EP1377258A2 - Wärmeaktivierte haarkonditionierungsmittel enthaltend saccharide und verwendung - Google Patents

Wärmeaktivierte haarkonditionierungsmittel enthaltend saccharide und verwendung

Info

Publication number
EP1377258A2
EP1377258A2 EP02733135A EP02733135A EP1377258A2 EP 1377258 A2 EP1377258 A2 EP 1377258A2 EP 02733135 A EP02733135 A EP 02733135A EP 02733135 A EP02733135 A EP 02733135A EP 1377258 A2 EP1377258 A2 EP 1377258A2
Authority
EP
European Patent Office
Prior art keywords
chosen
composition according
monosaccharides
quaternary ammonium
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP02733135A
Other languages
English (en)
French (fr)
Inventor
Nghi Nguyen
David W. Cannell
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US09/820,858 external-priority patent/US7459150B2/en
Priority claimed from US09/820,934 external-priority patent/US20020172650A1/en
Priority claimed from US09/821,111 external-priority patent/US6486105B1/en
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP1377258A2 publication Critical patent/EP1377258A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties
    • 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
    • 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 compositions, kits comprising these compositions, and methods for using these compositions for care, treatment or durable conditioning of at least one keratinous fiber, including human keratinous fibers, comprising (i) at least one compound comprising at least two quaternary ammonium groups, and (ii) at least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C s monosaccharides substituted with at least one C, to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group.
  • These compositions may be used to care for, treat and durably condition keratinous fibers.
  • Shampoos generally comprise surfactants, such as anionic surfactants, to clean the hair.
  • anionic surfactants not only remove the dirt and soil but also remove the naturally-present sebum from hair.
  • shampoos may leave the hair dull and dry, that is, with what is known in the art as "creak". This generally makes the hair extremely difficult to comb either wet or dry, and once dry, the hair may not be amenable to styling, and may have undesirable electrostatic properties, causing the hair to "fly away.” Due to the unsatisfactory condition of shampooed hair, many consumers use a conditioning composition to improve at least one of these undesirable characteristics.
  • Conditioning agents in the prior art include cationic compounds such as cationic surfactants and cationic polymers which may render the hair more manageable, at least temporarily.
  • cationic compounds such as cationic surfactants and cationic polymers which may render the hair more manageable, at least temporarily.
  • quaternized ammonium compounds may be used as hair conditioning agents. These compounds may be substantive to the hair due to the ionic interaction between their positive charge on the ammonium nitrogen atom and negative charges on the surface of the hair fibers. This ionic interaction, in effect, allows the conditioning agents to coat the hair shaft and thereby prevent tangling and matting of the individual hair fibers.
  • the ability of these cationic compounds to adsorb to and/or react with the keratinous material of the hair makes them desirable compounds for conditioning the hair, such as for detangling wet hair and imparting manageability to dry hair.
  • Conditioning agents may be comprised in a composition distinct from the shampoo composition or may be incorporated into the shampoo composition itself.
  • quaternized ammonium compounds have been included in compositions such as shampoos, conditioners and treatments that are normally applied to hair at room temperature.
  • the effect of these conditioning agents may not be long lasting. Normally, because of the weak ionic bond between the quaternized ammonium compounds and the hair fiber, the quaternized ammonium compounds are washed off the hair easily. This is especially true during shampooing, wherein anionic surfactants are present, generally in high concentrations.
  • the anionic surfactants in the shampoo and the cationic conditioning agents are known to form a complex which may be easily removed from the hair during the shampooing and/or which decreases the cleansing capabilities of the anionic surfactant and the conditioning capabilities of the conditioning agent.
  • Sugars and sugar derivatives are one class of the countless number of compounds that have been added to hair care compositions.
  • Documented uses of sugars in hair care compositions include: the use of glucose to improve the tactile and elastic properties of natural hair (Hollenberg and Mueller, SOFW J. 121(2) (1995)); the use of glucose for hair damage prophylaxis and damaged hair repair (Hollenberg & Matzik, Seifen. Oele. Fette. Wachase 117(1) (1991)); the use of glucose in shampoos (J04266812, assigned to Lion Corp.); the use of trehalose for moisture retention (J06122614, assigned to Shiseido Co. Ltd.); a composition for the lanthionization of hair comprising a sugar (U.S. Patent Nos.
  • the inventors have envisaged the application to at least one keratinous fiber of at least one composition comprising at least one compound comprising at least two quaternary ammonium groups and at least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C 5 monosaccharides substituted with at least one C, to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group.
  • the inventors have discovered that such compositions and methods using these compositions comprising applying them to at least one keratinous fiber and heating the at least one keratinous fiber, impart a durable conditioning to the at least one keratinous fiber.
  • the compositions of the invention may also be used to care for, or treat, the at least one keratinous fiber.
  • the present invention in one aspect, provides a composition, in particular for durable conditioning of at least one keratinous fiber comprising at least one compound comprising at least two quaternary ammonium groups and at least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C 5 monosaccharides substituted with at least one C to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group.
  • the at least one compound comprising at least two quaternary ammonium groups and at least one sugar are present in an amount effective to durably condition the at least one keratinous fiber.
  • the composition is heat-activated.
  • the present invention is drawn to a method for caring for or treating or for durable conditioning of at least one keratinous fiber comprising applying to the at least one keratinous fiber at least one compound comprising at least two quaternary ammonium groups and at least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C 5 monosaccharides substituted with at least one C, to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group and heating the at least one keratinous fiber, wherein the at least one sugar and at least one compound are present in an amount effective to care for or treat the at least one keratinous fiber, and further wherein the composition is applied prior to or during heating.
