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EP1492493A1 - Procede permettant de produire des effets de memoire de forme sur des cheveux - Google Patents

Procede permettant de produire des effets de memoire de forme sur des cheveux

Info

Publication number
EP1492493A1
EP1492493A1 EP03724997A EP03724997A EP1492493A1 EP 1492493 A1 EP1492493 A1 EP 1492493A1 EP 03724997 A EP03724997 A EP 03724997A EP 03724997 A EP03724997 A EP 03724997A EP 1492493 A1 EP1492493 A1 EP 1492493A1
Authority
EP
European Patent Office
Prior art keywords
hair
shape
shape memory
amino
poly
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Withdrawn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
EP03724997A
Other languages
German (de)
English (en)
Inventor
Andreas Lendlein
Werner Grasser
Karl Kratz
Thomas Krause
Axel Kalbfleisch
Günther LANG
Jürgen Allwohn
Johannes Burghaus
Gerhard Sendelbach
Detlef Mattinger
Stefan Uhl
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.)
MnemoScience GmbH
Original Assignee
MnemoScience GmbH
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 DE10215858A external-priority patent/DE10215858A1/de
Priority claimed from DE2002128120 external-priority patent/DE10228120B4/de
Application filed by MnemoScience GmbH filed Critical MnemoScience GmbH
Publication of EP1492493A1 publication Critical patent/EP1492493A1/fr
Withdrawn legal-status Critical Current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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/046—Aerosols; Foams
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—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)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/88—Polyamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers

Definitions

  • the present invention relates to a method for achieving a retrievable hair remodeling using active ingredients which impart a shape memory effect to the hair, in particular of macromers which can be crosslinked to shape memory polymers or of shape memory polymers.
  • Temporary hair shaping is usually carried out using compositions based on solutions or dispersions of hair-fixing polymers. Such products give the hair more or less hold, volume, elasticity, bounce and shine through the addition of polymer.
  • Styling products facilitate the shaping and creation of the hairstyle as a gel, improve the status of a hairstyle as a hairspray and increase the volume of the hair as a setting foam. It is disadvantageous that the desired effects are only of relatively short duration and are quickly lost again due to external influences such as combing, wind, high air humidity or contact with water.
  • Permanent hair shaping is usually done by permanent wave treatment. Here, disulfide bonds in the hair are reductively split, the hair is brought into the new shape and fixed by oxidative formation of new disulfide bonds. It is disadvantageous that the necessary chemical treatment of the hair with reducing and oxidizing agents cannot impair the structure of the hair.
  • JP 04-41416 discloses hair cosmetics which contain certain linear polyurethanes with a glass transition temperature Tg of 40-90 ° C.
  • Tg glass transition temperature
  • the object underlying the present invention was to provide a method and the products required for a retrievable, in particular for a repeatedly retrievable hair shaping with a high degree of restoration of a programmed hairstyle shape. Another object was to provide a method with which it is possible to achieve permanent hair styling without damaging the structure of the hair. Another task was to provide a method which makes it possible to easily undo temporary reshapings several times and to return to a previously created, programmed, permanent hairstyle shape with high accuracy. Another object was to provide a method which enables deformations of a hairstyle attributable to external influences to be reversed in a simple manner and with high accuracy and to return to a previously created, programmed, permanent hairstyle shape.
  • the object is achieved by a method for hair treatment, wherein - An active ingredient composition is applied to the hair, the active ingredient composition containing at least one active ingredient which is selected from substances which, alone or in combination with other substances, are capable of applying to the hair after application to the hair and after the treatment described below to give a shape memory effect; before, at the same time or after the application of the active substance composition, the hair is brought into a specific shape (permanent memory form) and the memory form is then fixed by inducing a chemical or physical change in the applied active substances; wherein after an intentional or unwanted deformation of the shape of the memory, the original shape of the memory can essentially be restored by physical stimulation.
  • a particular embodiment relates to a method for hair treatment, wherein - a composition which has at least one crosslinkable
  • Macromer which forms a shape memory polymer after crosslinking, is applied to the hair, the macromer containing a) crosslinkable regions that can be crosslinked by chemical bonds and b) thermoplastic regions that are not chemically crosslinkable, before, at the same time or subsequently, the hair is brought into a specific (permanent) shape and then the shape is fixed by chemical crosslinking of the macromer to form the shape memory polymer, the shape memory polymer having at least one transition temperature Ttrans.
  • Another object of the invention is a method for embossing a second hairstyle shape on a programmed, retrievable first hairstyle shape.
  • a hairstyle (permanent shape) programmed by the above-mentioned method is first heated to a temperature above Ttrans. The hair is then brought into the desired second (temporary) shape and the second shape is fixed by cooling to a temperature below Ttrans.
  • Another object of the invention is a method for
  • a hairstyle in a temporary shape or a hairstyle deformed by cold deformation is heated to a temperature above Ttrans.
  • Shape memory polymers in the sense of the invention are polymers from which materials can be produced with the property that they can be imprinted with any shape (permanent shape), into which they spontaneously and after deformation or after being imprinted with a second shape (temporary shape) convert back without external force by just warming up or by another energetic stimulus. Deformation and reconversion are possible several times. The degree to which the original, permanent form is achieved is generally somewhat lower in a first relaxation cycle, consisting of deformation and re-transformation, than in subsequent cycles, presumably because of the removal of defects, textures, etc. which are still present at the beginning. A particularly high degree of re-conversion becomes but then in the following
  • the degree of reconversion in the first relaxation cycle is preferably at least 30%, particularly preferably at least 50% and in the subsequent relaxation cycles preferably at least 60%, particularly preferred at least 80%. But it can also be 90% and more.
