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EP1492494A1 - Methode de traitement capillaire au moyen de polymeres a memoire de forme - Google Patents

Methode de traitement capillaire au moyen de polymeres a memoire de forme

Info

Publication number
EP1492494A1
EP1492494A1 EP03724998A EP03724998A EP1492494A1 EP 1492494 A1 EP1492494 A1 EP 1492494A1 EP 03724998 A EP03724998 A EP 03724998A EP 03724998 A EP03724998 A EP 03724998A EP 1492494 A1 EP1492494 A1 EP 1492494A1
Authority
EP
European Patent Office
Prior art keywords
hair
macromer
amino
crosslinkable
shape
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Withdrawn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
EP03724998A
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
Application filed by MnemoScience GmbH filed Critical MnemoScience GmbH
Publication of EP1492494A1 publication Critical patent/EP1492494A1/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Withdrawn legal-status Critical Current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
    • A61K8/18—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
    • A61K8/02—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
    • A61K8/88—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 styling using 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. These styling products facilitate e.g. as a gel the shaping and creation of the hairstyle, as a hairspray improve the state of a created hairstyle and as a setting foam increase the volume of the hair. 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. The disadvantage is that due to the chemical treatment of the hair with reducing and oxidizing agents
  • Impairment of the hair structure cannot be avoided.
  • Another disadvantage of the previously known methods for hair reshaping is that it is not possible to undo reshaping in a relatively simple manner, i.e. to go from one hairstyle shape to another without time-consuming re-creation.
  • 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 described procedure for hair treatment corresponds to a treatment with a typical thermoplastic.
  • the hairstyle shape is created above Tg and fixed by cooling below Tg.
  • Tg glass transition temperature
  • the polymer softens and a new hairstyle can be created.
  • a method for a retrievable, reversible hair styling is not described.
  • the properties of linear polyurethanes are inadequate for an application for retrievable hair styling.
  • the object on which the present invention was based was to provide a method and the products required therefor for 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 - a composition which has at least one crosslinkable
  • Macromer which forms a shape memory polymer after crosslinking, is applied to the hair, the macromer a) containing crosslinkable regions which are crosslinkable by chemical bonds and b) contain thermoplastic areas which are not chemically crosslinkable, before, at the same time or afterwards the hair is broken into a certain (permanent) shape and - the shape is then fixed by chemical crosslinking of the macromer to form the shape memory polymer, the shape memory polymer at least has a transition temperature Ttrans.
  • Another object of the invention is a method for
  • 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 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.
  • 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) without outside
  • 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 preferably 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.
  • 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- lower the ratio of the elasticity modules and Ttrans i above st preferably at least 20.
  • the transition temperature Ttrans i 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 deformed or from the temporary form occurs.
  • 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 the elasticity at above or below the Ttrans-
  • the ratio of the moduli of elasticity below and above T trans i st 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), especially 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, polyacrylates, polyalkylenes, polyacrylamides, polyalkylene glycols, polyalkylene oxides, polyalkylene terephthalates, polyorthoesters, polyvinyl ethers, polyvinyl esters, polyester, polyvinyl halide, polyvinyl halide, polyvinyl halides, polyvinyl halides, polyvinyl halides, polyvinyl halides, polyvinyl , Polyurethanes and their copolymers.
  • suitable polyacrylates are poly (ethyl methacrylate), poly (ethyl methacrylate), poly (butyl methacrylate), poly (isobutyl 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.
  • 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; Polyorthoest
  • poorly biodegradable polymer segments are poly (methacrylic acid), poly (acrylic acid), polyamides, polyethylene, polypropylene, polystyrene, Polyvinyl chloride, polyvinylphenol and their mixtures and copolymers.
  • compositions according to the invention for. the hair treatment contain at least one of the above, too
  • Shape memory polymers crosslinkable macromers or prepolymers in an amount of preferably 0.01 to 25% by weight, particularly preferably 0.1 to 15% by weight in a suitable liquid medium.
  • the composition can be in the form of a solution, dispersion, emulsion, suspension or latex.
  • the liquid medium is preferably cosmetically acceptable and physiologically harmless.
  • 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 e.g. those of the general formula
  • R- (X ') n -A3 (II) where R stands for a monovalent organic radical, A3 for a reactive, chemically crosslinkable group and - (X') n- for a divalent, thermoplastic polymer or oligomer segment.
  • A3 is preferably an acrylate or methacrylate group.
  • the segment (X ') n preferably represents polyalkylene glycols, their monoalkyl ethers and their block copolymers, the
  • Alkylene groups are preferably ethylene or propylene groups and the alkyl groups preferably have 1 to 30 C atoms. Particularly preferred are mixtures of (A) polyalkylene glycols or polycaprolactones terminally esterified at both ends with acrylic or methacrylic acid and (B) terminally polyalkylene glycol monoalkyl ethers esterified with acrylic or methacrylic acid at one end, the alkylene groups preferably ethylene or propylene groups and the alkyl groups are preferably Cl to C30 alkyl groups.
  • component (A) are suitable, for example: 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.
  • 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 ones can also be used
  • Solvents are 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.
  • 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 nonionic, cationic, have an 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 be modified by the addition of other polymers with thickening effect in its hair-setting properties.
  • film-forming, hair-fixing polymers are understood to mean those polymers which, when used in 0.01 to 5% strength aqueous, alcoholic or aqueous-alcoholic solution, are capable of having one on the hair