  • the present invention provides a kit for caring for, treating or durably conditioning at least one keratinous fiber.
  • the kit comprises at least two compartments, wherein a first compartment comprises a first composition comprising at least one compound comprising at least two quaternary ammonium groups, and wherein a second compartment comprises at least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C 5 monosaccharides substituted with at least one C, to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group.
  • at least one compartment comprises at least one additional sugar, different from the at least one compound.
  • the present invention provides a method for durably conditioning at least one keratinous fiber comprising applying to the at least one keratinous fiber a composition comprising at least one compound comprising at least two quaternary ammonium groups; rinsing the at least one keratinous fiber; applying to the at least one rinsed keratinous fiber a composition comprising at least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C 5 monosaccharides substituted with at least one C, to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group; and heating the at least one keratinous fiber, wherein the at least one sugar is present in the composition comprising at least one sugar chosen from C 3 to C 5 monosaccharides in an amount effective to durably condition the at least one rinsed keratinous fiber, and further wherein the composition comprising at least one sugar chosen from C 3 to C 5 monosaccharides is applied prior to or during the heating
  • At least one means one or more and thus includes individual components as well as mixtures/combinations.
  • Conditioning means imparting at least one of combability, manageability, moisture-retentivity, luster, shine, softness, and body to the hair.
  • “Durable conditioning” as used herein means that, following at least six shampoos after treatment, treated hair still remains in a more conditioned state as compared to untreated hair. The state of conditioning can be 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) and/or the substantivity of the conditioning agent on the hair (for example, see Example 8).
  • Heating refers to the use of elevated temperature (i.e. above 100°C).
  • the heating in the inventive method may be provided by directly contacting the at least one keratinous fiber with a heat source, e.g., by heat styling of the at least one keratinous fiber.
  • heat styling by direct contact with the at least one keratinous fiber include flat ironing, and curling methods using elevated temperatures (such as, for example, setting hair in curlers and heating, and curling with a curling iron and/or hot rollers).
  • the heating in the inventive method may be provided by heating the at least one keratinous fiber with a heat source which may not directly contact the at least one keratinous fiber.
  • heat sources which may not directly contact the at least one keratinous fiber include blow dryers, hood dryers, heating caps and steamers.
  • a heat-activated composition refers to a composition which, for example, conditions the at least one keratinous fiber better than the same composition which is not heated during or after application of the composition.
  • Another example includes a composition which cares for or treats at least one keratinous fiber better than the same composition which is not heated during or after application.
  • Keratinous fibers as defined herein may be human keratinous fibers, and may be chosen from, for example, hair.
  • Oletaccharides refers to compounds generally comprising from two to ten monosaccharide units, which may be identical or different, bonded together.
  • Polysaccharides as defined herein refers to compounds generally comprising greater than ten monosaccharide units, which may be identical or different, bonded together.
  • Polymers as defined herein comprise copolymers (including terpolymers) and homopolymers.
  • Quaternary ammonium groups as defined herein refers to both ammonium groups that are quaternized and to amine groups which are capable of being quaternized (such as appended amines).
  • sugars have been used in hair care compositions and other treatments for their moisture retaining properties.
  • a certain class of sugars in combination with a certain class of film forming compounds, had other properties that made them particularly desirable for use on keratinous fibers.
  • compositions comprising at least one compound comprising at least two quaternary ammonium groups and at least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C 5 monosaccharides substituted with at least one C, to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group were found to durably condition the hair and also found to be useful in caring for and treating the hair.
  • these compositions may impart to at least one keratinous fiber a durable conditioning even after shampooing the at least one keratinous fiber subsequent to treatment with a composition comprising at least one such compound. This is particularly true when the compositions are applied to the hair, and the hair is then heated.
  • the invention provides compositions in particular for durable conditioning of at least one keratinous fiber comprising (i) at least one compound comprising at least two quaternary ammonium groups and (ii) at least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C 5 monosaccharides substituted with at least one C, to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group.
  • the at least one compound and at least one sugar are present in an amount effective to condition the at least one keratinous fiber.
  • the composition is heat-activated.
  • the composition may further comprise at least one additional sugar.
  • the present invention also provides methods for caring for or treating at least one keratinous fiber comprising applying to the at least one keratinous fiber a composition comprising (i) at least one compound comprising at least two quaternary ammonium groups, and (ii) at least one sugar chosen from C 3 to C 5 monosaccharides; from C 3 to C 5 monosaccharides substituted with at least one C, to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group and heating the at least one keratinous fiber.
  • the composition may be applied prior to or during heating.
  • the at least one compound and the at least one sugar are present in an amount effective to care for or treat the at least one keratinous fiber, depending on the embodiment.
  • the composition both cares for and treats the at least one keratinous fiber.
  • the composition may further comprise at least one additional sugar.