  • the degree of reconversion can be measured, as in the case of conventional curl retention measurements, by simply measuring the length of a treated lock of hair or by known, suitable tension-stretching experiments.
  • the shape memory effect of hair is the property that a certain hairstyle shape (permanent memory shape) after a deformation can be restored spontaneously and without external force by merely heating or by another energetic stimulus, i.e. preferably at least 30 in a first relaxation cycle %, particularly preferably at least 50% and in the subsequent relaxation cycles preferably at least 60%, particularly preferably at least 80% or 90%.
  • Macromers or prepolymers which can be crosslinked to form shape memory polymers in the context of the invention are polymers or oligomers in which an impressed permanent shape is fixed in that individual polymer or oligomer strands are linked to one another by chemical bonds.
  • Crosslinking via chemical bonds can take place via ionic or covalent bonds.
  • the crosslinking reaction can be any chemical reaction, e.g. a salt formation reaction, a condensation reaction, an addition reaction, a substitution reaction or a radical or photochemically induced reaction.
  • the crosslinking reaction can be carried out using suitable catalysts or initiators or without a catalyst. It can be triggered by a suitable energy source, e.g. through electromagnetic radiation, ultrasound, heat or mechanical energy.
  • a combination of two or more starting methods can optionally be used to increase the efficiency or the speed of the crosslinking reaction.
  • Shape memory polymers suitable according to the invention have at least one transition temperature Ttrans.
  • This can be a Melting temperature T m or a glass transition temperature Tg.
  • T trans the polymer has a lower modulus of elasticity than below Ttrans- Since s lower ratio of the elasticity modules and Ttrans i above st preferably at least 20.
  • the transition temperature Ttrans st preferably greater than room temperature (20 ° C), especially at least 30 ° C, particularly preferably at least 40 ° C and is the temperature above which the spontaneous regression of the permanent form from the de-deformed or from the temporary form takes place.
  • Hairstyle or hairstyle form in the sense of the invention is to be understood broadly and includes, for example, the degree of curl or the degree of smoothness of hair.
  • a programmed hairstyle in the sense of the invention is a collection of hair that is networked and fixed in a permanent form
  • Shape memory polymers have a certain shape.
  • Restoring a programmed hairstyle in the sense of the invention means that after a deformation the programmed hairstyle regresses again preferably at least 60%, particularly preferably at least 80%, based on the shape that arises after a first relaxation cycle.
  • the degree of restoration can take place, for example, by measuring the length of a lock of hair or a strand of hair.
  • Macromers or prepolymers are macromonomers that can be polymerized or cross-linked by individual chemical bonds.
  • the chemically crosslinked polymers are also referred to in WO 99/42147 as thermoset polymers.
  • the macromers and thermoset polymers described in WO 99/42147 are suitable according to the invention and form part of this application.
  • Soft, thermoplastic segments (switching segments) with a transition temperature Ttrans are cross-linked by chemical, preferably covalent bonds. So there are switching segments and Network points are required, with the network points fixing the permanent shape and the switching segments the temporary shape.
  • the shape memory effect is based on the change in elasticity when the Ttrans exceeds or falls below.
  • the ratio of the elasticity modules below and above Ttrans is preferably at least 20.
  • thermoset polymers with shape memory properties there are four types of thermoset polymers with shape memory properties: network polymers, penetrating networks, semi-penetrating networks and mixed-penetrating networks.
  • Network polymers can be formed by covalently linking macromonomers, ie oligomers or polymers with linkable, reactive end groups, preferably ethylenically unsaturated, radical or photochemically reactive end groups.
  • the crosslinking reaction can be started, for example, by light- or heat-sensitive initiators, by redox systems or their combinations or without initiators, for example by UV light, heat or mechanical energy input.
  • Pervasive networks are formed from at least two components, each of which is not networked with each other.
  • Mixed penetrating networks are formed from at least two components, one component being cross-linked by chemical bonds and another component by physical interactions.
  • Semi-penetrating networks are formed from at least two components, one of which is chemically crosslinkable and the other is not crosslinkable and both components cannot be separated by physical methods.
  • Suitable macromers are, for example, those of the general formula Al- (X) n -A2 (I) where AI and A2 are reactive, chemically crosslinkable groups and - (X) n- is a divalent, thermoplastic polymer or oligomer segment. AI and A2 are preferably acrylate or methacrylate groups.
  • the segment (X) n preferably represents polyester, oligoester, polyalkylene glycol, oligoalkylene glycol, polyalkylene carbonate and oligoalkylene carbonate segments, the alkylene groups preferably being ethylene or propylene groups.
  • Suitable macromonomers for the formation of thermoset polymers with shape memory properties are oligo- or poly ( ⁇ -caprolactones), oligo- or polylactides, oligo- or polyalkylene glycols, for example
  • Polyethylene or polypropylene glycol or their block copolymers the polymers or oligomers mentioned being substituted in the end or laterally with at least two free-radically polymerizable, ethylenically unsaturated groups, for example acrylates or methacrylates.
  • the polymer segments can be segments derived from natural polymers such as proteins or polysaccharides. They can also be synthetic polymer blocks. Suitable natural polymer segments are proteins such as zein, modified zein, casein, gelatin, gluten, serum albumin or collagen, and also polysaccharides such as alginates, celluloses, dextran, pullulan or polyhyaluronic acid as well as chitin, poly (3-hydroxyalkanoate), in particular poly (ß-hydroxybutyrate) ), Poly (3-hydroxyoctanoate) or poly (3-hydroxy fatty acids). Derivatives of natural polymer segments, for example alkylated, hydroxyalkylated, hydroxylated or oxidized modifications, are also suitable.
