groups, acylamino groups, amide groups, halogen containing groups, ester groups, thiol groups, sulphonate groups, thiosulphate groups, siloxane groups, and polysiloxane groups.
  • the substituent (s) may be further substituted.
  • Ethylene oxide group refers to a group of formula. -CH 2 CH 2 -O-.
  • Propylene oxide group as defined herein includes groups of formula -CH 2 CH 2 CH 2 -O-, groups of formula -(CHa)CHCH 2 -
  • Keratinous substrate as defined herein may be human keratinous fiber, and may be chosen from, for example, hair, eyelashes, and eyebrows, as well as the stratum corneum of the skin and nails.
  • Polymers include homopolymers and copolymers formed from at least two different types of monomers .
  • compositions of the present invention comprise at least one nitrogen-containing compound chosen from polyamine compounds having at least three amino groups, fatty monoamine compounds, fatty quaternary amine compounds, phospholipids, and mixtures thereof.
  • the polyamine compounds useful in the compositions of the present invention comprises at least three amino groups.
  • the composition of the present invention comprises at least one polyamine compound comprising at least four amino groups, such as greater than four amino groups.
  • the composition of the present invention comprises at least one polyamine compound comprising at least five amino groups, such as greater than five amino groups.
  • the composition of the present invention comprises at least one polyamine compound comprising at least six_ amino groups, such as greater than six amino groups.
  • the composition of the present invention comprises at least one polyamine compound comprising at least ten amino groups, such as greater than ten amino groups .
  • the composition of the present invention comprises at least one polyamine compound chosen from aminated polysaccharides comprising at least three amino groups, such as, for example, hydrolysates of aminated polysaccharides comprising greater than three amino groups.
  • the composition of the present invention comprises at least one polyamine compound chosen from polymers.
  • Suitable polymers are polymers comprising at least three amino groups as defined herein. Non-limiting examples of suitable polymers include homopolymers comprising at least three amino groups, copolymers comprising at least three amino groups, and terpolymers comprising at least three amino groups.
  • suitable polymers include, for example, polymers comprising at least three amino groups formed from (i) at least one monomer unit comprising at least one amino group as defined herein, and, optionally, (ii) at least one additional monomer unit different from the at least one monomer (i) ; and polymers comprising at least three amino groups formed from (i) at least one monomer comprising at least three amino groups as defined herein, and, optionally, (ii) at least one additional monomer unit different from the at least one monomer (i) .
  • the at least one additional monomer different from the at least one monomer (i) may or may not comprise at least one amino group as defined herein.
  • the composition of the present invention comprises at least one polyamine compound chosen from polyamines.
  • polyamine refers to a polymer comprising at least three repeating units, wherein each unit comprises at least one amino group as defined herein.
  • polyamines are chosen from polyethyleneimines .
  • Polyethyleneimines suitable for use in the compositions of the present invention may optionally be substituted.
  • Non-limiting examples of polyethyleneimines which may be used in the composition according to the present invention are the LupasolTM products commercially available from BASF.
  • Suitable examples of LupasolTM polyethyleneimines include LupasolTM PS, Lupasol PL, LupasolTM PR8515, LupasolTM G20, LupasolTM G35 as well as LupasolTM SC® Polythyleneimine Reaction Products (such as LupasolTM SC- ⁇ lB®, LupasolTM SC-62J®, and LupasolTM SC-86X®) .
  • Other non-limiting examples of polyethyleneimines which may be used in the composition according to the present invention are the EpominTM products commercially available from Aceto.
  • EpominTM polyethyleneimines include EpominTM SP-006, EpominTM SP-012, EpominTM SP-018, and EpominTM P- 1000.
  • Polyamines suitable for use in the present invention may also be chosen from polyvinylamines .
  • suitable polyvinylamines include Lupamines ® 9095, 9030, 9010, 5095, 1595 sold by BASF.
  • the polyamine compounds can also be substituted.
  • An example of such a compound is PEG-15 Cocopolyamine, sold by example by Cognis.
  • the composition of .the present invention comprises at least one polyamine compound comprising at least three amino groups chosen from proteins and protein derivatives.
  • suitable proteins and protein derivatives for use in the present invention include those listed at pages 1701 to 1703 of the CT. F.A. International Cosmetic Ingredient Dictionary and Handbook, 8 th edition, vol.2, (2000) .
  • Suitable protein include in particular wheat protein, soy protein, oat protein, collagen, and keratin protein.
  • the composition of the present invention does not comprise proteins and protein derivatives. In one embodiment, the composition of the present invention does not comprise compounds comprising lysine, compounds comprising arginine, and compounds comprising histidine. In one embodiment, the composition of the present invention comprises at least one polyamine compound comprising at least three amino groups, chosen from compounds comprising lysine, compounds, comprising arginine, compounds comprising histidine, and compounds comprising hydroxylysine.
  • the fatty monoamine compounds useful in the compositions of the present invention are monoamine compounds which contain at least one hydrocarbon group having from 6 to 22 carbon atoms.
  • Primary, secondary, and tertiary fatty monoamines are useful. Particularly preferred are tertiary amido amines having an alkyl group of from 6 to 22 carbon atoms.