  • the present invention also provides methods for durable conditioning of at least one keratinous fiber comprising applying to the at least one keratinous fiber a composition comprising (i) at least one compound comprising at least two quaternary ammonium groups, and (iiat least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C 5 monosaccharides substituted with at least one C, to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group; and heating the at least one keratinous fiber.
  • the composition may be applied prior to or during heating.
  • the at least one compound and the at least one sugar are preferably present in an amount effective to durably condition the at least one keratinous fiber, depending on the embodiment.
  • the composition may further comprise at least one additional sugar.
  • the present invention also provides a method for durably conditioning at least one keratinous fiber comprising applying to the at least one keratinous fiber a composition comprising at least one compound comprising at least two quaternary ammonium groups.
  • the at least one keratinous fiber is then rinsed, and a composition comprising at least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C 5 monosaccharides substituted with at least one C to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group is applied to the at least one keratinous fiber.
  • the at least one keratinous fiber is then heated prior to and/or during the application of the composition comprising at least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C 5 monosaccharides substituted with at least one C 1 to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group.
  • the at least one sugar is present preferably in the composition comprising at least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C 5 monosaccharides substituted with at least one C, to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group in an amount effective to durably condition the at least one rinsed keratinous fiber.
  • the at least one compound comprising at least two quaternary ammonium groups may be chosen from water soluble compounds, oil soluble compounds, and compounds soluble in organic solvents.
  • Non-limiting examples of the at least one compounds are those listed at pages 1703 to 1706 of the CTFA International Cosmetic Ingredient Dictionary, 8 th edition (2000).
  • the at least two quaternary ammonium groups may be identical or different.
  • Amine groups which are capable of being quaternized may be chosen from primary, secondary, and tertiary amines.
  • the at least two quaternary ammonium groups may be chosen from substituent ammonium groups (such as terminal ammonium groups and pendant ammonium groups), substituent amino groups capable of being quaternized (such as terminal amino groups capable of being quaternized and pendant amino groups capable of being quaternized), ammonium groups forming part of the skeleton of at least one compound and amino groups capable of being quaternized forming part of the skeleton of at least one compound.
  • the at least one compound comprising at least two quaternary ammonium groups may be chosen from, for example, polymers comprising at least two quaternary ammonium groups derived from (i) at least one monomer unit comprising at least two quaternary ammonium groups 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 two quaternary ammonium groups derived from (i) at least one monomer comprising at least one quaternary ammonium group 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 quaternary ammonium group as defined herein.
  • Non-limiting examples of monomers comprising at least one quaternary ammonium group as defined herein are vinyl monomers substituted with at least one group chosen from dialkylaminoalkyl acrylate, dialkylaminoalkyl methacrylate, monoalkylaminoalkyl acrylate, monoalkylaminoalkyl methacrylate, trialkyl methacryloxyalkyl ammonium salts, trialkyl acryloxyalkyl ammonium salts and diallyl quaternary ammonium salts; and vinyl quaternary ammonium monomers comprising at least one cyclic cationic nitrogen-containing ring (such as a pyridinium ring, an imidazolium ring, and a quaternized pyrrolidone ring).
  • cyclic cationic nitrogen-containing ring such as a pyridinium ring, an imidazolium ring, and a quaternized pyrrolidone ring.
  • Non-limiting examples of the at least one compound comprising at least two quaternary ammonium groups are copolymers derived from (i) vinyl monomers comprising at least one quaternary ammonium group as defined herein and (ii) at least one additional monomer chosen from acrylamide, methacrylamide, alkyl acrylamides, dialkyl acrylamides, alkyl methacrylamides, dialkyl methacrylamides, alkyl acrylate, alkyl methacrylate, vinyl caprolactone, vinyl pyrrolidone, vinyl esters, vinyl alcohol, maleic anhydride, propylene glycol, and ethylene glycol.
  • the at least one compound comprising at least two quaternary ammonium groups may be chosen from copolymers derived from (i) 1-vinyl-2-pyrrolidone and (ii) 1-vinyl-3-methylimidazolium salt (CTFA designation: polyquaternium-16), which is commercially available from BASF Corporation under the LUVIQUAT tradename (e.g., LUVIQUAT FC 370) and copolymers derived from (i) 1-vinyl-2-pyrrolidone and (ii) dimethylaminoethyl methacrylate, (CTFA designation: polyquatemium-11), which is commercially available from Gaf Corporation (Wayne, N.J., USA) under the GAFQUAT tradename (e.g., GAFQUAT 755N).
  • CTFA designation: polyquaternium-16 which is commercially available from BASF Corporation under the LUVIQUAT tradename (e.g., LUVIQUAT FC 370)
  • CTFA designation: polyquatemium-11
  • the at least one compound comprising at least two ammonium groups are optionally quaternized poly(vinylamine), which can be made by polymerizing vinylamine and optionally quaternizing, optionally quaternized poly-4-vinyl pyridine and optionally quaternized poly(ethyleneimine), which can be prepared by polymerizing ethyleneimine and optionally quaternizing.
  • monomers comprising amine groups which are capable of being quaternized may be polymerized and then, optionally, converted to ammonium by a quaternization reaction, and/or may be quaternized prior to polymerization.
  • tertiary amine groups which are capable of being quaternized can be quaternized by reaction with a salt of the formula R'X wherein R' is a short chain alkyl, and X is an anion which forms a water soluble salt with the quaternized ammonium.
  • the at least one compound comprising at least two quaternary ammonium groups are cationic diallyl quaternary ammonium-comprising polymers such as dimethyldiallylammonium chloride homopolymer (CTFA designation: polyquaternium-6), copolymers derived from (i) acrylamide and (ii) dimethyldiallylammonium chloride (CTFA designation: polyquaternium-7); copolymers derived from (i) dimethyldiallylammonium chloride and (ii) sodium acrylate (CTFA designation: Polyquaternium-22); and terpolymers derived from (i) dimethyldiallylammonium chloride, (ii) acrylic amide and (iii) sodium acrylate (CTFA designation: Polyquatemium-39).
  • CTFA designation: polyquaternium-6 dimethyldiallylammonium chloride homopolymer
  • CTFA designation: polyquaternium-7 copolymers derived from (i) dimethyldiallylammonium chloride and