  • Synthetically modified natural polymers are, for example, cellulose derivatives such as alkyl celluloses, hydroxyalkyl celluloses, cellulose loose ethers, cellulose esters, nitrocelluloses, chitosan or chitosan derivatives, which are obtained for example by N- or / and O-alkyl or hydroxyalkyl substitution.
  • cellulose derivatives such as alkyl celluloses, hydroxyalkyl celluloses, cellulose loose ethers, cellulose esters, nitrocelluloses, chitosan or chitosan derivatives, which are obtained for example by N- or / and O-alkyl or hydroxyalkyl substitution.
  • Examples are methyl cellulose, ethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose, hydroxybutyl methyl cellulose, cellulose acetate, cellulose propionate, cellulose acetate butyrate, cellulose acetate phthalate, carboxymethyl cellulose, cellulose tri
  • Suitable synthetic polymer blocks are polyphosphazenes, poly (vinyl alcohols), polyamides, polyester amides, polyamino acids, polyanhydrides, polycarbonates, poly (lactide-co-glycolides), polyacrylates, polyalkylenes, polyacrylamides, polyalkylene glycols, polyalkylene oxides, polyalkylene terephthalates, polyorthoesters, polyvinyl ethers, polyvinyl halides, polyvinyl halides , Polyvinylpyrrolidone, polyester, polylactide, polyglycolide, polysiloxane, polyurethane and their copolymers.
  • suitable polyacrylates are poly (methyl methacrylate), poly (ethyl methacrylate), poly (butyl methacrylate),
  • Suitable synthetic, easily biodegradable polymer segments are polyhydroxy acids such as polylactides, polyglycolides and their copolymers, poly (ethylene terephthalate), - poly (hydroxybutanoic acid), - poly (hydroxyvaleric acid); Poly [lactide-co- ( ⁇ -caprolactone)]; Poly [glycolide-co- ( ⁇ -caprolactone)]; Polycarbonates, poly (amino acids); Poly (hydroxyalkanoates), polyanhydrides; Polyorthoesters and their mixtures and copolymers.
  • poorly biodegradable polymer segments are poly (methacrylic acid), poly (acrylic acid), polyamides, polyethylene, polypropylene, polystyrene, Polyvinyl chloride, polyvinylphenol and their mixtures and copolymers.
  • the composition contains a mixture of (A) macromers which are substituted with at least two reactive, crosslinkable groups and (B) macromers which are substituted with only one reactive group.
  • Suitable additional macromers are, for example, those of the general formula R- (X ') n -A3 (II) where R for a monovalent organic radical, A3 for a reactive, chemically crosslinkable group and - (X') n- for a divalent, thermoplastic Polymer or oligomer segment stands.
  • A3 is preferably an acrylate or methacrylate group.
  • the segment (X ') n preferably stands for polyalkylene glycols, their monoalkyl ethers and their block copolymers, the alkylene groups preferably being ethylene or propylene groups and the alkyl groups preferably having 1 to 30 C atoms.
  • Mixtures of (A) are particularly preferably esterified at both ends with acrylic or methacrylic acid
  • component (A) poly ( ⁇ -caprolactone) dimethacrylate, poly (DL-lactide) dimethacrylate, poly (L-lactide-co-glycolide) dimethacrylate, poly (ethylene glycol) dimethacrylate, poly (propylene) glycol) dimethacrylate, PEG-block-PPG-block-PEG-dimethacrylate, poly (ethylene adipate) dimethacrylate, hexamethylene carbonate dimethacrylate.
  • component (B) are, for example: poly (ethylene glycol) monoacrylate, poly (propylene glycol) monoacrylate and their monoalkyl ether. Another special embodiment relates to a method for
  • composition which contains at least one shape memory polymer is applied to the hair, the shape memory polymer having at least two transition temperatures
  • Ttrans un & ⁇ 'trans and a) at least one hard segment which can be crosslinked by physical interaction with a first transition temperature T'trans »which is above room temperature, preferably more than 10 ° C. above room temperature, and b) at least one soft segment with a second transition temperature T'trans »which is above room temperature, preferably more than 10 ° C. above room temperature, and b) at least one soft segment with a second transition temperature T'trans »which is above room temperature, preferably more than 10 ° C. above room temperature, and b) at least one soft segment with a second
  • Transition temperature T rans » which is below T'trans», preferably at least 10 ° C below T'trans, has - before, at the same time or subsequently, the hair is brought into a specific (permanent) shape and then the shape by physical crosslinking the shape memory polymer is fixed.
  • the hair is expediently shaped with heating to a temperature of at least T'trans and the hair shape is fixed by cooling to a temperature below T'trans.
  • Room temperature usually means ambient temperature, preferably at least 20 ° C, in warmer climates preferably at least 25 ° C.
  • the composition can be applied to the hair in various ways, for example directly
  • composition can be, for example, that of a solution, dispersion, lotion, thickened lotion, gel, foam, a semi-solid mass, creamy or waxy.
  • Another object of the invention is a method for embossing a second hairstyle shape on a programmed, retrievable first hairstyle shape.
  • a hairstyle (permanent shape) programmed by the above-mentioned method is first heated to a temperature between T'trans un ( 3 Ttrans). The hair is then brought into the desired second (temporary) shape and the second shape is cooled to a Fixed temperature below Ttrans.
  • Another object of the invention is a method for restoring a first hairstyle (permanent shape) previously programmed by the above-mentioned method.
  • a hairstyle in a temporary shape or a hairstyle deformed by cold deformation is heated to a temperature above Ttrans.
  • the permanent form regresses spontaneously and automatically.