  • Exemplary tertiary amido amines include: stearamidopropyldimethylamine, stearamidopropyldiethylamine, stearamidoethyldiethylamine, stearamidoethyldimethylamine, palmitamidopropyldimethyl amine, palmitamidopropyldiethylamine, palmitamidoethyldiethylamine, palmitamidoethyldimethylamine, behenamidopropyldimethylamine, behenamidopropyldiethylamine, behenamidoethyldiethylamine, behenamidoethyldimethylamine, arachnidamidopropyldimethylamine, arachidamidopropyldiethylamine, arachidamidoethyldiethylaitiine, arachidamidoethyldimethylamine, diethylamino
  • dimethylstearamine dimethylsoyamine, soyamine, myristylamine, tridecylamine, ethylstearylamine, N- tallowpropane diamine, hydroxylated, ethoxylated or propoxylated fatty amines such as ethoxylated stearylamine, dihydroxyethylstearylamine, and arachidylbehenylamine.
  • Further fatty monoamine compounds useful in the present invention are disclosed in U.S. Pat. No. 4,275,055.
  • the fatty quaternary amine compounds useful in the compositions of the present invention are quaternary amine compounds containing at least one long chain alkyl group.
  • Such long chain alkyl group preferably has from 6 to 22 carbon atoms .
  • the anion of the quaternary ammonium compound can be a common ion such as chloride, ethosulfate, methosulfate, acetate, bromide, lactate, nitrate, phosphate, or tosylate and mixtures thereof.
  • the long chain alkyl groups can include additional or replaced carbon or hydrogen atoms or ether linkages .
  • Other substitutions on the quaternary nitrogen can be hydrogen, benzyl or short chain alkyl or hydroxyalkyl groups such as methyl, ethyl, hydroxymethyl or hydroxyethyl, hydroxypropyl or combinations thereof.
  • fatty quaternary ammonium compounds include but are not limited to: behentrimonium chloride, cocotrimonium chloride, cethethyldimonium bromide, dibehenyldimonium chloride, dihydrogenated tallow benzylmonium chloride, disoyadimonium chloride, ditallowdimonium chloride, hydroxycetyl hydroxyethyl dimonium chloride, hydroxyethyl behenamidopropyl dimonium chloride, hydroxyethyl cetyldimonium chloride, hydroxyethyl tallowdimonium chloride, myristalkonium chloride, PEG-2 oleamonium chloride, PEG-5 stearmonium chloride, PEG-15 cocoyl quaternium 4, PEG-2 stearalkonium .4, lauryltrimonium chloride; quaternium-l ⁇ ; quaternium-18, lauralkonium chloride,
  • the phospholipids useful in the compositions of the present invention include in particular lecithins.
  • Lecithins are mixtures of phospholipids, i.e., diglycerides of fatty acids linked to an ester of phosphoric acid.
  • lecithins are diglycerides of stearic, palmitic, and oleic acids linked to the choline ester of phosphoric acid.
  • Lecithin is usually defined either as pure phosphatidyl cholines or as crude mixtures of phospholipids which include phosphatidyl choline, phosphatidyl serine, phosphatidyl ethanolamine, phosphatidyl inositol, other phospholipids, and a variety of other compounds such as fatty acids, triglycerides, sterols, carbohydrates, and glycolipids.
  • the lecithin used in the present invention may be present in the form of a liquid, a powder, or granules.
  • Lecithins useful in the invention include, but are not limited to, soy lecithin and hydroxylated lecithin.
  • ALCOLEC S which is a fluid soy lecithin
  • ALCOLEC F 100 which is a powder soy lecithin
  • ALCOLEC Z3 which is a hydroxylated lecithin, all of which are available from the American Lecithin Company.
  • additional examples of phospholipids which may be useful in the present invention include, but are not limited to, multifunctional biomimetic phospholipids.
  • the at least one nitrogen-containing compound is preferably present in a total amount of from greater than 0 to 30% by weight, preferably from greater than 0 to 10% by weight, and more preferably from greater than 0 to 5% by weight, based on the total weight of the composition.
  • the composition of the present invention also comprises at least one nonionic surfactant.
  • Preferred nonionic surfactants are those having a Hydrophilic-Lipophilic Balance (HLB) of from 8 to 20.
  • HLB Hydrophilic-Lipophilic Balance
  • Nonlimiting examples of nonionic surfactants useful in the compositions of the present invention are those disclosed for example in McCutcheon 1 s "Detergents and Emulsifiers, " North American Edition (1986), published by Allured Publishing Corporation; and McCutcheon' s "Functional Materials," North American Edition (1992); both of which are incorporated by reference herein.
  • nonionic surfactants useful herein include, but are not limited to, alkoxylated derivatives of the following compounds: fatty alcohols, alkyl phenols, fatty acids, fatty acid esters and fatty acid amides, wherein the fatty alkyl chain is in the Cs to C 50 range, preferably in the C12 to C 50 range, preferably in the Ci6 to C 40 range, more preferably in the C 24 to C 40 range, and having from 1 to 110 alkoxy groups.
