WO2008047247A2 - Systèmes transporteurs aqueux pour produits insolubles dans l'eau - Google Patents

Systèmes transporteurs aqueux pour produits insolubles dans l'eau Download PDF

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WO2008047247A2
WO2008047247A2 PCT/IB2007/004263 IB2007004263W WO2008047247A2 WO 2008047247 A2 WO2008047247 A2 WO 2008047247A2 IB 2007004263 W IB2007004263 W IB 2007004263W WO 2008047247 A2 WO2008047247 A2 WO 2008047247A2
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composition
fatty
chosen
compound
water
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PCT/IB2007/004263
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English (en)
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WO2008047247A3 (fr
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Nghi Van Nguyen
Sawa Hashimoto
David W. Cannel
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L'oreal
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Priority claimed from US11/583,252 external-priority patent/US8728452B2/en
Priority claimed from US11/583,237 external-priority patent/US20080095725A1/en
Priority claimed from US11/583,419 external-priority patent/US20080095729A1/en
Priority claimed from US11/583,251 external-priority patent/US20080097070A1/en
Application filed by L'oreal filed Critical L'oreal
Publication of WO2008047247A2 publication Critical patent/WO2008047247A2/fr
Publication of WO2008047247A3 publication Critical patent/WO2008047247A3/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—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
    • 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
    • A61K8/55—Phosphorus compounds
    • A61K8/553—Phospholipids, e.g. lecithin
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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