  • the at least one compound comprising at least two quaternary ammonium groups are derivatives of polysaccharide polymers such as cationic cellulose derivatives include cationic cellulose, which is available from Amerchol Corp. (Edison, N.J., USA) in their Polymer JRTM, LRTM and SRTM series of polymers as salts of hydroxyethyl cellulose reacted with trimethyl ammonium substituted epoxide (CTFA designation: polyquaternium-10), and polymeric quaternary ammonium salts of hydroxyethyl cellulose reacted with lauryl dimethyl ammonium-substituted epoxide (CTFA designation: polyquaternium-24), which is available under the tradename Polymer LM-200TM.
  • CTFA designation: polyquaternium-10 polymeric quaternary ammonium salts of hydroxyethyl cellulose reacted with lauryl dimethyl ammonium-substituted epoxide
  • cationic polysaccharides derivatives include cationic starch derivatives (such as quaternary starch, which is available from Croda); cationic guar gum derivatives (such as guar hydroxypropyltrimonium chloride, which is available from Celanese Corp. in their Jaguar R series); and quaternary nitrogen-containing cellulose ethers.
  • cationic starch derivatives such as quaternary starch, which is available from Croda
  • cationic guar gum derivatives such as guar hydroxypropyltrimonium chloride, which is available from Celanese Corp. in their Jaguar R series
  • quaternary nitrogen-containing cellulose ethers such as quaternary ammonium groups
  • silicone polymers comprising at least two quaternary ammonium groups.
  • the silicone polymers may be chosen from silicone polymers comprising at least two quaternary ammonium groups wherein the at least two quaternary ammonium groups may be terminal, pendant and/or form part of the polymeric skeleton.
  • silicone polymers are amodimethicone or trimethylsilylamodimethicone which are sold by Dow-Corning Corp. in the form of its aqueous cationic emulsion under the trade name Silicone Emulsion No.
  • the at least one compound comprising at least two quaternary ammonium groups is polyquaternium-10.
  • the at least one compound comprising at least two quaternary ammonium groups is polyquaternium-22, while in another embodiment, the at least one compound comprising at least two quaternary ammonium groups is polyethyleneimine. In yet another embodiment, the at least one compound comprising at least two quaternary ammonium groups is quaternized starch.
  • the at least one compound comprising at least two quaternary ammonium groups further comprises at least one counterion.
  • any anionic counterions may be used for the at least two quaternary ammonium groups.
  • counterions are halide ions, sulfate ions, and methylsulfate ions, acetate ions, tosylate ions and phosphate ions.
  • the at least one compound comprising at least two quaternary ammonium groups of the present invention may be present in an amount generally ranging from 0.01% to 10% of active material by weight relative to the total weight of the composition, such as from 0.1% to 0.5% of active material by weight.
  • the at least one compound according to the present invention may be commercially available, and may come from suppliers in the form of a dilute solution.
  • the amounts of the at least one compound comprising at least two quaternary ammonium groups disclosed herein therefore reflect the weight percent of active material.
  • the charge density of the at least one compound will be dependent on the pH and the isoelectric point of the at least two quaternary ammonium groups.
  • the C 3 to C 5 monosaccharides according to the present invention may be chosen from any triose, tetrose and pentose. (Nomenclature: C3 - triose, C4 - tetrose, C5 - pentose, C6 - hexose). Further, the C 3 to C 5 monosaccharides can be chosen from the D-form, L-form and mixtures of any of the foregoing.
  • Non- limiting examples of C 3 to C 5 monosaccharides include aldopentoses (such as xylose, arabinose, lyxose, and ribose), ketopentoses (such as ribulose and xylulose), aldotetroses (such as erythrose and treose), ketotetroses (such as erythrulose), aldotrioses (such as glyceraldehyde) and ketotrioses (such as dihydroxyacetone).
  • the C 3 to C 5 monosaccharides may be chosen from C 3 to C 5 monosaccharides comprising aldehyde groups (aldoses), furanoses and other ring structures.
  • the C 3 to C 5 monosaccharides may be substituted or unsubstituted.
  • Derivatives of C 3 to C 5 monosaccharides may be used as the at least one sugar of the present invention.
  • imine compounds are sometimes also referred to as Schiff bases.
  • Other non-limiting examples of derivatives of C 3 to C 5 monosaccharides are hemiacetal derivatives of C 3 to C 5 monosaccharides, hemiketal derivatives of C 3 to C 5 monosaccharides and any oxidized derivatives of C 3 to C 5 monosaccharides.
  • C 3 to C 5 monosaccharides may also include, but are not limited to, oligosaccharides derived from C 3 to C 5 monosaccharides, such as xylobiose.
  • the at least one sugar chosen from C 3 to C 5 monosaccharides may be substituted or unsubstituted.
  • the derivatives of C 3 to C 5 monosaccharides may be substituted or unsubstituted.
  • the at least one C to C 22 carbon chain may be chosen from linear, branched and cyclic C to C 22 carbon chains, which are saturated or unsaturated.
  • the at least one C., to C 22 carbon chain may optionally be substituted.
  • the at least one C ⁇ to C 22 carbon chain is chosen from C 16 to C 18 carbon chains.
  • the at least one C to C 22 carbon chain is chosen from C 16 carbon chains and C 18 carbon chains.
  • Non-limiting examples of C 16 carbon chains are linear hexadecyl chains, and non-limiting examples of C 18 carbon chains are linear octadecyl chains.
  • the at least one sugar may be substituted with the at least one C 1 to C 22 carbon chain at any position on the sugar.
  • the at least one sugar is substituted with at least one C, to C 22 carbon chain at the C1 position of the at least one sugar.
  • the at least one sugar is substituted with the at least one C, to C 22 carbon chain at at least one of the hydroxyl groups of the at least one sugar.
  • substituted at at least one of the hydroxyl groups of the at least one sugar means at least one of substitution on the hydroxyl group itself (i.e., formation of an ether linkage between the at least one sugar and the C, to C 22 carbon chain) and substitution on the carbon atom to which the hydroxyl group is commonly bonded.
  • the at least one sugar may be substituted with the at least one C, to C 22 carbon chain at a ring carbon atom bearing no hydroxyl groups (i.e., a CH 2 within the ring or a carbon atom within the ring bearing substituents other than a hydroxyl group).
  • the at least one C 5 to C 7 saccharide unit according to the present invention may be chosen from any pentose, hexose and heptose. Further, the at least one C 5 to C 7 saccharide unit can be chosen from their D-form, L-form and mixtures of any of the foregoing.