  • Suitable synthetic, nonionic, film-forming, hair-fixing polymers in the hair treatment composition according to the invention are homopolymers of vinyl pyrrolidone, homopolymers of N-vinyl formamide, copolymers of vinyl pyrrolidone and vinyl acetate, terpolymers of vinyl pyrrolidone, vinyl acetate and vinyl propionate, polyacrylamides, polyvinyl amides, or polyglycol amides, or polyglycol amides Molecular weight of 800 to 20,000 g / mol can be used.
  • Suitable synthetic, film-forming anionic polymers include crotonic acid / vinyl acetate copolymers and terpolymers made from acrylic acid, ethyl acrylate and N-t-butyl acrylamide.
  • Natural film-forming polymers or polymers made therefrom by chemical conversion can also be used in the hair treatment composition according to the invention.
  • Amphoteric polymers can also be used in the hair treatment composition according to the invention. Are suitable for.
  • the cationic polymers which can be used according to the invention include copolymers of vinylpyrrolidone with quaternized derivatives of dialkylaminoacrylate and methacrylate, such as, for example, vinylpyrrolidone / dimethylaminomethacrylate copolymers quaternized with diethyl sulfate.
  • Further cationic polymers are, for example, the copolymer of vinyl pyrrolidone with vinyl imidazolium methochloride, the
  • the consistency of the hair treatment composition according to the invention can be increased by adding thickeners.
  • thickeners for example, homopolymers of acrylic acid with a molecular weight of 2,000,000 to 6,000,000 g / mol are suitable for this.
  • Copolymers of acrylic acid and acrylamide (sodium salt) with a molecular weight of 2,000,000 to 6,000,000 g / mol, sclerotium gum and copolymers of acrylic acid and methacrylic acid are also suitable.
  • 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 n-butane, isobutane and propane, or mixtures thereof, and also dimethyl ether or fluorohydrocarbons such as F 152a (1,1-difluoroethane) or F 134 (tetrafluoroethane) and, furthermore, gaseous at the pressures in question are present as blowing agents Blowing agents such as N2, 2 O and CO 2 and mixtures of the above-mentioned blowing agents are suitable.
  • 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 make it possible to spray a composition without using a propellant.
  • 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 container expanding and from which the agent continuously as a result of the contraction of the elastic container when the spray valve is opened is used.
  • 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 worked into the hair as a foam and without
  • 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 foam a Allow liquid with or without the use of a propellant.
  • a commercially available pump foamer or an aerosol foam head, for example, can be used 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 2 / s at 25 ° C., measured as a dynamic viscosity measurement with 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 axle 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 with 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.
  • those for cosmetic purposes can be used as alcohols used lower Cl to C4 alcohols such as 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 constituents which impart viscosity, in an amount of 0.1 to 10% by weight, or the required viscosity and creamy consistency is achieved by micelle formation with the aid of suitable emulsifiers , Fatty acids, fatty alcohols, waxes etc. in the usual way.
  • 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), 1-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-1- [(2-hydroxyethyl) amino] -2-nitrobenzene (HC RedNo.
  • Quinone dyes 1,4-di [(2, 3 -dihydroxypropyl) amino] -9, 10-anthraquinone, 1,4-di [(2-hydroxyethyl) amino] -9, 10-anthraquinone (CI61545, Disperse Blue 23) , 1- [(2-Hydroxyethyl) amino] - -methylamino-9, 10-anthraquinone (CI61505, Disperse Blue No.
  • Di (dimethylamino) phenothiazine-5-ium chloride (CI52015 Basic Blue No. 9), Di [4- (dimethylamino) phenyl] [4- (phenylamino) naphthyl] carbenium chloride (CI44045; Basic Blue No. 26 ), 2- [(4- (ethyl (2-hydroxyethyl) amino) phenyl) azo] -6-methoxy-3-methyl- benzothiazolium methyl sulfate (CI11154; Basic Blue No. 41), 8-amino-2-bromo-5-hydroxy-4-imino-6- [(3-
  • 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.
  • the 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.
  • the inorganic pigments can be of natural origin, for example made from chalk, ocher, umber, 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, gloss pigments, metallic effect pigments, pearlescent pigments and fluorescent or phosphorescent pigments, preferably at least one pigment being a colored pigment , 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 (Cl 77891), black iron oxide (Cl 77499), yellow iron oxide (Cl
  • 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, for example, the natural pigments sepia, rubber gut, bone charcoal, Kasseler brown, indigo, chlorophyll and other plant pigments.
  • Synthetic organic pigments are, for example, azo pigments, anthraquinones, indigoids, dioxazine, quinacridone, phthalocyanine, isoindolinone, perylene and perinone, metal complex, alkali blue and diketopyrrolopyrrole pigments.
  • 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 cation-active substances which, due to cationic or cationizable groups, in particular primary, secondary, tertiary or guaternary 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 with hydroxyl end groups (INCI: amodimethicone), monomethylpolysiloxane with lauryl side chains and polyoxyethylene and / or polyoxypropylene end chains, (INCI: laurylmethicone copolyol), dimethylsiloxane / glycol copolymer acetate (INCI: dimethoxanoxilyl copo
  • Trimethylsilyl end groups (INCI: trimethylsilylamodimethicone).
  • Preferred silicone polymers are dimethicones, cyclomethicones and dimethiconols. Mixtures of silicone polymers are also suitable, e.g. a mixture of dimethicone and dimethiconol.
  • 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.
  • 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.
  • Figure 2 shows the deformation of a permanent hairstyle shape and restoration of the permanent shape from the temporary shape.
  • the lock of hair in the permanent shape has the length lo •
  • the lock in the deformed shape has the length l ⁇ .
  • the curl in the restored form has the length I2 •
  • the memory factor in which both the formability of a permanent hairstyle shape into a temporary one, can serve as a measure for assessing the shape memory properties of a composition Form (form factor) as well as the resetting of the permanent form from the temporary form (resetting factor, degree of restoration) must be taken into account. 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
  • the composition applied.
  • 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.
  • 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 macromers used in Examples 2 to 42 were prepared in a manner analogous to that described in WO 99/42147.
  • MeO-PEG- (300) -MA methyl-poly (ethylene glycol) methacrylate
  • MeO-PPG (200) -MA methyl-poly (propylene glycol) methacrylate
  • PLGA (7k) -DMA poly (L-lactide-co- glycolide) -dimethacrylate
  • PCI (10k) -DMA poly ( ⁇ -caprolactone) -dimethacrylate