Definitions

  • the present invention relates to a novel aqueous system based on a specific combination of compounds, wherein the aqueous system allows water-insoluble materials to be incorporated into aqueous solutions.
  • 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;
  • At least one carboxylic compound chosen from alkyl ether carboxylic acids, alkyl ether carboxylates, fatty acids having from about 6 to about 40 carbon atoms, and mixtures thereof; and
  • the present invention is also drawn to a process for treating a keratinous substrate comprising contacting the keratinous substrate with a composition as disclosed herein.
  • water-insoluble means those compounds which are either completely or partially insoluble in water, and, more precisely, which have a solubility in water at 25°C of less than 0,5% by weight.
  • amino groups as defined herein includes primary amino groups, secondary amino groups, and tertiary amino groups, and further includes amino groups which are terminal, pendant, and intercalated in a skeleton of the at least one polyamine compound, but does not, for example, include quaternary amino groups, amido groups, imino groups, nitrilo groups, or heteroatom analogs of any of the foregoing.
  • At least one as used herein means one or more and thus includes individual components as well as mixtures/combinations .
  • 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 -(CH 3 ) CHCH 2 - O-, and groups of formula -CH 2 (CH 3 )CH-O-.
  • 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 as defined herein, include homopolymers and copolymers formed from at least two different types of monomers .
  • the aqueous composition of the present invention enables water-insoluble materials or ingredients to be carried by the composition and yet provide a clear to substantially clear appearance. Surprisingly, the use of an alcohol is not required in order to render the composition clear to substantially clear in appearance. [0022]
  • the composition of the invention is easy to formulate and gentle on the hair, skin, or eyelashes because the surfactants used therein are generally mild.
  • the composition of the present invention readily delivers water-insoluble ingredients to the targeted keratinous substrate.
  • this composition can be used in the formulation of hair shampoos, conditioners, deep treatments, hair dyeing compositions, including oxidative dyes and bleaches, permanent waving compositions, curl relaxing compositions, hair setting compositions, bath and body products, sunscreens, cosmetics, skin moisturizers, and the like, all of which are homogeneous and clear to substantially clear in appearance.
  • composition can also be used to deliver active water-insoluble pharmaceutical ingredients, particularly in topical applications. Such systems could further help protect against oxidation and rancidity by protecting sensitive ingredients in pharmaceuticals or foods.
  • 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.
  • 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-61B®, 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.
  • Suitable examples of 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.
  • the composition of the present invention does not comprise compounds comprising lysine, compounds comprising arginine, and compounds comprising histidine.
  • 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, arachidamidoethyldiethylamine, arachidamidoethyldimethylamine, diethylaminoeth
  • 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-16; quaternium-18, lauralkonium chloride, olealkonium 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 following multifunctional biomimetic phospholipids manufactured by Uniqema Industries may be useful: cocamidopropyl PG-dimonium chloride phosphate (PHOSPHOLIPID PTC) , sodium coco PG-dimonium chloride phosphate (PHOSPHOLIPID CDM), stearamidopropyl PG-dimonium chloride phosphate (PHOSPHOLIPID SV) , sodium borageamidopropyl PG- dimonium chloride phosphate (PHOSPHOLIPID GLA) , and linoleamidopropyl PG-dimonium chloride phosphate (PHOSPHOLIPID EFA) .
  • 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'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 C 12 to C 50 range, preferably in the C16 to C 4 o 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 ⁇ 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 having an average degree of ethoxylation of e
  • 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 C 8 to C 30 alkyl group.
  • long chain alcohols from which the R alkyl group can be derived 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 20 alkyl group, and n is an integer of from 1 to 9.
  • Commercially available examples of these 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.
  • 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 C1 6 -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 C1 6 -C22 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 C1 6 -C
  • 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 Uniqema) , 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 (sold for example under the name SPAN® 60 by the company Uniqema) , sorbitan trioleate (sold for example under the name SPAN® 85 by the company Uniqema), sorbitan tristearate (sold for example under the name SPAN® 65 by the company Uniqema) , sorbitan dipalmitates (sold for example under the name SPAN® 40 by the company Uniqema), and sorbitan isostearate. Sorbitan monoisostearate.
  • 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 are 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 Uniqema and which are ethoxylated sorbitan mono-, di- and/or tri-esters of C 12 to Cis 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 Cis carbon chain, more preferably a C 16 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 that would 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-
  • 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
  • composition of the present invention contains at least one at least one carboxylic compound chosen from an alkyl ether carboxylic acid, an alkyl ether carboxylate, a Ce-
  • alkyl ether carboxylic acids or alkyl ether carboxylates useful in the present invention preferably correspond to formula (I):
  • R is a hydrocarbon radical containing from 6 to 40 carbon atoms; u, v and w, independently of one another, each represent a number of from 0 to 60; x, y and z, independently of one another, each represent a number of from 0 to 13;