  • Cold shaping of a hairstyle means a hairstyle change at ambient temperature without the addition of additional heat by a hair dryer or similar devices.
  • the deformation can be caused mechanically, e.g. by simply unhooking the curls under the influence of gravity, by combing or brushing the hair, by wind or moisture, by mechanical influences while sleeping or lying down etc.
  • the invention also relates to a method for reprogramming a permanent hairstyle shape previously programmed according to the above-mentioned method into another, new permanent shape.
  • the original hairstyle is heated to a temperature above T'trans and the hair is brought into a new shape.
  • the new shape is then fixed by cooling to a temperature below T'trans.
  • physically crosslinkable shape memory polymers are polymers in which the impressed permanent shape is fixed by crosslinking on the basis of physical interactions.
  • Networking through physical Interactions can take place in that certain segments of the polymer chains assemble into crystalline areas.
  • the physical interactions can be charge transfer complexes, hydrogen bonds, dipolar or hydrophobic interactions, van der Waals interactions or ionic interactions of polyelectrolyte segments.
  • the interactions can take place between different segments within a polymer strand (intramolecular) and / or between different polymer strands (intermolecular).
  • the formation of the interactions can be triggered, for example, by cooling (in particular in the case of crystallizations) and / or by drying, ie by removing solvents.
  • Physically crosslinkable shape memory polymers suitable according to the invention have at least two transition temperatures Ttrans and d T'trans. Both transition temperatures can be, for example, melting temperatures T m or glass transition temperatures Tg. Above T trans, the polymer has a lower modulus of elasticity than below Ttrans • lower the ratio of the elasticity modules and Ttrans above st preferably at least 10, more preferably at least 20.
  • the lower transition temperature Ttrans i st preferably greater than room temperature (20 ° C) , in particular at least 30 ° C., particularly preferably at least 35 ° C. or at least 40 ° C., and is the temperature above which the spontaneous regression of the permanent shape from the deformed or from the temporary shape occurs.
  • Ttrans is preferably so far above the usual ambient temperatures that no significant, unintended, thermally induced deformation of the temporary hairstyle shape occurs at ambient temperature. Suitable ranges for Ttrans are, for example, from 25 to 100 ° C, from 30 to 75 ° C, from 35 to 70 ° C or from 40 to 60 ° C.
  • the upper transition temperature T'trans is via Ttrans and is the temperature above which the permanent shape is embossed or the permanent shape is embossed into a new permanent shape and below which the permanent shape is fixed.
  • T'trans is preferably so far above Ttrans that when the hairstyle is heated to a temperature above Ttrans to restore the permanent hairstyle shape or to create a temporary hairstyle shape while maintaining the permanent hairstyle shape, no significant, unintentional, thermally induced deformation of the permanent hairstyle shape occurs.
  • T'trans is preferably at least 10 ° C, particularly preferably at least 20 ° C or at least 30 ° C above Ttrans-D difference between T'trans and Ttrans can be, for example, from 10 to 80 ° C, from 20 to 70 ° C or from 30 to 60 ° C. Suitable ranges for T'trans are, for example, from 40 to 150 ° C, from 50 to 100 ° C or from 70 to 95 ° C.
  • Suitable physically cross-linked shape memory polymers are polymers which consist of at least one hard segment and at least one soft segment.
  • the hard segment has physical cross-links and has a transition temperature T'trans ° Lie above room temperature, preferably more than 10 ° C above 20 ° C.
  • the soft segment has a transition temperature Ttra s »which is below T'trans», preferably at least 10 ° C. below T'trans.
  • the polymer segments are preferably oligomers, in particular linear chain molecules with a molecular weight of, for example, 400 to 30,000, preferably 1000 to 20,000 or 1,500 to 15,000. They can be linear di, tri, tetra or multiblock copolymers, branched, dendritic or grafted copolymers ,
  • thermoplastic polymers are preferably not linear polyether urethanes which contain bis (2-hydroxyethyl) hydroquinone.
  • the molecular weight of the polymers can be, for example, from 30,000 to 1,000,000, preferably from 50,000 to 700,000 or from 70,000 to 400,000.
  • Suitable physically cross-linked shape memory polymers are described in WO 99/42147 and are referred to there as thermoplastic polymers.
  • the thermoplastic polymers described in WO 99/42147 and the production methods described therein are suitable according to the invention and form part of this application. You assign one
  • the polymer segments can be natural polymers such as e.g. Proteins or polysaccharide derived segments act. They can also be synthetic polymer blocks. Suitable natural or synthetic polymer segments are the same as those mentioned above for the crosslinkable macromers.
  • Suitable shape memory polymers are in particular multiblock copolymers which have at least one first type of blocks and at least one different second type of blocks, the blocks causing the multiblock copolymer to have two different transition temperatures.
  • Suitable multiblock copolymers are, in particular, those which are produced from at least two different macrodiols and at least one diisocyanate.
  • Macrodiols are oligomers or polymers with at least two free hydroxy groups. Oligomers generally consist of at least two, preferably at least three, in particular 4 to 20, 5 to 15 or 6 to 10 monomers.
  • the macrodiols can have the general formula HO-A-OH, where A is a divalent, oligomeric or polymeric group, preferably polyester or oligoester.
  • the diisocyanate can have the general formula OCN-B-NCO, where B is a divalent organic group, preferably an alkylene or arylene group, which can be substituted by further substituents.
  • B is a divalent organic group, preferably an alkylene or arylene group, which can be substituted by further substituents.
  • the alkylene group can be linear, branched or cyclic and preferably has 1 to 30 C atoms, particularly preferably 2 to 20 or 5 to 15 C atoms.