  • Non-limiting examples of C 5 to C 7 saccharide units are aldopentoses (such as xylose, arabinose, lyxose, and ribose), ketopentoses (such as ribulose and xylulose), aldohexoses (such as glucose and galactose), ketohexoses (such as fructose and sorbose), and heptoses (such as aldoheptoses and ketoheptoses, e.g., galactoheptulose and glucoheptulose).
  • the at least one C 5 to C 7 saccharide unit may be chosen from those comprising aldehyde groups (aldoses), furanoses and other ring structures.
  • the at least one C 5 to C 7 saccharide unit may be further substituted with at least one group different from the at least one amino group.
  • Derivatives of C 5 to C 7 saccharide units may also be used as the at least one C 5 to C 7 saccharide unit in the present invention.
  • imine compounds are sometimes also referred to as Schiff bases.
  • Other non-limiting examples of derivatives of C 5 to C 7 saccharide units are hemiacetal derivatives of C 5 to C 7 saccharide units, hemiketal derivatives of C 5 to C 7 saccharide units and any oxidized derivatives of C 5 to C 7 saccharide units.
  • These derivatives may be formed, for example, from the reaction of the aldehyde or ketone group of a saccharide unit with an alcohol.
  • the at least one C 5 to C 7 saccharide unit may be further substituted with at least one group different from the at least one amino group.
  • the derivatives of C 5 to C 7 saccharide units may be further substituted with at least one group different from the at least one amino group.
  • the at least one amino group may be chosen from substituted and unsubstituted amino groups.
  • the at least one amino group may be chosen from N-acetyl amino groups.
  • the at least one C 5 to C 7 saccharide unit may be substituted with the at least one amino group at any position on the saccharide unit.
  • the at least one C 5 to C 7 saccharide unit is substituted with the at least one amino group at the C1 position of the at least one C 5 to C 7 saccharide unit.
  • the at least one C 5 to C 7 saccharide unit is substituted with the at least one amino group at the C2 position of the at least one C 5 to C 7 saccharide unit.
  • Non-limiting examples of the at least one compound include C 5 monosaccharides substituted with at least one amino group, C 6 monosaccharides substituted with at least one amino group, C 7 monosaccharides substituted with at least one amino group, polymers comprising at least one C 5 monosaccharide substituted with at least one amino group, polymers comprising at least one C 6 monosaccharide substituted with at least one amino group, polymers comprising at least one C 7 monosaccharide substituted with at least one amino group, and glycoproteins comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group.
  • the at least one compound is chosen from oligosaccharides derived from the at least one C 5 to C 7 saccharide unit substituted with at least one amino group.
  • Non-limiting examples of C 5 monosaccharides substituted with at least one amino group are pentosamines.
  • the pentosamines are chosen from aldopentosamines and ketopentosamines (such as xylosamine, arabinosamine, lyxosamine, ribosamine, ribulosamine and xylulosamine).
  • Non-limiting examples of C 6 monosaccharides substituted with at least one amino group include hexosamines (such as aldohexosamines and ketohexosamines).
  • hexosamines are chosen from glucosamine, galactosamine, allosamine, altrosamine, mannosamine, gulosamine, idosamine, galactosamine, and talosamine.
  • the at least one compound is glucosamine, and in another embodiment, is galactosamine.
  • Non-limiting examples of C 7 monosaccharides substituted with at least one amino group are heptosamines.
  • heptosamines may be chosen from aldoheptosamines and ketoheptosamines.
  • the at least one sugar is present in the composition in an amount generally ranging from 0.01% to 10% by weight relative to the total weight of the composition, such as from 0.1% to 5% by weight.
  • compositions of the present invention as well as those of the inventive methods may further comprise at least one additional sugar which is different from the at least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C 5 monosaccharides substituted with at least one C 1 to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group.
  • the at least one additional sugar may, for example, aid in moisture retention.
  • the effectiveness of a sugar in aiding in moisture retention may be measured by monitoring a DSC peak at a temperature ranging from 75°C to 200°C.
  • the at least one additional sugar may be chosen from any sugar, carbohydrate or carbohydrate moiety.
  • Non-limiting examples of the at least one additional sugar are monosaccharides, which include, but are not limited to, three to seven carbon sugars such as pentoses (for example, ribose, arabinose, xylose, lyxose, ribulose, and xylulose) and hexoses (for example, allose, altrose, glucose, mannose, gulose, idose, galactose, talose, sorbose, psicose, fructose, and tagatose); oligosaccharides such as disaccharides (such as maltose, sucrose, cellobiose, trehalose and lactose); and polysaccharides such as starch, dextrins, cellulose and glycogen.
  • the at least one additional sugar is chosen from any aldoses and ketoses. Further, the at least
  • the at least one additional sugar may be substituted.
  • the at least one additional sugar may be substituted with at least one C, to C 22 carbon chain.
  • the at least one C to C 22 carbon chain is chosen from linear, branched and cyclic C ⁇ to C 22 carbon chains, which are saturated or unsaturated.
  • the at least one C 1 to C 22 carbon chain may be chosen from C 16 to C 18 carbon chains (such as C 1 ⁇ carbon chains and C 18 carbon chains).
  • C 16 carbon chains may be chosen from linear hexadecyl chains and C 18 carbon chains may be chosen from linear octadecyl chains.
  • the at least one additional sugar is substituted with at least one C to C 22 carbon chain at the C1 position of the at least additional one sugar.
  • the at least one additional sugar is present in the composition in an amount generally ranging from 0.01% to 10% by weight relative to the total weight of the composition, such as from 0.1% to 5% by weight.
  • compositions of the present invention as well as those used in the methods of the present invention may be in the form of a liquid, an oil, a paste, a stick, a dispersion, an emulsion, a lotion, a gel, or a cream.
  • inventive compositions may further comprise at least one solvent.
  • the at least one solvent include water and organic solvents.
  • a non-limiting example of organic solvents includes ethanol.
  • compositions may also comprise at least one suitable additive chosen from additives commonly used in compositions for keratinous fibers.
  • suitable additives include anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, fragrances, penetrating agents, antioxidants, sequestering agents, opacifying agents, solubilizing agents, emollients, colorants, screening agents (such as sunscreens and UV filters), preserving agents, proteins, vitamins, silicones, polymers such as thickening polymers, plant oils, mineral oils, synthetic oils and any other additive conventionally used in compositions for the care and/or treatment of keratinous fibers.