  • R represents hydrogen or an alkyl group, the sum of x+y+z being > 0,
  • M is an alkali metal or alkaline earth metal (when compound (I) is an ether carboxylate) or hydrogen (when compound (I) is an ether carboxylic acid) .
  • Ether carboxylic acids or carboxylates corresponding to formula (I) can be obtained by alkoxylation of alcohols ROH with ethylene oxide as sole alkoxide or with several alkoxides and subsequent oxidation.
  • the numbers u, v, and w each represent the degree of alkoxylation. Whereas, on a molecular level, the numbers u, v and w and the total degree of alkoxylation can only be integers, including zero, on a macroscopic level they are mean values in the form of broken numbers .
  • R is linear or branched, acyclic or cyclic, saturated or unsaturated, aliphatic or aromatic, substituted or unsubstituted, preferably a linear or branched, acyclic C6-40 alkyl or alkenyl group or a Ci_ 40 alkyl phenyl group, more particularly a Cs- 22 alkyl or alkenyl group or a C4-18 alkyl phenyl group, more preferably a C12-1 8 alkyl group or alkenyl group or a C 6 -i 6 alkyl phenyl group; u, v, w, independently of one another, each preferably represent a number from 2 to 20, more preferably a number from 3 to 17 and most preferably a number from 5 to 15; x, y, z, independently of one another, each preferably represent a number from 0 to 13, more preferably a number from 1 to 10 and most preferably a number from 2
  • Suitable ether carboxylic acids or ether carboxylates include, but are not limited to, the following representatives referred to by their INCI names (INCI: nomenclature for raw materials according to the International Cosmetic Ingredient Dictionary, 7th Edition, published by the Cosmetic, Toiletry and Fragrance Association Inc. (CTFA), Washington D.
  • oleth-10 carboxylic acid laureth-5 carboxylic acid, laureth-11 carboxylic acid and mixtures thereof.
  • fatty acids having from about 6 to about 40 carbon atoms that may also be used as carboxylic compound (c) in the present invention correspond to formula (II):
  • R' ' is a hydrocarbon radical containing from 6 to 40 carbon atoms .
  • R' ' may be linear or branched, acyclic or cyclic, saturated or unsaturated, aliphatic or aromatic, substituted or unsubstituted, preferably a linear or branched, acyclic Ce- C 4 O alkyl or alkenyl group or a C 1 -C 40 alkyl phenyl group, more particularly a C8-C22 alkyl or alkenyl group or a C 4 -CiS alkyl phenyl group, more preferably a Ci 2 -Ci 8 alkyl group or alkenyl group or a C6-C16 alkyl phenyl group.
  • Suitable fatty acids having from about 6 to about 40 carbon atoms include, but are not limited to the following representatives referred to by their INCI names (INCI: nomenclature for raw materials according to the International Cosmetic Ingredient Dictionary, 10th Edition, published by the Cosmetic, Toiletry and Fragrance Association Inc. (CTFA), Washington D.
  • Particularly preferred fatty acids having from about 6 to about 40 carbon atoms include Capric Acid, Caprylic Acid, Why Acid, Oleic Acid, Isostearic Acid, and Stearic Acid.
  • the at least one carboxylic compound (c) is advantageously present in the composition of the invention in an amount of from greater than 0% to 50% by weight, preferably from greater than 0 to 30% by weight, more preferably from greater than 0 to 15% by weight, based on the total weight of the composition.
  • a homogeneous and clear to substantially clear aqueous composition can be formed capable of carrying up to about 50% by weight, based on the total weight of the composition, of water-insoluble compounds.
  • Suitable water-insoluble compounds for use in the present invention include, but are not limited to, the following:
  • Lipophilic compounds such as silicones, oil- soluble vitamins such as Vitamin E and Vitamin A, sunscreens, ceramides and natural oils.
  • the lipophilic compounds may be in the form of sunscreens, bacteriostats, moisturizers, colors, topical pharmaceuticals and the like.
  • Preferred lipophilic compounds include: vitamin E, vitamin E acetate, vitamin A palmitate, olive oil, mineral oil, 2-oleamido-l, 3- octadecanediol, octylmethoxy cinnamate, octyl salicylate, and silicones such as dimethicone, cyclomethicone, phenyl trimethicone, dimethiconol, dimethicone copolyol, aminosilicone and laurylmethicone copolyol.
  • the lipophilic compounds will, for example, moisturize or condition the skin, hair, and/or eyelashes and leave behind no oily feel.
  • Preferred water-insoluble compounds for use in the present invention include silicones ranging from low molecular weight fluids to high molecular weight gums; hydrocarbon oils such as mineral oil, petrolatum, paraffins, iso-paraffins, aromatic hydrocarbons, and the like; natural oils such as plant oils such as olive, avocado, coconut, and the like; synthetic oils; fatty acids; fatty esters; fatty alcohols; fatty waxes; and mixtures thereof.
  • fatty means comprising at least one fatty chain, ie a hydrocarbon chain comprising from 6 to 30 carbon atoms, preferably from 8 to 22 carbon atoms.
  • the water-insoluble compounds may be employed in an amount ranging from greater than 0 to 50% by weight, preferably from greater than 0 to 30% by weight, more preferably from greater than 0 to 20% by weight, most preferably from greater than 0 to 10% by weight, based on the total weight of the composition.
  • the composition can contain additional ingredients such as for example anionic surfactants, organic salts, inorganic salts, proteins, hair dyes, water-soluble polymers, quaternary ammonium compounds, complex and simple carbohydrates, amino acids, preservatives and fragrances.
  • the process for making the composition of the invention involves introducing the at least one nitrogen- containing compound, the at least one nonionic surfactant, the at least one carboxylic compound, and the at least one water- insoluble compound to an aqueous solution to form a diluted mixture. Heat may be optionally introduced at any stage of the preparation of the mixture and the final diluted mixture is allowed to cool.
  • the aqueous delivery system obtained can carry a high load (i.e., 50% by weight is considered a high load) of the water-insoluble compound.
  • the composition may further contain proteins including hydrolyzed soy protein, lauryldimonium hydrolyzed soy protein (cationic Soya protein) and wheat amino acids.