  • Particularly preferred shape memory polymers are the copolyester urethanes described in WO 99/42147, in particular the reaction products from (a) two different macrodiols, selected from ⁇ , ⁇ -dihydroxy-polyesters, ⁇ , ⁇ -dihydroxy-oligoesters, ⁇ , ⁇ -dihydroxy-polylactones and ⁇ , ⁇ -dihydroxy-oligolactones and (b) at least one diisocyanate, preferably trimethylhexane-1,6-diisocyanate.
  • two different macrodiols selected from ⁇ , ⁇ -dihydroxy-polyesters, ⁇ , ⁇ -dihydroxy-oligoesters, ⁇ , ⁇ -dihydroxy-polylactones and ⁇ , ⁇ -dihydroxy-oligolactones
  • at least one diisocyanate preferably trimethylhexane-1,6-diisocyanate.
  • Macrodiols made from poly (para-dioxanone) (PDX), poly (pentadecalactone) (PDL), poly ( ⁇ -caprolactone) (PCL), poly (L-lactide-co-glycolide) (PLGA).
  • the molecular weights of the macrodiols are preferably in the range from 400 to 30,000, preferably 1,000 to 20,000 or 1,500 to 15,000.
  • the polydispersities are preferably in the range from 1.7 to 2.0.
  • a further particular embodiment relates to a method for hair treatment using an active ingredient composition which contains at least two active ingredients which individually have no or only weak shape memory properties and which, when used together in accordance with the abovementioned methods, give hair a synergistically increased shape memory effect.
  • compositions according to the invention for hair treatment contain at least one active ingredient which brings about a shape memory effect on hair in an amount of preferably from 0.01 to 25% by weight, particularly preferably from 0.1 to 15% by weight, in a suitable medium.
  • the composition can be in the form of a solution, dispersion, emulsion, suspension or latex.
  • the liquid, gel-like, semi-solid or solid medium is essentially cosmetically acceptable and physiologically harmless.
  • composition according to the invention is generally in the form of a solution or dispersion in a suitable solvent.
  • Aqueous, alcoholic or aqueous-alcoholic solvents are particularly preferred.
  • Suitable solvents are e.g. aliphatic Cl to C4 alcohols or a mixture of water with one of these alcohols.
  • other organic solvents can also be used, in particular unbranched or branched hydrocarbons such as pentane, hexane, isopentane, cyclic hydrocarbons such as cyclopentane and cyclohexane, organic linear or cyclic ethers, e.g. Tetrahydrofuran (THF) or liquid organic esters, e.g. Ethyl acetate should be mentioned.
  • THF Tetrahydrofuran
  • silicone-based solvents are also suitable, in particular silicone oils based on linear or cyclic polydimethylsiloxanes (dimethicone or cyclomethicone).
  • the solvents are preferably present in an amount of 0.5 to 99% by weight, particularly preferably in an amount of 40 to 90% by weight.
  • compositions according to the invention can additionally contain 0.01 to 25% by weight of at least one hair-care, hair-fixing and / or hair-coloring active ingredient.
  • Hair-setting active ingredients are in particular the known, conventional film-forming and hair-fixing polymers.
  • the film-forming and hair-fixing polymer can be of synthetic or natural origin and have nonionic, cationic, anionic or amphoteric character.
  • Such a polymer additive which can be contained in amounts of 0.01 to 25% by weight, preferably 0.1 to 20% by weight, particularly preferably 0.5 to 15% by weight, can also be made from a mixture of several polymers exist and by the addition of other polymers with thickening effect in its hair-setting properties be modified.
  • film-forming, hair-fixing polymers are understood to mean those polymers which, when used in 0.01 to 5% aqueous, alcoholic or aqueous-alcoholic solution, are able to deposit a polymer film on the hair and in this way to strengthen the hair.
  • Suitable synthetic, nonionic, film-forming, hair-fixing polymers in the hair treatment composition according to the invention are homopolymers of vinylpyrrolidone, homopolymers of N-vinylformamide, copolymers of vinylpyrrolidone and vinyl acetate, terpolymers of vinylpyrrolidone, vinyl acetate and vinyl propionate, polyacrylamides, or polyethyleneglycols, polyvinyl alcohols up to 20,000 g / mol can be used.
  • Suitable synthetic, film-forming anionic polymers should be mentioned
  • Amphoteric polymers can also be used in the hair treatment composition according to the invention. Are suitable for. B.
  • copolymers of octylacrylamide, t-butylaminoethyl methacrylate and two or more monomers from the group consisting of acrylic acid, methacrylic acid and their simple esters are particularly useful as copolymers of vinyl pyrrolidone with quaternized derivatives of dialkylaminoacrylate and methacrylate, such as vinylpyrrolidone / dimethylaminomethacrylate copolymers quaternized with diethyl sulfate.
  • cationic polymers include the copolymer of vinyl pyrrolidone with vinyl, the terpolymer of dimethyldiallyl ammonium chloride, sodium acrylate and acrylamide, the terpolymer of vinylpyrrolidone, dimethylaminoethyl methacrylate and Vinylcarprolactam, the quaternized ammonium salt prepared from hydroxyethyl cellulose and a trimethylammonium-substituted epoxide, vinyl pyrrolidone / Methacrylamidopropyltrimethylammonium chloride copolymer and diquaternary polydimethylsiloxanes.
  • the consistency of the hair treatment composition according to the invention can be increased by adding thickeners.
  • a cosmetic agent according to the invention can be used in various application forms, for example in the form of a lotion, a spray lotion, a cream, a gel, a gel foam, an aerosol spray, a non-aerosol spray, an aerosol foam, a non-aerosol foam, an O / W or W / 0- emulsion, a microemulsion or a hair wax.