  • the alkoxy groups are selected from the group consisting of C 2 to C 6 alkyl oxides and their mixtures, with ethylene oxide, propylene oxide, and their mixtures being the preferred alkoxides.
  • the alkyl chain may be linear, branched, saturated, or unsaturated.
  • the alkoxylated non-ionic surfactants the alkoxylated fatty alcohols are preferred, and the ethoxylated fatty alcohols and propoxylated alcohols are more preferred.
  • the alkoxylated fatty alcohols may be used alone or in mixtures thereof.
  • the alkoxylated fatty alcohols may also be used in mixtures with those alkoxylated materials disclosed herein-above.
  • ethoxylated fatty alcohols include laureth-3 (a lauryl ethoxylate having an average degree of ethoxylation of 3) , laureth-23 (a lauryl ethoxylate having an average degree of ethoxylation of 23) , ceteth-10 (a cetyl alcohol ethoxylate having an average degree of ethoxylation of 10) , steareth-10 (a stearyl alcohol ethoxylate having an average degree of ethoxylation of 10) , and steareth-2 (a stearyl alcohol ethoxylate having an average degree of ethoxylation of 2) , steareth-100 (a stearyl alcohol ethoxylate having an average degree of ethoxylation of 100) , beheneth-5 (a behenyl alcohol ethoxylate having an average degree of ethoxylation of 5) , beheneth-10 (a behenyl alcohol ethoxylate
  • Brij® nonionic surfactants sold by Uniqema, Wilmington, DE.
  • Brij® surfactants are the condensation products of aliphatic alcohols with from about 1 to about 54 moles of ethylene oxide, the alkyl chain of the alcohol being typically a linear chain and having from about 8 to about 22 carbon atoms, for example, Brij 72 (i.e., Steareth-2) and Brij 76 (i.e., Steareth-10).
  • alkyl (poly) glycosides which are the condensation products of long chain alcohols, preferably alcohols having from 8 to 30 carbon atoms, with sugar or starch polymers.
  • S is a sugar moiety such as glucose, fructose, mannose, galactose, and the like; n is an integer ranging from 1 to 1000, and R is a Cs to C 30 alkyl group.
  • R alkyl group examples include decyl alcohol, cetyl alcohol, stearyl alcohol, lauryl alcohol, myristyl alcohol, oleyl alcohol, and the like.
  • Preferred examples of these surfactants are alkyl (poly) glucosides wherein S is a glucose moiety, R is a Cs to C 2 o alkyl group, and n is an integer of from 1 to 9.
  • surfactants include decyl polyglucoside (available as APG® 325 CS) and lauryl polyglucoside (available as APG® 600CS and 625 CS) , all the above-identified polyglucosides are available from Cognis, Ambler, Pa. Also useful herein are sucrose ester surfactants such as sucrose cocoate and sucrose laurate.
  • glyceryl esters and polyglyceryl esters of fatty acids including but not limited to, glyceryl monoesters, preferably glyceryl monoesters of C16-C22 saturated, unsaturated and branched chain fatty acids such as glyceryl oleate, glyceryl monostearate, glyceryl monoisostearate, glyceryl monopalmitate, glyceryl monobehenate, and mixtures thereof, and polyglyceryl esters of C 16 -C2 2 saturated, unsaturated and branched chain fatty acids, such as polyglyceryl-4 isostearate, polyglyceryl-3 oleate, polyglyceryl-2 sesquioleate, triglyceryl diisostearate, diglyceryl monooleate, tetraglyceryl monooleate, and mixtures thereof.
  • glyceryl monoesters preferably glyceryl monoesters of C16-C22 saturated, uns
  • sorbitan esters of fatty acids are also useful herein as nonionic surfactants.
  • sorbitan esters include sorbitan monooleate (sold for example under the name SPAN® 80 by the company Sigma Aldrich) , sorbitan sesquioleate (sold for example under the name Arlacel® 83 by the company Uniqema, Wilmington DE) , sorbitan monoisostearate (sold for example under the name CRILL® 6 by the company Croda, Inc., Edison, N.J.) / sorbitan stearates
  • Sorbitan monoisostearate and sorbitan sesquioleate are particularly preferred nonionic surfactants for use in the present invention.
  • alkoxylated derivatives of the following compounds are alkoxylated derivatives of the following compounds: glyceryl esters of fatty acids, sorbitan esters of fatty acids, and alkyl (poly) glycosides, wherein the alkoxy groups is selected from the group consisting of C 2 -C 6 alkyl oxides and their mixtures, with ethoxylated or propoxylated derivatives of these materials being preferred.
  • Nonlimiting examples of commercially available ethoxylated sorbitan esters include the products sold under the name TWEEN® by the company ⁇ niqema and which are ethoxylated sorbitan mono-, di- and/or tri-esters of C 12 to Ci8 fatty acids with an average degree of ethoxylation of from about 2 to about 20.
  • Preferred nonionic surfactants are those formed from a fatty alcohol, a fatty acid, or a glyceride having a C 4 to C 36 carbon chain, preferably a C 12 to Ci ⁇ carbon chain, more preferably a Ci 6 to Ci ⁇ carbon chain, derivatized to yield an HLB of at least 8.