  • compositions of the present invention and those used in the methods of the present invention may also be provided as one-part compositions comprising at least one compound comprising at least two quaternary ammonium groups; at least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C 5 monosaccharides substituted with at least one C ⁇ to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group, and, optionally, at least one additional sugar, or in the form of a multi-component treatment or kit.
  • the skilled artisan based on the stability of the composition and the application envisaged, will be able to determine how the composition and/or multicomponent compositions should be stored and mixed.
  • simple sugars such as C 3 to C 5 monosaccharides are known to be stable at pH levels ranging from 4 to 9.
  • the sugars would be stored separately and added to the composition only at the time of application.
  • the present invention also relates to a kit for caring for, treating or durably conditioning at least one keratinous fiber comprising at least two compartments, wherein a first compartment comprises a first composition comprising at least one compound comprising at least two quaternary ammonium groups; and a second composition comprises a second composition comprising at least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C 5 monosaccharides substituted with at least one C, to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group.
  • At least one composition further comprises at least one additional sugar, different from the at least one sugar chosen from C 3 to C 5 monosaccharides, from C 3 to C 5 monosaccharides substituted with at least one C., to C 22 carbon chain and from one compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group.
  • the protocol used for the determination of the heat activated durable conditioning is as follows: bleached hair was treated with a solution containing at least one conditioning agent (0.4 g solution/hair) for 3 minutes then blotted dry. The treated hair was heated with a flat curling iron for 1 minute then shampooed six times with a 10% SLES solution (Sodium Lauryl Ether Sulphate). For the non-heated experiments, this step is omitted. Unless otherwise noted, all solutions comprised water as the solvent. The force needed to comb the wet hair was determined before the treatment, after the treatment and heat, and after the shampoo cycle. Each data point represents the average of a duplicate experiment.
  • polyquaternium-10 UCARE Polymer JR125 by AMERCHOL
  • sugar chosen from C 3 to C 5 monosaccharides i.e., xylose
  • Polyquaternium-10 in ethanol or a solution of 2% Polyquaternium-10 ( UCARE Polymer JR125 by AMERCHOL) and 1% xylose in ethanol. The hair was heated following the application of each solution. The results from the wet combability tests are shown in Table 2.
  • Example 3 The Effect of the Charge Density of the At Least One Compound Comprising At Least Two Quaternary Ammonium Groups Combined with Xylose
  • hair was treated with water, a solution containing a compound comprising at least two quaternary ammonium groups (i.e., quaternized starch), or a solution containing quaternized starch and at least one sugar chosen from C 3 to C 5 monosaccharides (i.e., xylose). Hair was treated with heat following the application of each solution.
  • quaternized starch a solution containing a compound comprising at least two quaternary ammonium groups
  • a solution containing quaternized starch and at least one sugar chosen from C 3 to C 5 monosaccharides i.e., xylose
  • Example 5 Heat Activated Effect of Polvethyleneimine Combined with Xylose Following the above protocol, hair was treated with a solution comprising polyethyleneimine (LUPASOL PL by BASF) or a solution comprising polyethyleneimine and at least one sugar chosen from C 3 to C 5 monosaccharides (i.e., xylose) and was heated following the application of each solution.
  • a solution comprising polyethyleneimine LPASOL PL by BASF
  • a solution comprising polyethyleneimine and at least one sugar chosen from C 3 to C 5 monosaccharides i.e., xylose
  • a negative Percent Increase indicates a better combability after treatment compared to non-treated hair.
  • Example 6 Heat Activated Durability of Polyquaternium-22 Following the above protocol, hair was treated with a solution comprising polyquaternium-22 (MERQUAT 280 by CALGON) or a solution comprising Polyquaternium-22 and xylose and, where indicated, was treated with heat following the application of the solution. The results from the wet combability tests are shown in Table 6. Table 6. Percent Increase in Wet Combing Force of Hair Treated with Polyquaternium-22.
  • Example 8 The Substantivitv of Polyguaternium-10 in the Heat Activated Conditioning
  • Example 10 The Concentration Effects of Polyquaternium-10 on the Heat Activated Durable Conditioning
  • the data showed that the conditioning effect was improved and more durable when the concentration of the at least one compound comprising at least two quaternary ammonium groups increased.
  • Bleached hair swatches were treated with a solution containing 6% Polyquaternium-22, then rinsed with warm water. A solution containing 1% xylose was then applied to the hair, which was blow-dried, then heated with a flat iron for 1 minute. The combability test was performed after the hair was shampooed 2, 4, and 6 times. Water was used instead of xylose as a control. The results from wet combability tests are shown in Table 12.
  • the protocol used for the determination of the heat activated durable conditioning is as follows: bleached hair was treated with a 80:20 alcohol to water solution containing 0.5% (0.4 g solution/hair) of polyquaternium-10 (UCARE Polymer JR-30M by AMERCHOL) and/or 0.5% Xyliance sold by SOLIANCE (a sugar chosen from C 3 to C 5 monosaccharides substituted with at least one C 1 to C 22 carbon chain ) for 3 minutes then blotted dry. The treated hair was heated with a flat curling iron for 1 minute then shampooed six times with a 10% SLES solution.
  • polyquaternium-10 UCARE Polymer JR-30M by AMERCHOL
  • SOLIANCE a sugar chosen from C 3 to C 5 monosaccharides substituted with at least one C 1 to C 22 carbon chain
  • the protocol used for the determination of the heat activated durable conditioning is as follows: bleached hair was treated with an aqueous solution containing 0.5% (0.4 g solution/hair) of polyquaternium-10 (UCARE Polymer JR- 30M by AMERCHOL) or 0.5% polyquaternium-10 (UCARE Polymer JR-30M by AMERCHOL) and 0.5% glucosamine hydrochloride (a compound comprising at least one C 5 to C 7 saccharide unit substituted with at least one amino group) for 3 minutes then blotted dry.
  • the treated hair was heated with a flat curling iron for 1 minute then shampooed six times with a 10% SLES solution.
  • Table 14 Percent Increase in Wet Combing Force of Hair Treated with Polyquaternium-10 or Polyquaternium-10 and Glucosamine Hydrochloride