  • the hair treatment composition according to the invention is in the form of an aerosol spray, it additionally contains 15 to 85% by weight, preferably 25 to 75% by weight, of a propellant and is filled in a pressure container with a spray head.
  • Lower alkanes such as, for example, n-butane, isobutane and propane, or else mixtures thereof, and also dimethyl ether or fluorocarbons are used as blowing agents such as F 152a (1, 1-difluoroethane) or F 134 (tetrafluoroethane) and, furthermore, gaseous blowing agents such as N 2 , N2O and C0 2 and mixtures of the abovementioned blowing agents are suitable at the pressures under consideration.
  • the hair treatment composition according to the invention is in the form of a sprayable non-aerosol hairspray, it is sprayed with the aid of a suitable mechanically operated spraying device.
  • Mechanical spraying devices are to be understood as devices which spray one
  • a suitable mechanical spray device can be, for example, a spray pump or an elastic container provided with a spray valve, in which the cosmetic agent according to the invention is filled under pressure, the elastic one
  • the hair treatment composition according to the invention is in the form of a hair foam (mousse), then it contains at least one customary, known foaming substance.
  • the agent is foamed with or without the help of propellant gases or chemical propellants and incorporated into the hair as a foam and left in the hair without rinsing.
  • a product according to the invention has a device for foaming the composition as an additional component.
  • Devices for foaming are to be understood as devices which allow the foaming of a liquid with or without the use of a blowing agent.
  • a commercially available pump foamer or an aerosol foam head can be used, for example, as a suitable mechanical foaming device.
  • the hair treatment composition according to the invention is in the form of a hair gel, it additionally contains at least one gel-forming substance in an amount of preferably 0.05 to 10, particularly preferably 0.1 to 2% by weight.
  • the viscosity of the gel is preferably from 100 to 50,000 mm / s, particularly preferably from 1,000 to 15,000 mm / s at 25 ° C., measured as a dynamic viscosity measurement using a Bohlin Rheometer CS, measuring body C25 at a shear rate of 50 s.
  • Hair wax is present, it additionally contains water-insoluble fat or wax substances or substances which give the composition a wax-like consistency in an amount of preferably 0.5 to 30% by weight.
  • Suitable water-insoluble substances are, for example, emulsifiers with an HLB value below 7, silicone oils, silicone waxes, waxes (for example wax alcohols, wax acids, wax esters, and in particular natural waxes such as beeswax, carnauba wax, etc.), fatty alcohols, fatty acids, fatty acid esters or high molecular weight polyethylene glycols a molecular weight of 800 to 20,000, preferably from 2,000 to 10,000 g / mol.
  • the hair treatment composition according to the invention is in the form of a hair lotion, it is in the form of an essentially non-viscous or slightly viscous, flowable solution, dispersion or emulsion containing at least 10% by weight, preferably 20 to 95% by weight, of a cosmetically acceptable alcohol in front.
  • a cosmetically acceptable alcohol in front.
  • the lower C1 to C4 alcohols commonly used for cosmetic purposes such as e.g. Ethanol and isopropanol can be used.
  • the hair treatment composition according to the invention is in the form of a hair cream, it is preferably in the form of an emulsion and either additionally contains viscosity-imparting ingredients a quantity of 0.1 to 10% by weight or the required viscosity and creamy consistency is built up in a conventional manner by micelle formation with the aid of suitable emulsifiers, fatty acids, fatty alcohols, waxes etc.
  • the agent according to the invention is capable of simultaneously embossing a retrievable hairstyle as well as hair coloring.
  • the agent is then used as a coloring hair treatment agent, e.g. Formulated as a color fixer, coloring cream, coloring foam etc. It then contains at least one coloring substance.
  • These can be organic dyes, in particular so-called direct dyes, or inorganic pigments.
  • the total amount of dyes in the composition according to the invention is about 0.01 to 7% by weight, preferably about 0.2 to 4% by weight.
  • Direct dyes suitable for the agent according to the invention are, for example, triphenylmethane dyes, aromatic nitro dyes, azo dyes, quinone dyes, cationic or anionic dyes. Suitable are: Nitro dyes (blue):
  • Nitro dyes (red): l-amino-4- [(2-hydroxyethyl) amino] -2-nitrobenzene (HC Red No. 7), 2-amino-4, 6-dinitro-phenol, 1, 4-diamino-2 -nitrobenzene (CI76070), 4-amino-2-nitro-diphenylamine (HC Red No. 1), l-amino-4- [di (2-hydroxyethyl) amino] -2-nitrobenzene hydrochloride (HC Red No. 13 ), 1-Amino-5-chloro-4- [(2-hydroxyethyl) amino] -2-nitrobenzene, 4-amino-l- [(2-hydroxyethyl) amino] -2-nitrobenzene (HC Red No.
  • Nitro dyes (yellow): 1,2-diamino-4-nitrobenzene (CI76020), 1,2-amino-2- [(2-hydroxyethyl) amino] -5-nitrobenzene (HC Yellow No. 5), 1- (2-hydroxyethoxy) -2 - [(2-hydroxyethyl) amino] -5-nitrobenzene (HC Yellow No. 4), l - [(2-hydroxyethyl) amino] -2-nitrobenzene (HC Yellow No.
  • Basic dyes 9- (dimethylamino) benzo [a] phenoxazin-7-ium chloride (CI51175; Basic Blue No. 6), di [4- (diethylamino) phenyl] [4- (ethylamino) naphthyl] carbenium -chloride (CI42595; Basic Blue No. 7), di- (4- (dimethylamino) phenyl) - (4- (methyl-phenylamino) naphthalene-l-yl) - carbenium chloride (CI42563; Basic Blue No. 8) , 3,7-Di (dimethylamino) phenothiazine-5-ium chloride (CI52015 Basic Blue No.