  • HLB is understood to mean the balance between the size and strength of the hydrophilic group and the size and strength of the lipophilic group of the surfactant.
  • Such derivatives can be polymers such as ethoxylates, propoxylates, polyglucosides, polyglycerins, polylactates, polyglycolates, polysorbates, and others r M_.ft ⁇ t u w ' oul'd be apparent to one of ordinary skill in the art.
  • Such derivatives may also be mixed polymers of the above, such as ethoxylate/propoxylate species, where the total HLB is preferably greater than or equal to 8.
  • the nonionic surfactants contain ethoxylate in a molar content of from 10- 25, more preferably from 10-20 moles.
  • the at least one nonionic surfactant is preferably present in the composition of the invention in an amount of from greater than 0 to 70% by weight, preferably from greater than 0 to 40% by weight, and more preferably from greater than 0 to 20% by weight, based on the total weight of the composition.
  • composition of the present invention also comprises at least one anionic silicone.
  • Non-limiting examples of anionic silicones which may be used in the present invention include silicone carboxylates, silicone phosphates, silicone sulfates, silicone sulfosuccinates, and silicone sulfonates.
  • Suitable silicone carboxylates may be chosen from water soluble silicone compounds comprising at least one carboxylic acid group, oil soluble silicone compounds comprising at least one carboxylic acid group, water- dispersible silicone compounds comprising at least one carboxylic acid group, and silicone compounds comprising at least one carboxylic acid group which are soluble in organic solvents.
  • the at least one silicone compound comprising at least one carboxylic acid group further comprises at least one alkoxylated chain, wherein the at least one alkoxy group may be chosen from terminal alkoxy groups, pendant alkoxy groups, and alkoxy groups which are intercalated in the skeleton of the at least one silicone compound.
  • Non-limiting examples of at least one alkoxy group include ethylene oxide groups and propylene oxide groups.
  • the at least one carboxylic acid group may be chosen from terminal carboxylic acid groups and pendant carboxylic acid groups. Further, the at least one carboxylic acid may be chosen from carboxylic acid groups in free acid form, i.e., - COOH, and carboxylic acid groups in salt form, i.e., -COOM, wherein M may be chosen from inorganic cations, such as, for example, potassium cations and sodium cations, and organic cations.
  • the at least one silicone compound comprising at least one carboxylic acid group is chosen from silicone compounds of formula (I) and salts thereof:
  • c, d, and e which may be identical or different, are each integers ranging from 0 to 20; EO is an ethylene oxide group; PO is a propylene oxide group; and R" is chosen from optionally substituted divalent hydrocarbons, such as alkylene groups and alkenylene groups comprising from 2 to 22 carbon atoms, and optionally substituted divalent aromatic groups, such as groups of formula (III):
  • Non-limiting examples of the at least one silicone compound include those commercially available from Noveon under the name Ultrasil ® CA-I Silicone and Ultrasil ® CA-2 Silicone, both of which correspond to formula (V) below.
  • This silicone carboxylate is sold in the free acid form as an emulsifier and dispersing aid for complexing fatty cationic amines and quaternary amines .
  • the at least one silicone compound is chosen from silicone compounds of formula
  • c, d, and e which may be identical or different, are each integers ranging from 0 to 20; EO is an ethylene oxide group; and PO is a propylene oxide group; x is an integer ranging from 0 to 60; R" is chosen from optionally substituted divalent hydrocarbons, such as alkylene groups and alkenylene groups comprising from 2 to 22 carbon atoms, and optionally substituted divalent aromatic groups, such as groups of formula (III) :
  • Non-limiting examples of the at least one silicone compound include those described in U.S. Patent Nos. 5,248,783 and 5,739,371, the disclosures of which are incorporated herein by reference, and which are silicone compounds of formula (I) .
  • Suitable silicone phosphates may be chosen from water-soluble silicone compounds comprising at least one phosphate group, oil soluble silicone compounds comprising at least one phosphate group, water-dispersible silicone compounds comprising at least one phosphate group, and silicone compounds comprising at least one phosphate group which are soluble in organic solvents.
  • the at least one silicone compound comprising at least one phosphate group further comprises at least one alkoxylated chain, wherein the at least one alkoxy group may be chosen from terminal alkoxy groups, pendant alkoxy groups, and alkoxy groups which are intercalated in the skeleton of the at least one silicone compound.
  • the at least one phosphate group may be chosen from terminal phosphate groups and pendant phosphate groups.
  • the at least one phosphate group may be chosen from groups of formula -O-P(O) (OH) 2 , groups of formula -0- P(O) (OH) (OR), and groups of formula -O-P(O) (OR) 2 , wherein R may be chosen from H, inorganic cations, and organic cations.
  • inorganic cations include alkali metals, such as, for example, potassium lithium, and sodium.
  • a non-limiting example of organic cations is at least one additional silicone compound which may be identical to or different from the at least one silicone compound bonded to the other oxygen of the phosphate group.