  • the proteins could also include corn, wheat, milk, or silk proteins, collagens, keratins, or others.
  • taurine and arginine hydrochloride may be associated therein to maximize protein binding to the keratinous substrate.
  • Cationic proteins or proteins in general may be stabilizers for the aqueous delivery system and enhance its delivery by changing the charge of the aqueous delivery system.
  • the skin and the hair attract cationic ingredients, and proteins are generally substantive to these tissues.
  • cationic polymers such as polyquaternium 4, polyquaternium 6, polyquaternium 7, polyquaternium 10, polyquaternium 11, polyquaternium 16, polyquaternium 22, and polyquaternium 32
  • cationic conditioners such as quaternium 27, behenamidopropyl PG-dimonium chloride, hydroxyethyl tallowdimonium chloride, hexadimethrine chloride, stearalkonium chloride, and cetrimonium chloride
  • isoparaffins sodium chloride, propylene glycol, preservatives such as phenoxyethanol, methylparaben, ethylparaben, and propylparaben
  • pH adjusters such as phosphoric acid, humectants such as trehalose, and emollients such as octyldodecanol .
  • materials from the classes listed above would be readily known to one of ordinary skill in the art.
  • composition of the present invention may be in the form of shampoos, conditioners (rinse-off and leave-in) , deep treatments for hair, body washes, bath gels, hair dyeing compositions, permanent wave formulations, relaxers, make-up preparations, particularly mascara and foundation, and skin creams or lotions.
  • Another embodiment of the present invention is drawn to a process for treating a keratinous substrate comprising contacting the keratinous substrate with an aqueous composition as described above. After such contacting step, the composition may optionally be removed, for example by rinsing .
  • the keratinous substrate includes but is not limited to, hair, skin, or eyelashes.
  • treating in the context of this invention includes, but is not limited to, shampooing, conditioning, dyeing, bleaching, permanent waving, relaxing, setting, moisturizing, and making-up, for example, applying mascara or foundation.
  • the present invention also concerns a personal care composition such as for example a shampoo, a conditioning composition, a dyeing composition, a bleaching composition, a permanent waving composition, a relaxing composition, a setting composition, a moisturizing composition, a making-up composition, comprising the composition as described above.
  • a personal care composition such as for example a shampoo, a conditioning composition, a dyeing composition, a bleaching composition, a permanent waving composition, a relaxing composition, a setting composition, a moisturizing composition, a making-up composition, comprising the composition as described above.
  • Such personal care composition shall then contain additional classical ingredients known from the man skilled in the art, and which depend on the use thereof.
  • composition of the present invention is particularly advantageous when used in shampoos, conditioners, and deep treatments for hair which has been treated, e.g., with color (dye or bleach) or chemicals (permanent wave or straightening), or hair which is dry or fine.
  • the present invention further includes a method for incorporating into an aqueous composition at least one water- insoluble compound, wherein a combination of the at least following compounds is used: (a) 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;
  • D.I. means deionised.
  • the complete system as shown in column A, is a clear system. It remains clear when diluted with water indefinitely. If one or two ingredients (PEI, nonionic surfactant or alkyl ether carboxylic acid) are removed from the formula, as shown in columns B to G, the mixtures are no longer clear; they are hazy and remain hazy when diluted with water.
  • PEI nonionic surfactant or alkyl ether carboxylic acid
  • This example illustrates the necessity of having all three components (PEI, nonionic surfactant and alkyl ether carboxylic acid) in order for the system to carry olive oil, and to still remain clear upon dilution with water.
  • the complete system is a clear system. It remains clear when diluted with water indefinitely. If one or two ingredients from the mixture (i.e, fatty amine, nonionic surfactant, or alkyl ether carboxylic acid) are removed from the formula, as shown in columns B to G, the mixtures are no longer clear; they are hazy and remain hazy when diluted with water.
  • one or two ingredients from the mixture i.e, fatty amine, nonionic surfactant, or alkyl ether carboxylic acid
  • This example illustrates the necessity of having all three components (fatty amine, nonionic surfactant, and alkyl ether carboxylic acid) in order for the system to carry olive oil, and to still remain clear upon dilution with water.
  • the complete system as shown in column A, is a clear system. It remains clear when diluted with water indefinitely. If one or two ingredients (ie, fatty quaternary amine, nonionic surfactant, or alkyl ether carboxylic) are removed from the formula, as shown in columns B to G, the mixtures are no longer clear; they are hazy and remain hazy when diluted with water.
  • one or two ingredients ie, fatty quaternary amine, nonionic surfactant, or alkyl ether carboxylic
  • This example illustrates the necessity of having all three components (ie, fatty quaternary amine, nonionic surfactant, and alkyl ether carboxylic) in order for the system to carry olive oil, and to still remain clear upon dilution with water.
  • the lecithin used in all examples 4 is sold by the company American Lecithin.
  • the complete system as shown in column A, is a clear system. It remains clear when diluted with water indefinitely. If one or two ingredients from the mixture (ie, lecithin, nonionic surfactant, or alkyl ether carboxylic acid) are removed from the formula, as shown in columns B to G, the mixtures are no longer clear; they are hazy and remain hazy when diluted with water.
  • one or two ingredients from the mixture ie, lecithin, nonionic surfactant, or alkyl ether carboxylic acid
  • This example illustrates the necessity of having all three components (lecithin, nonionic surfactant, and alkyl ether carboxylic acid) in order for the system to carry olive oil, and to still remain clear upon dilution with water.