  • Acid dyes 6-hydroxy-5- [(4-sulfophenyl) azo] -2-naphthalenesulfonic acid disodium salt (CI15985; Food Yellow No. 3; FD&C Yellow No. 6), 2, 4-dinitro-l-naphthol-7 -sulfonic acid disodium salt (CI10316; Acid Yellow No. 1; Food Yellow No. 1), 2- (indan-1, 3-dion-2-yl) quinoline- x, x-sulfonic acid (mixture of mono- and disulfonic acid) (CI47005; D&C Yellow No. 10; Food Yellow No. 13; Acid Yellow No.
  • Suitable hair-coloring pigments are colorants which are practically insoluble in the application medium and can be inorganic or organic. Inorganic-organic mixed pigments are also possible. Both
  • Pigments are preferably not nanopigments.
  • the preferred particle size is 1 to 200 ⁇ m, in particular 3 to 150 ⁇ m, particularly preferably 10 to 100 ⁇ m.
  • Inorganic pigments are preferred.
  • the inorganic pigments can be of natural origin, for example made from chalk, ocher, U bra, green earth, burnt terra di Siena or graphite.
  • the pigments can be white pigments such as titanium dioxide or zinc oxide, black pigments such as iron oxide black, colored pigments such as ultramarine or Iron oxide red, around luster pigments, metallic effect pigments, pearlescent pigments as well as around fluorescent or
  • Act phosphorescent pigments preferably at least one pigment being a colored, non-white pigment.
  • Metal oxides, hydroxides and oxide hydrates, mixed phase pigments, sulfur-containing silicates, metal sulfides, complex metal cyanides, metal sulfates, chromates and molybdates as well as the metals themselves (bronze pigments) are suitable.
  • Titanium dioxide (CI 77891), black iron oxide (CI 77499), yellow iron oxide (CI 77492), red and brown iron oxide (CI 77491), manganese violet (CI 77742), ultramarine (sodium aluminum sulfosilicate, CI 77007, pigment blue 29 ), Chromium Oxide Hydrate (CI77289), Iron Blue (Ferric Ferrocyanide, CI77510), Carmine (Cochineal).
  • Pigments based on mica or mica are particularly preferred, which are coated with a metal oxide or a metal oxychloride such as titanium dioxide or bismuth oxychloride and optionally other colorants such as iron oxides, iron blue, ultramarine, carmine, etc., and the color is determined by varying the layer thickness.
  • Pigments of this type are sold, for example, under the trade names Rona, Colorona, Dichrona and Timiron by Merck, Germany.
  • Organic pigments are e.g. the natural pigments sepia, gum, bone char, Kasseler brown, indigo, chlorophyll and other plant pigments.
  • Synthetic organic pigments are e.g. Azo pigments, anthraquinones, indigoids,
  • the hair treatment composition according to the invention preferably additionally contains at least one hair-care substance in an amount of 0.01 to 10, particularly preferably 0.05 to 5% by weight.
  • Preferred hair care substances are silicone compounds and cationic substances which are based on cationic or cationizable groups, especially primary, secondary, tertiary or quaternary amine groups have a substantivity to human hair.
  • Suitable cationic substances are selected from cationic surfactants, betaine, amphoteric surfactants, cationic polymers, silicone compounds with cationic or cationizable groups, cationically derivatized proteins or protein hydrolyzates and betaine.
  • Suitable silicone compounds are e.g. Polydimethylsiloxane (INCI: Dimethicone), ⁇ -Hydro- ⁇ -hydroxypolyoxydimethylsilylene (INCI: Dimethiconol), cyclic Dimethylpolysiloxan (INCI: Cyclomethicone), Trimethyl (octadecyloxy) silane (INCI: Stearoxy-trimethylsilane), DimethylsiloxyI / Dimethylethiliconol / INC ), dimethylsiloxane / aminoalkylsiloxane copolymer having hydroxyl end groups (INCI: amodimethicone), monomethylpolysiloxane with Lauryl frictionketten and polyoxyethylene and / or Polyoxypropylenendketten, (INCI: laurylmethicone copolyol), dimethylsiloxane / glycol Copolymeracetat (INCI: dimethicone copolyol
  • silicone polymers are dimethicones, cyclomethicones and dimethiconols. Mixtures of silicone polymers are also suitable, e.g. a mixture of dimethicone and dimethiconol.
  • the names given in brackets above correspond to the INCI nomenclature (International Cosmetic Ingredients), as they are intended for the labeling of cosmetic active ingredients and auxiliaries.
  • non-setting, nonionic polymers such as polyethylene glycols, non-setting, anionic and natural polymers and mixtures thereof in an amount of preferably 0.01 to 50% by weight.
  • Perfume oils in an amount of 0.01 to 5% by weight opacifiers such as ethylene glycol distearate in an amount of 0.01 to 5% by weight, Wetting agents or emulsifiers from the classes of anionic, cationic, amphoteric or nonionic surfactants such as fatty alcohol sulfates, ethoxylated fatty alcohols, fatty acid alkanolamides such as the esters of hydrogenated castor oil fatty acids in an amount of 0.1 to 30% by weight, as well as humectants, coloring agents, light stabilizers, antioxidants and Preservatives in an amount of 0.01 to 10% by weight.
  • opacifiers such as ethylene glycol distearate in an amount of 0.01 to 5% by weight
  • Wetting agents or emulsifiers from the classes of anionic, cationic, amphoteric or nonionic surfactants such as fatty alcohol sulfates, ethoxylated fatty alcohols, fatty acid
  • FIG. 1 schematically shows the process for producing a permanent hairstyle shape that can be called up.