  • the at least one silicone compound comprising at least one phosphate group is chosen from silicone compounds of formula (I) :
  • R 1 which may be identical or different, are each chosen from H, organic cations, inorganic cations, optionally substituted hydrocarbons (such as alkyl groups and alkenyl groups comprising from 1 to 22 carbon atoms) , optionally substituted aromatic groups; groups of formula (II) and salts thereof:
  • c, and d which may be identical or different, are each integers ranging from 0 to 20; e is an integer ranging from 0 to 19; and x is an integer ranging from 0 to 21; groups of formula (III) and salts thereof:
  • c, d, and e which may be identical or different, are each integers ranging from 0 to 20; and x is an integer ranging from 0 to 21; and groups of formula (IV) and salts thereof: [0065] wherein: a is an integer ranging from 0 to 200; b is an integer ranging from 0 to 200; R' , which may be identical or different, are each chosen from optionally substituted hydrocarbons, such as alkyl groups and alkenyl groups comprising from 1 to 22 carbon atoms, optionally substituted aromatic groups, groups of formula (III) :
  • R which may be identical or different, are each chosen from optionally substituted hydrocarbons, such as alkyl groups and alkenyl groups comprising from 1 to 22 carbon atoms, optionally substituted aromatic groups, optionally substituted divalent hydrocarbons, such as alkylene groups and alkenylene groups comprising from 1 to 22 carbon atoms, optionally substituted divalent aromatic groups, groups of formula (III) :
  • the (CH 2 ) 3 end is bonded to the silicon of the compound of formula (IV) and the (EO) or (PO) end, if present, is bonded to the oxygen of the compound of formula (I);
  • c, d, and e which may be identical or different, are each integers ranging from 0 to 20;
  • EO is an ethylene oxide group;
  • PO is a propylene oxide group; and with the proviso that at least one R is chosen from groups of formula (V) and salts thereof; and with the further proviso that at least one R 1 is chosen from groups of formula (IV) and salts thereof and at least one other R 1 is chosen from H, organic cations, and inorganic cations .
  • Non-limiting examples of the inorganic cations include alkali metals, such as potassium, lithium, and sodium.
  • suitable silicone compounds comprising at least one phosphate group include those commercially available from the company Phoenix Chemical, Inc. of New Jersey under the name of Pecosil®, such as Pecosil® PS- 100, Pecosil® PS-112, Pecosil® PS-150, Pecosil® PS-200, Pecosil® WDS-100, Pecosil® WDS-200, Pecosil® PS-100 B, and Pecosil® PS-100 K, and those commercially available from the company Siltech under the name Silphos A-100 and Silphos A- 150.
  • Other non-limiting examples of suitable silicone compounds include those described in U.S. Patent Nos. 5,070,171, 5,093,452, and 5,149,765 the disclosures of which are incorporated herein by reference.
  • Suitable silicone sulfates for use in the present invention include those represented by formula (VI) :
  • R 11 is selected from lower alkyl having one to eight carbon atoms or phenyl
  • R 12 is - (CH 2 ) 3 -O- (EO) x - (PO) y - (EO) z —SO 3 -M wherein M is a cation and is selected from Na, K, Li, or NH 4 ;
  • x, y and z are integers independently ranging from 0 to 100;
  • R 13 is -(CH 2 ) 3 -0- (EO) x - (PO) y - (EO) 2 -H with x, y and z being integers independently ranging from 0 to 100;
  • R 14 is methyl or hydroxyl;
  • a 1 and c 1 are independently integers ranging from 0 to 50;
  • b 1 is an integer ranging from 1 to 50.
  • An example of corresponding available commercial product is the Ultrasil SA-I silicone sold by the company Noveon.
  • R represents a divalent radical selected from
  • a' and b' are integers ranging independently from 0 to 30; x and y are such that the molecular weight ranges from 700 to 1600, and M is an alkali metal such as sodium or potassium, or an ammonium group.
  • a particularly preferred anionic silicone is Dimethicone PEG-8 phosphate.
  • Dimethicone PEG-8 phosphate is for example commercially available from the company Noveon under the tradename Ultrasil PE-IOO.
  • the anionic silicone is advantageously present in the composition of the present invention in an amount ranging from greater than 0 to 50% by weight, preferably from greater than 0 to 30% by weight, and more preferably from greater than 0 to 15% by weight, based on the total weight of the composition.
  • the composition of the present invention also comprises at least one cationic polymer.
  • Preferred cationic polymers useful in the present invention are chosen from, but are not limited to, polyquaternium 4, polyquaternium 6, polyquaternium 7, polyquaternium 10, polyquaternium 11, polyquaternium 16, polyquaternium 22, polyquaternium 28, polyquaternium 32, guar hydroxypropyltrimonium chloride, and mixtures thereof.
  • Preferred cationic polymers include polyquaternium 10, polyquaternium 6 and guar hydroxypropyltrimonium chloride.
  • Corresponding commercially available products include for example: POLYMER JR-125, POLYMER JR-400, Polymer JR-30M hydroxyethyl cellulosic polymers (polyquaternium 10) available from Amerchol; JAGUAR C13-S (guar hydroxypropyltrimonium chloride) available from Rhodia; and MERQUAT 100 and 280, a dimethyl dialkyl ammonium chloride (polyquaternium 6) available from Nalco.