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
EP02733135A 2001-03-30 2002-03-29 Wärmeaktivierte haarkonditionierungsmittel enthaltend saccharide und verwendung Withdrawn EP1377258A2 (de)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US821111 1992-01-15
US820858 1997-03-20
US09/820,858 US7459150B2 (en) 2001-03-30 2001-03-30 Heat activated durable conditioning compositions comprising an aminated C5 to C7 saccharide unit and methods for using same
US09/820,934 US20020172650A1 (en) 2001-03-30 2001-03-30 Heat activated durable conditioning compositions comprising C1 to C22 substituted C3 to C5 monosaccharides and methods for using same
US820934 2001-03-30
US09/821,111 US6486105B1 (en) 2001-03-30 2001-03-30 Heat activated durable conditioning compositions comprising C3 to C5 monosaccharides, and methods for using same
PCT/IB2002/002048 WO2002078655A2 (en) 2001-03-30 2002-03-29 Heat activated durable conditioning compositions comprising saccharides and methods for using the same

Publications (1)

Publication Number Publication Date
EP1377258A2 true EP1377258A2 (de) 2004-01-07

Family

ID=27420137

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02733135A Withdrawn EP1377258A2 (de) 2001-03-30 2002-03-29 Wärmeaktivierte haarkonditionierungsmittel enthaltend saccharide und verwendung

Country Status (3)

Country Link
EP (1) EP1377258A2 (de)
JP (1) JP2004525147A (de)
WO (1) WO2002078655A2 (de)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060257344A1 (en) * 2002-10-22 2006-11-16 L'oreal Heat activated durable styling compositions comprising saccharide type compounds and film forming agents
US7186277B2 (en) 2003-03-24 2007-03-06 L'oreal Sa Composition for dyeing keratin fibres, comprising a cationic para-phenylenediamine derivative substituted with a diazacyclohexane or diazacycloheptane ring
FR2854570B1 (fr) * 2003-05-09 2009-07-03 Oreal Procede de traitement des fibres keratiniques par application de chaleur
KR100906588B1 (ko) * 2005-04-20 2009-07-09 로레알 사카라이드형 화합물 및 필름형성제를 포함하는 가열활성화된 내구성있는 스타일링 조성물
JP4837543B2 (ja) * 2005-12-21 2011-12-14 ホーユー株式会社 染色された繊維の色調安定化方法
JP4837544B2 (ja) * 2005-12-21 2011-12-14 ホーユー株式会社 脱染後の染色処理又は脱色処理における染色性又は脱色性の低下抑制方法及び繊維処理剤組成物
WO2010051151A2 (en) * 2008-10-09 2010-05-06 Hercules Incorporated Cleansing formulations comprising non-cellulosic polysaccharides with mixed cationic substituents
JP5341628B2 (ja) * 2009-06-12 2013-11-13 ホーユー株式会社 毛髪処理剤組成物
WO2011074140A1 (en) * 2009-12-18 2011-06-23 L'oreal Process for treating keratin fibers
WO2011074143A1 (en) * 2009-12-18 2011-06-23 L'oreal Process for treating keratin fibers
WO2011074133A1 (en) * 2009-12-18 2011-06-23 L'oreal Process for treating keratin fibers
JP2013514265A (ja) * 2009-12-18 2013-04-25 ロレアル ケラチン繊維を処理する方法
GB2477534A (en) * 2010-02-05 2011-08-10 Ajit Lalvani Composition for the stimulation and regulation of the hair follicle
EP2857004B1 (de) 2013-10-07 2018-07-04 The Procter and Gamble Company Haarglättungsverfahren mit reduzierenden Zuckern
EP3082731B1 (de) 2013-12-19 2018-07-04 The Procter and Gamble Company Formung von keratinfasern unter verwendung eines wirkstoffs mit mindestens zwei funktionellen gruppen aus -c(oh)- und -c(= o)oh
CA2932628A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using a reducing composition and a fixing composition
EP3082736B1 (de) 2013-12-19 2018-08-08 The Procter and Gamble Company Formung keratinischer fasern mit 2-hydroxypropan-1,2,3-tricarboxyl- und/oder 1,2,3,4-butantetracarboxylsäure
JP6346951B2 (ja) 2013-12-19 2018-06-20 ザ プロクター アンド ギャンブル カンパニー ケラチン繊維の成形方法
US11129784B2 (en) 2013-12-19 2021-09-28 The Procter And Gamble Company Shaping keratin fibres using oxoethanoic acid and/or derivatives thereof
CN105828793B (zh) 2013-12-19 2019-06-18 宝洁公司 使用糖使角蛋白纤维成形
US9877559B2 (en) 2013-12-19 2018-01-30 The Procter & Gamble Comany Methods for shaping fibrous material and treatment compositions therefor
US9918921B2 (en) * 2013-12-19 2018-03-20 The Procter & Gamble Company Methods for shaping fibrous material and treatment compositions therefor
WO2015094837A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using carbonate ester
BR112017006555B1 (pt) * 2014-11-13 2020-12-01 Unilever Nv método para melhorar o volume de cabelo
US10034824B2 (en) 2014-11-13 2018-07-31 Conopco, Inc. Hair shaping composition
CN107106438A (zh) 2014-12-19 2017-08-29 宝洁公司 成形角蛋白纤维的方法
WO2016100257A1 (en) 2014-12-19 2016-06-23 The Procter & Gamble Company Shaping keratin fibres using arabinose and ethylene carbonate
EP3310325A1 (de) 2015-06-18 2018-04-25 The Procter and Gamble Company Formung von keratinfasern mit dialdehydverbindungen
EP3313364B1 (de) 2015-06-24 2019-10-23 Kao Germany GmbH Verfahren zur haarbehandlung
WO2016206740A1 (en) * 2015-06-24 2016-12-29 Kao Germany Gmbh Hair conditioning composition
EP3573493A1 (de) 2017-01-26 2019-12-04 Lubrizol Advanced Materials, Inc. Haarstylinggeräte und verfahren zum betrieb davon