  • a strand of hair is wound on a winding body and sprayed with a solution according to the invention containing a crosslinkable macromer.
  • a suitable energy source e.g.
  • the desired permanent shape is fixed with a UV lamp. Finally, the winding body is removed.
  • Figure 2 shows the deformation of a permanent hairstyle shape and restoration of the permanent shape from the temporary shape.
  • the curl in the permanent shape has the length lo •
  • the curl in the deformed shape has the length l.
  • the curl in the restored form has the length 1 2 •
  • the curl in the permanent shape has the length lo •
  • the curl in the deformed shape has the length l.
  • the curl in the restored form has the length 1 2 •
  • the memory factor can be used as a measure for assessing the shape memory properties of a composition, taking into account both the formability of a permanent hairstyle shape into a temporary shape (form factor) and the resetting of the permanent shape from the temporary shape (reset factor, degree of restoration). If a smooth streak is assumed, onto which a curl shape is impressed as a permanent shape and onto which a second, smooth shape is then impressed as a temporary shape, the shape factor can be determined according to the following criteria:
  • the reset factor can be determined according to the following criteria:
  • M (f / F) * (r / R) * 100
  • the memory factor should ideally not be less than 25, preferably between 25 and 33.3, particularly preferably between 37 and 100.
  • Example 1 Hair treatment with a thermoset shape memory polymer
  • Approx. 1 g of the composition was applied to straight strands of hair each 19 cm in length.
  • the strands were wound on curlers and dried.
  • the mixture was then heated to approximately 65 to 70 ° C. and cured photochemically (UV light; mercury lamp or facial tanner). After curing and cooling to room temperature, the winders were removed.
  • the curls (stamped permanent shape) had a length of 8 cm.
  • the curls were weighed down with a weight of 25 g each and hung out a) 1 hour, b) 2 hours and c) 3 hours at room temperature.
  • the lengths of the curls after deformation were a) 10 cm, b) 10 cm and c) 11.2 cm.
  • Examples 2 to 31 Hair treatment with shape memory polymer Compositions were prepared from 2% by weight of macromer in an ethanol / water mixture (50/50) with the following macromers or macromer mixtures with the following weight ratios
  • compositions 2 to 31 were used as described in Example 1 with similar results.
  • compositions were produced from 2% by weight of macromer in THF with the following macromers or macromer mixtures with the following weight ratios:
  • compositions 32 to 41 were used as described in Example 1 with similar results.
  • a composition was prepared from 2% by weight PLGA (7k) -DMA macromer in ethyl acetate and applied to the hair. After the hair was shaped, the shape was fixed by irradiation with UV light.
  • the shape memory polymers were produced from two different macrodiols and trimethylhexane-1, 6-diisocaynate analogously to Example 1 of WO 99/42147.
  • the hair treatment compositions were made from 0.5 wt% multiblock copolymer in a suitable solvent or solvent mixture such as e.g. Water, ethanol, tetrahydrofuran, chloroform or mixtures of these solvents, in particular
  • Tetrahydrofuran, chloroform or a water / ethanol / THF mixture Tetrahydrofuran, chloroform or a water / ethanol / THF mixture.
  • PLGA poly (L-lactide-co-glycolide)
  • PCL poly ( ⁇ -caprolactone)
  • the numerals in the names of the macrodiols each represent the approximate molecular weight of the macrodiols ( ⁇ 100)

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Abstract

L'invention concerne un procédé permettant d'obtenir une forme capillaire reproductible dans lequel une composition est appliquée sur les cheveux. Cette composition comprend au moins un agent actif qui, seul ou en association avec d'autres substances, peut conférer aux cheveux un effet mémoire de forme une fois qu'il a été appliqué sur les cheveux et que le traitement selon l'invention a été effectué. On donne aux cheveux une forme spécifique (permanente) puis cette forme permanente est fixée par induction d'une modification chimique ou physique des agents actifs appliqués, la forme mémoire initiale étant reproductible par stimulation physique après une déformation souhaitée ou non souhaitée de la forme mémoire. L'invention se rapporte en outre à un procédé permettant de reproduire une forme de coiffure permanente programmée antérieurement à laquelle on a provisoirement donné une forme temporaire ou qui a été déformée d'une quelconque autre manière.
EP03724997A 2002-04-10 2003-04-10 Procede permettant de produire des effets de memoire de forme sur des cheveux Withdrawn EP1492493A1 (fr)

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DE10215858A DE10215858A1 (de) 2002-04-10 2002-04-10 Verfahren zur Haarbehandlung mit Formgedächtnispolymeren
DE10215858 2002-04-10
DE2002128120 DE10228120B4 (de) 2002-06-24 2002-06-24 Mittel und Verfahren zur Haarbehandlung mit Formgedächtnispolymeren
DE10228120 2002-06-24
PCT/EP2003/003734 WO2003084490A1 (fr) 2002-04-10 2003-04-10 Procede permettant de produire des effets de memoire de forme sur des cheveux

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BR0304414A (pt) 2005-02-01
WO2003084490A1 (fr) 2003-10-16
BR0304411A (pt) 2004-07-27
JP2005527571A (ja) 2005-09-15
US20060140892A1 (en) 2006-06-29
JP2005529095A (ja) 2005-09-29
EP1492492A1 (fr) 2005-01-05
WO2003084489A1 (fr) 2003-10-16
AU2003227596A1 (en) 2003-10-20
AU2003224060A1 (en) 2003-10-20
US20050244353A1 (en) 2005-11-03

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