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Abstract

La présente invention concerne une composition aqueuse contenant: (a) au moins un composé azoté choisi parmi les: composés polyamine portant au moins trois groupes amino, les composés monoamine gras, les composés amine quaternaire gras, les phospholipides et certains de leurs mélanges; (b) au moins un tensioactif non ionique; (c) au moins un composé carboxylique choisi parmi les acides carboxyliques d'alkyl-éther, les carboxylates d'alkyl-éther, les acides gras d'environ 6 à environ 40 atomes de carbone, et certains de leurs mélanges; et (d) au moins un produit insoluble dans l'eau. La composition est à la fois homogène et d'aspect limpide à sensiblement limpide.
PCT/IB2007/004263 2006-10-19 2007-10-17 Systèmes transporteurs aqueux pour produits insolubles dans l'eau WO2008047247A2 (fr)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US11/583,252 2006-10-19
US11/583,252 US8728452B2 (en) 2006-10-19 2006-10-19 Aqueous fatty monoamine-containing systems for water-insoluble materials
US11/583,237 US20080095725A1 (en) 2006-10-19 2006-10-19 Aqueous phospholipid-containing systems for water-insoluble materials
US11/583,237 2006-10-19
US11/583,419 US20080095729A1 (en) 2006-10-19 2006-10-19 Aqueous fatty quaternary amine-containing systems for water-insoluble materials
US11/583,419 2006-10-19
US11/583,251 US20080097070A1 (en) 2006-10-19 2006-10-19 Aqueous polyamine-containing systems for water-insoluble materials
US11/583,251 2006-10-19

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WO2008047247A3 WO2008047247A3 (fr) 2009-12-10

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2219591A2 (fr) * 2007-12-07 2010-08-25 The Procter & Gamble Company Shampooing contenant un réseau de gel
WO2012175688A3 (fr) * 2011-06-24 2013-12-12 L'oreal Composition colorante sous forme d'émulsion contenant une amine ou un phospholipide, au moins un tensioactif non ionique et au moins un acide carboxylique, et procédé de production de ladite composition

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0487958A1 (fr) * 1990-11-26 1992-06-03 Kao Corporation Composition cosmétique transparente ou semi-transparente
FR2755371A1 (fr) * 1996-11-07 1998-05-07 Oreal Composition cosmetique sous la forme d'un gel transparent moussant
US6143286A (en) * 1998-08-05 2000-11-07 Revlon Consumer Products Corporation Method for improving the fade resistance of hair and related compositions
US20030044435A1 (en) * 1996-12-31 2003-03-06 Griscom Bettle Skin product having continuing antimicrobial, antiviral, antiseptic, and healing properties
US20030144169A1 (en) * 2001-12-07 2003-07-31 The Procter & Gamble Company Anti-wrinkle silicone polysaccharde compounds and compositions comprising said compounds

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0487958A1 (fr) * 1990-11-26 1992-06-03 Kao Corporation Composition cosmétique transparente ou semi-transparente
FR2755371A1 (fr) * 1996-11-07 1998-05-07 Oreal Composition cosmetique sous la forme d'un gel transparent moussant
US20030044435A1 (en) * 1996-12-31 2003-03-06 Griscom Bettle Skin product having continuing antimicrobial, antiviral, antiseptic, and healing properties
US6143286A (en) * 1998-08-05 2000-11-07 Revlon Consumer Products Corporation Method for improving the fade resistance of hair and related compositions
US20030144169A1 (en) * 2001-12-07 2003-07-31 The Procter & Gamble Company Anti-wrinkle silicone polysaccharde compounds and compositions comprising said compounds

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2219591A2 (fr) * 2007-12-07 2010-08-25 The Procter & Gamble Company Shampooing contenant un réseau de gel
EP2219591B1 (fr) * 2007-12-07 2022-02-23 The Procter & Gamble Company Shampooing contenant un réseau de gel
WO2012175688A3 (fr) * 2011-06-24 2013-12-12 L'oreal Composition colorante sous forme d'émulsion contenant une amine ou un phospholipide, au moins un tensioactif non ionique et au moins un acide carboxylique, et procédé de production de ladite composition

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