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Abstract

L'invention concerne une méthode de traitement capillaire permettant de réaliser une coiffure susceptible d'être recréée au moyen de polymères à mémoire de forme. Cette méthode consiste à appliquer sur les cheveux une composition contenant un macromère ou un prépolymère pouvant être réticulé pour former un polymère à mémoire de forme, à coiffer les cheveux pour réaliser une mise en forme (permanente) déterminée, puis à fixer cette mise en forme permanente par réticulation chimique du macromère ou du prépolymère de façon à former un polymère à mémoire de forme. Les macromères ou les prépolymères comprennent des régions réticulables par liaisons chimiques et des régions thermoplastiques non réticulables chimiquement. Les polymères à mémoire de forme présentent au moins une température de transition Ttrans. Une seconde mise en forme (temporaire) peut être réalisée en plus de la mise en forme permanente. L'invention concerne en outre un procédé permettant de recréer une mise en forme permanente lorsque les cheveux ont fait l'objet d'une seconde mise en forme temporaire ou lorsque la coiffure a été défaite d'une autre manière.
EP03724998A 2002-04-10 2003-04-10 Methode de traitement capillaire au moyen de polymeres a memoire de forme Withdrawn EP1492494A1 (fr)

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DE10215858 2002-04-10
DE10215858A DE10215858A1 (de) 2002-04-10 2002-04-10 Verfahren zur Haarbehandlung mit Formgedächtnispolymeren
PCT/EP2003/003735 WO2003084491A1 (fr) 2002-04-10 2003-04-10 Methode de traitement capillaire au moyen de polymeres a memoire de forme

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CA2501617C (fr) 2002-10-11 2012-04-24 Ronald A. Sahatjian Endoprothese extensible en polymere a memoire de forme
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AU2003282572B2 (en) 2002-10-11 2009-04-09 University Of Connecticut Crosslinked polycyclooctene
CA2501549C (fr) 2002-10-11 2011-08-30 University Of Connecticut Melanges de polymeres amorphes et semicristallins possedant des proprietes de memoire de forme
US7794494B2 (en) 2002-10-11 2010-09-14 Boston Scientific Scimed, Inc. Implantable medical devices
US7976936B2 (en) 2002-10-11 2011-07-12 University Of Connecticut Endoprostheses
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DE102005052140A1 (de) * 2005-10-28 2007-05-03 Henkel Kgaa Haarbehandlungsverfahren mit verbesserter Pflegeleistung sowie Vorrichtung und Mittel zur Durchführung des Verfahrens
EP1837160B1 (fr) * 2006-03-23 2011-12-07 Helmholtz-Zentrum Geesthacht Zentrum für Material- und Küstenforschung GmbH Polymères et compositions à mémoire de formes sensibles à une force ionique
JP5608226B2 (ja) * 2009-06-16 2014-10-15 スリーエム イノベイティブ プロパティズ カンパニー 剥離可能な接着物品
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JP2005529096A (ja) 2005-09-29
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AU2003227597A1 (en) 2003-10-20
US20060088494A1 (en) 2006-04-27

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