  • the cationic polymer is advantageously present the composition of the present invention in an amount of from greater than 0% to 15%, preferably from 0.5 to 10% by weight, and more preferably from 1 to 5% by weight, based on the total weight of the composition.
  • Film forming polymers useful in the composition of the present invention can be neutralized or partially neutralized polymers and resins such as, for example, those containing carboxyl moieties, such as acrylates and other carboxy polymers.
  • suitable water soluble film forming polymers include, for example, polyvinylpyrrolidone , polyvinylpyrrolidone / vinyl acetate, acrylates, polyesters, polyurethranes, polyimides, polysulfonates, guars, starches and the like.
  • water-insoluble polymers and resins have to be neutralized to about 90% of their carboxyl moieties to make them water soluble for the purpose of formulating products in aqueous solution and for the purpose of making products which have good non-build-up properties, i.e., can be easily washed off the hair after use.
  • Unneutralized or partially neutralized water- insoluble latexes can also be used as invention film-forming polymers. Included are the following latexes:
  • Acrylic acid/methacrylic acid/ acrylates/methacrylates copolymers such as the product sold under the name AMERHOLD DR-25 by the company Amerchol,
  • Acrylic acid/methacrylic acid/ acrylates /methacrylates /hydroxy ester acrylates copolymers such as the product sold under the name ACUDYNE 258 by the company Rohm & Haas.
  • the film forming polymer may be employed in an amount ranging from greater than 0 to 15% by weight, preferably from 0.5 to 10% by weight, and more preferably from 1 to 5% by weight, based on the total weight of the composition.
  • the water-insoluble ingredients for use in the present invention include: non-anionic silicones such as non- ionic, cationic and amino- silicones ranging from low molecular weight fluids to high molecular weight gums, including for example dimethicone, cyclomethicone, phenyl trimethicone, " dimethiconol, dimethicone copolyol, aminosilicone and laurylmethicone copolyol; hydrocarbon oils such as mineral oil, petrolatum, paraffins, iso-paraffins, aromatic hydrocarbons, and the like; plant oils such as olive, avocado, coconut, and the like; fatty acids; fatty esters; fatty alcohols; fatty waxes; and mixtures thereof.
  • the water-insoluble material may be employed in an amount ranging from greater than 0 to 30% by weight, preferably from greater than 0 to 15% by weight, and more preferably from greater than 0 to 5% by weight, based on the total weight of the composition.
  • compositions of the present invention may contain further water-insoluble materials or ingredients which can be chosen from, but are not limited to, the following: [0085] (1) Lipophilic "ingredients" or “materials” such as oil-soluble vitamins such as Vitamin E and Vitamin A, sunscreens, ceramides.
  • the lipophilic ingredients may be in the form of sunscreens, bacteriostats, moisturizers, colors, topical pharmaceuticals and the like.
  • Preferred lipophilic ingredients include: Vitamin E, Vitamin E Acetate, Vitamin A Palmitate, , 2-oleamido-l, 3-octadecanediol, octylmethoxy cinnamate, octyl salicylate, .
  • the lipophilic ingredients will, for example, moisturize or condition the skin, hair, and/or eyelashes and leave behind no oily feel;
  • compositions of the present invention may further contain additional ingredients.
  • Polar amino acids may be chosen from arginine, asparagine, aspartic acid (or aspartate), glutamine, glutamic acid (or glutamate) , histidine, lysine, serine, and threonine. These amino acids are hydrophilic due to their polar side chains. Lysine and arginine are positively charged at neutral pH, whereas histidine can be uncharged or positively charged depending on its local environment.
  • proteins, polypeptides or other natural extracts having a high polar amino acid content can be used as additional ingredients.
  • proteins having a major proportion of arginine units in the range from about 50 to about 90%, by weight, of the total protein
  • the protamine proteins are characterised by having: (a) a low molecular weight, in the range of about 5,000; (b) a high isoelectric point, in the pH range of about 10 to 12; and (c) a high arginine content, in the range from about 50 to about 90%, by weight of the total protein.
  • Proteins of high polar amino acid content as described above can be subjected to acid or base hydrolysis to yield polypeptides which also have a high polar amino acid content.
  • suitable polypeptides are also described in U.S. Pat. No. 3,997,659, being protamine-derived polypeptides having a molecular weight below about 5,000, a basic pH (10-12) , and an arginine content of about 50%, or greater, by weight of the total polypeptide.
  • proteins not only may naturally occurring proteins be used, but also synthetic proteins, for example, polylysine and polyarginine, or mixtures thereof.
  • An example of a suitable natural extract which is rich in arginine is aloe vera extract.
  • the polar amino acids and the proteins and polypeptides having a polar amino acid content of 50%, or greater are often isolated from natural sources in the form of salts and hydrosalts, which are also suitable for use according to the invention.
  • Such salts and hydrosalts are formed by reaction with mineral acids such as hydrochloric acid, phosphoric acid, carbonic acid, sulfuric acid, nitric acid, and the like, or the organic acids such as formic acid, acetic acid, lauric acid, chloroacetic acid and the like.