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5612024A (en) * 1991-03-27 1997-03-18 Henkel Kommanditgesellschaft Auf Aktien Cosmetic preparations for the hair
EG20380A (en) * 1991-10-16 1999-02-28 Richardson Vicks Inc Enhanced skin penetration system for improved topical delivery of drugs
AU683014B2 (en) * 1992-08-24 1997-10-30 Msd Consumer Care, Inc. Apparatus and method for sunless tanning
DE59305092D1 (de) * 1992-09-29 1997-02-20 Henkel Kgaa Haarnachbehandlungsmittel
US5916543A (en) * 1996-12-18 1999-06-29 Schering-Plough Healthcare Products, Inc. Emulsions having minimal rub-in times
US20020098207A1 (en) * 1999-02-08 2002-07-25 Daniel H. Maes Cholesterol sulfate compositions for enhancement of stratum corneum function

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO02078655A3 *

Also Published As

Publication number Publication date
WO2002078655A2 (en) 2002-10-10
WO2002078655A3 (en) 2003-02-13
JP2004525147A (ja) 2004-08-19

Similar Documents

Publication Publication Date Title
US6486105B1 (en) Heat activated durable conditioning compositions comprising C3 to C5 monosaccharides, and methods for using same
WO2002078655A2 (en) Heat activated durable conditioning compositions comprising saccharides and methods for using the same
US8697143B2 (en) Heat activated durable styling compositions comprising saccharide type compounds and film forming agents
US7012048B2 (en) Composition and method for treating hair containing a cationic ampholytic polymer and an anionic benefit agent
US20020182163A1 (en) Heat activated durable styling compositions comprising C1 to C22 Substituted C3-C5 monosaccharides and methods for same
US7459150B2 (en) Heat activated durable conditioning compositions comprising an aminated C5 to C7 saccharide unit and methods for using same
EP3046535A1 (de) Verfahren zur semipermanenten haarglättung und nachpflege von haar
EP1814511A1 (de) Verfahren zur permanenten formung von haar mit einem kationischen zellulosederivat
US5612024A (en) Cosmetic preparations for the hair
WO2019193109A1 (en) Cosmetic composition comprising a polysaccharide, surfactants and fragments of one or more plants
EP0577636B2 (de) Haarkosmetische zubereitungen
KR20210136061A (ko) 데포지션 보조제로서 람노리피드
EP1402881A1 (de) Formulierung enthaltend mindestens ein Phosphate enthaltendes Silikone und mindestens ein Amin-Derivat, und Verwendung davon
US20020172650A1 (en) Heat activated durable conditioning compositions comprising C1 to C22 substituted C3 to C5 monosaccharides and methods for using same
US20030021758A1 (en) Heat activated durable styling compositions comprising C3-C5 monosaccharides and methods for same
EP1402878B1 (de) Zusammensetzungen mit mindestens einer Silikonkomponente und mindestens einem Amin, sowie Methoden zu deren Verwendung
US20040166126A1 (en) Heat activated durable styling compositions comprising aminated C5 to C7 saccharide unit and methods for same
JP2016098228A (ja) 毛髪にハリ・コシ、なめらかさ、すべり易さを付与する毛髪処理剤。
KR100906588B1 (ko) 사카라이드형 화합물 및 필름형성제를 포함하는 가열활성화된 내구성있는 스타일링 조성물
CN101496776B (zh) 含有糖类化合物和成膜剂的热活化耐久性定型组合物
DE102004056801A1 (de) Verdicktes Dauerverformungsmittel und Verfahren zur dauerhaften Verformung von Haaren
KR20080089678A (ko) 사카라이드형 화합물 및 필름형성제를 포함하는 가열 활성화된 내구성있는 스타일링 조성물
WO2022112961A1 (en) Cosmetic composition for the treatment of keratinic fibers and method comprising the application of said composition to the keratinic fibers
DE102005003748A1 (de) Verdicktes Dauerverformungsmittel und Verfahren zur dauerhaften Verformung von Haaren
MX2007006201A (en) Method for the permanent shaping of hair using a cationic cellulose derivative

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20031030

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO SI

17Q First examination report despatched

Effective date: 20060807

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20070220