  • mineral acids such as hydrochloric acid, phosphoric acid, carbonic acid, sulfuric acid, nitric acid, and the like
  • organic acids such as formic acid, acetic acid, lauric acid, chloroacetic acid and the like.
  • a suitable example is arginine hydrochloride.
  • Preferred additional ingredients for use in the present invention are arginine and urea, as well as their respective salts and/or hydrosalts.
  • the amount of the abovementioned additional ingredients which may be employed in the present invention can range from greater than 0 to 10% by weight, preferably from
  • composition of the present invention preferably has a pH ranging from 2-12, preferably from 4 to 10, and more preferably from 5 to 8.
  • the present invention is also directed to a process for treating hair fibers, in particular for inhibiting hair fibers from absorbing and/or losing water in general, and especially when exposed to low or high humidity.
  • the process comprises contacting the hair fibers with the above-described composition.
  • Such contacting step can be followed by a rinsing step, after a leave-in time of between 10 seconds and 15 minutes
  • the present invention also concerns the use of the above-described composition for inhibiting hair fibers from absorbing and/or losing water. More preferably, the present invention concerns the use of the above-described composition as an anti-frizz composition.
  • This comparative example illustrates shampoo formulations containing a polyamine compound having at least three amino groups.
  • Procedure to make formulas I-IV In beaker A, add amount of phase A water and heat to 85 0 C with moderate mixing. Add PEI and Amphomer LV-71, if necessary, with high speed mixing. Mix well until uniform and clear. In beaker B, add Ultrasil PE-100, Procetyl AWS, and Olive oil, with moderate speed mixing. Heat to 85 0 C and mix well until uniform and clear. Next, add contents of beaker A into beaker B. Mix well and maintain at 85 0 C until uniform. If necessary, in beaker C, add amount of phase C water and with high speed mixing, sift in polymer JR-30. Mix well until it gels up. Add beaker C contents into phase A and B mixture above.
  • the TO reading or initial area of the hair, was taken by tracing the perimeter of the photocopied swatch and calculating the area of the hair using an image analysis software. These swatches were placed in the humidity chamber (90-95 %RH) for 4 hours. The T4 reading, was then taken as described above. The % change of the area of the swatches is calculated using the following calculation: (T4 - TO) /TO x 100, and the final results are averaged. The formulas that prevent frizz will be indicated by lower % change in the area,
  • This comparative example illustrates shampoo formulations containing a fatty monoamine.
  • Procedure to make formulas I-IV In beaker A, add amount of phase A water and heat to 85 0 C with moderate mixing. Add AMP and Amphomer LV-71, if necessary, with high speed mixing. Mix well until uniform and clear. In beaker B, add amount of phase B water and heat to 85 0 C with moderate mixing. At 85°C, add Lexamine S-13, Ultrasil PE-100, Procetyl AWS, and Olive oil, with high speed mixing. Mix well until uniform and clear. Next, add contents of beaker A into beaker B. Mix well and maintain at 85°C until uniform. If necessary, in beaker C, add amount of phase C water and with high speed mixing, sift in polymer JR-30.
  • the swatches After equilibrating at RT overnight, the swatches are unwound, then photocopied. TO, or initial area of the hair, was taken by tracing the perimeter of the photocopied swatch and calculating the area of the hair using an image analysis software. These swatches are hung in the humidity chamber (RH 90-95%) for 4 hours. After 4 hours, or at T4, the areas are again taken by photocopying the swatches, then tracing them and calculating the areas. The % change of the area of the swatches is calculated using the following calculation: (T4 - TO) /TO x 100, and the final results are averaged. The formulas that prevent frizz will be indicated by lower % change.
  • This comparative example illustrates shampoo formulations containing a fatty quaternary amine.
  • Procedure to make formulas I-IV In beaker A, add amount of phase A water and heat to 85 0 C with moderate mixing. Add AMP and Amphomer IN-Il 1 if necessary, with high speed mixing. Mix well until uniform and clear. In beaker B, add amount of phase B water and heat to 85 0 C with moderate mixing. At 85°C, add Behentrimonium Chloride, ⁇ ltrasil PE-100, Procetyl AWS, and Olive oil, with high speed mixing. Mix well until uniform and clear. Next, add contents of beaker A into beaker B. Mix well and maintain at 85 0 C until uniform.
  • phase C water and with high speed mixing, sift in polymer JR-30. Mix well until it gels up. Add beaker C contents into phase A and B mixture above. Mix well until uniform. Start cooling batch to RT. Reduce mixer speed to moderate speed and add SLES-2 and Cocamidopropyl Betaine. Gently mix to prevent aeration and cool to RT.
  • This comparative example illustrates shampoo formulations containing a lecithin.
  • Procedure to make formulas I-IV In beaker A, add amount of phase A water and heat to 85 0 C with moderate mixing. Add AMP and Amphomer IN-Il, if necessary, with high speed mixing. Mix well until uniform and clear. In beaker B, add amount of phase B water and heat to 85 0 C with moderate mixing. At 85 0 C, add Lecithin, Ultrasil PE-100, Procetyl AWS, and Olive oil, with high speed mixing. Mix well until uniform and clear. Next, add contents of beaker A into beaker B. Mix well and maintain at 85 0 C until uniform. If necessary, in beaker C, add amount of phase C water and with high speed mixing, sift in polymer JR-30.
  • the swatches After equilibrating at RT overnight, the swatches are unwound, then photocopied. TO, or initial area of the hair, was taken by tracing the perimeter of the photocopied swatch and calculating the area of the hair using an image analysis software. These swatches are hung in the humidity chamber (RH 90-95%) for 4 hours. After 4 hours, or at T4, the areas are again taken by photocopying the swatches, then tracing them and calculating the areas. The % change of the area of the swatches is calculated using the following calculation: (T4 - TO) /TO x 100, and the final results are averaged. The formulas that prevent frizz will be indicated by lower % change.

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Abstract

L'invention concerne une composition et un procédé empêchant les cheveux de friser lorsqu'ils sont exposés à une humidité élevée et/ou faible. La composition selon l'invention contient : (a) au moins un composé contenant de l'azote, choisi parmi des composés polyamine contenant au moins trois groupes amine, des composés monoamine gras, des composés amine quaternaires gras, des phospholipides et des mélanges de ceux-ci ; (b) au moins un tensio-actif non ionique ; (c) au moins une silicone anionique ; (d) au moins un matériau hydro-insoluble choisi parmi des silicones non anioniques, des huiles hydrocarbures, des huiles végétales, des acides gras, des esters gras, des alcools gras, des cires grasses, et des mélanges de ceux-ci ; (e) au moins un polymère cationique ; et (f) facultativement, au moins un polymère filmogène différent du polymère cationique au moins (e).
PCT/IB2007/004196 2006-10-06 2007-10-05 Composition antifrisottis aqueuse pour les cheveux WO2008041136A2 (fr)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US11/544,484 US8475778B2 (en) 2006-10-06 2006-10-06 Aqueous polyamine-containing anti-frizz composition for hair
US11/544,496 2006-10-06
US11/544,495 2006-10-06
US11/544,481 2006-10-06
US11/544,484 2006-10-06
US11/544,481 US20080085258A1 (en) 2006-10-06 2006-10-06 Aqueous polymaine-containing anti-frizz composition for hair
US11/544,496 US20080085255A1 (en) 2006-10-06 2006-10-06 Aqueous fatty monoamine-containing anti-frizz composition for hair
US11/544,495 US20080085254A1 (en) 2006-10-06 2006-10-06 Aqueous phospholipid-containing anti-frizz composition for hair

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2991580A1 (fr) * 2012-06-12 2013-12-13 Oreal Composition a rincer comprenant un polymere filmogene

Citations (7)

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US5332569A (en) * 1992-03-31 1994-07-26 Alberto-Culver Company Hair care composition for conditioning hair with silicone oil
US5362484A (en) * 1992-06-10 1994-11-08 Alberto-Culver Company Hair care composition for conditioning hair with silicone oil
US20040052748A1 (en) * 2002-09-06 2004-03-18 Vondruska Brian Jay Compositions of anionic polymeric rheology modifiers and cationic materials
EP1402881A1 (fr) * 2002-09-30 2004-03-31 L'oreal S.A. Compositions comprenant au moins une silicone phosphatée et au moins un composé aminé, et méthode utilisant ces compositions
EP1430870A2 (fr) * 2002-12-20 2004-06-23 L'oreal Compositions capillaires
WO2006065469A1 (fr) * 2004-12-16 2006-06-22 Noveon, Inc. Procede de preparation d’hydrocolloides
EP1733717A1 (fr) * 2005-06-16 2006-12-20 L'Oréal Systemes excipients aqueux pour matières insolubles dans l' eau

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5332569A (en) * 1992-03-31 1994-07-26 Alberto-Culver Company Hair care composition for conditioning hair with silicone oil
US5362484A (en) * 1992-06-10 1994-11-08 Alberto-Culver Company Hair care composition for conditioning hair with silicone oil
US20040052748A1 (en) * 2002-09-06 2004-03-18 Vondruska Brian Jay Compositions of anionic polymeric rheology modifiers and cationic materials
EP1402881A1 (fr) * 2002-09-30 2004-03-31 L'oreal S.A. Compositions comprenant au moins une silicone phosphatée et au moins un composé aminé, et méthode utilisant ces compositions
EP1430870A2 (fr) * 2002-12-20 2004-06-23 L'oreal Compositions capillaires
WO2006065469A1 (fr) * 2004-12-16 2006-06-22 Noveon, Inc. Procede de preparation d’hydrocolloides
EP1733717A1 (fr) * 2005-06-16 2006-12-20 L'Oréal Systemes excipients aqueux pour matières insolubles dans l' eau

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2991580A1 (fr) * 2012-06-12 2013-12-13 Oreal Composition a rincer comprenant un polymere filmogene
WO2013186715A3 (fr) * 2012-06-12 2014-05-22 L'oreal Composition de rinçage comprenant un polymère filmogène

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